The ONLY proven, all-in-one system designed to help product marketers land their dream PMM job in as little as 30 days. The PMM Job Search System The ONLY proven, all-in-one system designed to help you land your dream product marketing job in as little as 30 days. Apply today APPLICATION CLOSES OCTOBER 3RD Built by a recognized PMM leader to guide you through every step of the job search process, from applications to interviews, assignments, and negotiations, with live group coaching and a supportive peer network. 300+ alumni have used this system to secure dream PMM roles in as little as 4 weeks at leading companies such as: 30-Day Money Back Guarantee Hundreds of PMMs have landed roles using this process. If you do the work and you don’t see the value in 30 days, I’ll refund you. Read full terms and conditions . Signs your job search strategy is not working: You apply to every new job you see posted, spending endless hours submitting applications, but not getting any responses. You repeatedly reach the interview stage but can’t seem to advance past the first round. You prepare answers for each interview, but leave feeling like you didn’t really “sell” yourself and your accomplishments. You keep getting rejected in favor of “more experienced” candidates, even when you suspect that’s not true. You find yourself getting to the final round but never seem to seal the deal. I know how draining this feels. That’s why I built a proven system to get you hired faster . Apply before Oct 3 and step into a new PMM role before 2026. Through this program, I was first able to land a great contract role at DoorDash within months, and then soon after, a full-time role as a PMM. It really IS that good. Austin Ng / Product Marketing Manager, DoorDash Susan Liu , Sr Product Marketing Manager, Semble "I was job searching on my own for 6 months with no results, and after enrolling in Yi Lin's program, I landed a role in 5 weeks . My only regret is not investing in this program sooner!" Carrie Silver , Product Marketing Manager, Digital Onboarding "I went from being stuck to landing my dream role at a fully remote company in less than 3 months. This was by far the best investment I made for my career!" Palma Tortorella Product Marketing Manager, Napo I enrolled in the PMM Job Search System in January 2025, and within just four months, I landed a new job. Before that, I had tried so many other resources and bits of advice, but nothing was working. Her program changed that. What stood out most were the detailed modules on positioning myself and the chance to watch real mock interviews, which completely transformed my approach. For me, this was a no-brainer investment. I feel lucky I took the leap, because it truly paid off! Jessica Shields Director of Product Marketing, Mastercard Before joining the PMM Job Search System in late 2024, I was getting interviews but couldn’t close the offer, despite my experience. After enrolling in the program, within 2 months I landed my DREAM role at a global brand. Specifically, this program gave me the structure and strategic edge I needed. Yi Lin’s frameworks and rubrics helped me sharpen how I tell my story and make it land interviews and peer examples pushed me to see my strengths more clearly and show up with impact. Yiwen Xu Staff Product Marketing Manager, Docker Job searching is a blend of science and art. It's for this reason that I was so happy with my decision to join Yi Lin’s job search program and community. The Science: Her structured frameworks and workshops provided a methodical approach to strategizing and refining my job search. The Art: Whenever I had specific questions or needed to bounce ideas, Yi Lin and community members actively contributed their experiences and expertise. As a result, I went from not receiving any interviews to finally reaching the hiring manager rounds and final rounds and eventually securing my dream role as Staff Product Marketing Manager. I highly recommend enrolling in her program. You won’t regret it! Brandon Hatter Senior Product Marketing Manager, AssetWatch Yi Lin’s expertise was invaluable in helping me stand out in a crowded PMM job market. Her feedback was direct yet kind, giving me the edge I needed to progress in interviews. The Courageous Careers community she’s built is equally powerful - generous, insightful, and supportive. Working with Yi Lin was one of the best career decisions I’ve made. In my latest job search, by using her process, I landed a great Sr PMM role in just 3 weeks. Casey Ohashi Sr Product Marketing Manager, Attain Yi Lin’s deep expertise and unparalleled understanding of today’s PMM career landscape were instrumental in helping me identify and secure an exciting role that aligns perfectly with my career goals in less than a month . Her course is comprehensive, tackling every aspect of the increasingly complex recruitment and interview process. If you’re serious about advancing your PMM career and ready to take the next step, I can’t recommend Yi Lin's program highly enough. Angelica Navarro Product Marketing Manager, Sortly In Yi Lin's program, I got a wealth of incredible resources to help me interview well, ask the right questions, and ace interview assignments. With hard work and help from Yi Lin, I landed a role that feels like the RIGHT role for me and is also a bump in title! Yi Lin and her community of fellow PMMs were there for me through every step of my journey. I felt seen, heard, and supported—on the days when I was feeling not-so-great, I never felt alone. I can't recommend her program enough! Valentyna Havryliuk Sr Product Marketing Manager, SE Ranking I enrolled in Yi Lin’s program in January 2025, and in just 1.5 months, I landed a top-tier PMM role. Before Yi Lin’s program, I struggled to position myself effectively as was not getting the results I needed. Going through her strategies on targeting and positioning helped me refine my strengths, target the right companies, and craft a results-driven narrative that set me apart. In addition, the program’s numerous frameworks, community, and accountability kept me focused, and supported and was a huge game changer from job searching alone. If you’re serious about landing the right job, this program is the best investment you can make … as it certainly paid off for me. Heather Ryan Director of Product Marketing, Workiva I’d been a multi-time founding PMM, ready to leave startups for a later-stage company. Four months after joining Yi Lin’s PMM Job Search System, I landed an incredible IC Director role at a public company. I’d worked with other coaches, but nothing compared to the clarity, depth, and actionable guidance here. The program gave me a step-by-step roadmap for today’s job market, targeting the right companies, refining my materials, nailing interviews, and negotiating offers. If you’re serious about leveling up your PMM career, this is the real deal. I’ve already recommended it to friends. Sabari Sawant Product Marketing Manager, AWS I wholeheartedly recommend Yi Lin's job search program. After enrolling in her program and joining her community, I landed a great job in 2 months ! One exceptional member of Yi Lin’s community (a former client of hers) provided generous support to help me with mock interviews. Other members also went out of their way to provide me with referrals and gave insightful guidance on their experiences, which led me ultimately to victory. Klarissa Djajalie Product Marketing Manager, UserCentric I was landing screening interviews but wasn't advancing so I joined Yi Lin's Program, and I am so glad I did! The program really helps you rethink your experience and work on your messaging and positioning for yourself, and the community is truly one of the most supportive and motivating communities of PMMs and aspiring PMMs out there. I've since landed an offer, and I couldn't thank Yi Lin and the community enough for the support in the job search process and helping me find my confidence again. Greta Swanson Director of Product Marketing, AACR After being laid off, I knew I needed more than just a solid resume and a recruiter screen to stand out. Yi Lin’s program gave me the tools, structure, and support I was missing. Her modules are incredibly thorough and walk you through everything: refining your resume, writing strong cover letters, optimizing your LinkedIn profile, preparing for interviews and assignments, negotiating offers, and even setting yourself up for success in the first 90 days. Yi Lin herself is a gem: smart, warm, incredibly helpful, and genuinely invested in your success. I am glad I found this program! Khuslen Khosbayar Associate Product Marketing Manager, Kong Yi Lin's program has been an incredibly enriching experience for me. Though I initially entered the program hoping to land my next role (which I did!), I quickly realized that this program offered much more than just the promise of a new position, thanks to the carefully designed workshops, along with the active community she fostered. Going into my new role, I will keep in touch with the fantastic people I've met in the community! Thank you, Yi Lin, for fostering such a supportive and active community through your awesome program! Gal Perelman Product Marketing Lead, Unit 21 As someone who didn't work much in the US, I felt stuck and struggled to move forward. When I reached out to Yi Lin, I could immediately see the results. Her program and community provided incredible value, including training sessions, live feedback, and workbooks. With these resources, I was able to land multiple interviews, pass the entire process, and score several PMM offers! Her help was life-saving, and her feedback, approach, and methodology are PRICELESS. I learned so much about communicating my story to others professionally. I would recommend Yi Lin's PMM to any PMM! Adam Miller Solutions Marketing Manager, Ellucian I can't say enough about how much I love the Courageous Careers community. Whenever I post a question, community members quickly jump in and help me get the answers I need on any topic. As any job-seeker knows, final projects are grueling and tough to nail. But with the help of the Courageous Careers community, I greatly improved my presentation that helped me land an offer. Yi Lin also hosts awesome workshops that have helped me upskill in my interview skills. Every time I attend, I know I'll leave with a ton of value. I'm so thrilled to be here! Yiwen Xu Staff Product Marketing Manager, Docker Job searching is a blend of science and art. It's for this reason that I was so happy with my decision to join Yi Lin’s job search program and community. The Science: Her structured frameworks and workshops provided a methodical approach to strategizing and refining my job search. In particular, Yi Lin’s advice on writing a cover letter in the application to stand out in this competitive market and her multi-step interview prep guide were gold. The Art: Whenever I had specific questions or needed to bounce ideas, Yi Lin and community members actively contributed their experiences and expertise. Their words of encouragement and willingness to share their own vulnerability made the journey less lonely. As a result, I went from not receiving any interviews to finally reaching the hiring manager rounds and final rounds and eventually securing my dream role as Staff Product Marketing Manager. I highly recommend enrolling in her program. You won’t regret it! Casey Ohashi Sr Product Marketing Manager, Attain Yi Lin’s deep expertise and unparalleled understanding of today’s PMM career landscape were instrumental in helping me identify and secure an exciting role that aligns perfectly with my career goals, in less than a month. Her course is comprehensive, tackling every aspect of the increasingly complex recruitment and interview process. In my experience, and as Yi Lin advises, preparation is by far, the biggest key to succeeding in interviews. Yi Lin ensures you’re as prepared as possible. If you’re serious about advancing your PMM career and ready to take the next step, I can’t recommend Yi Lin's program highly enough. Angelica Navarro Product Marketing Manager, Scorpion Last year, after leaving a company that was not a good fit for me, I was feeling unsure, discouraged, and stuck. Being in Yi Lin's program helped me boost my confidence, identify my superpowers, turn myself into a "product," and market myself to potential employers effectively. Eventually, I got further and further into interview stages and finally, presentations and projects. In Yi Lin's program, I got a wealth of incredible resources to help me interview well, ask the right questions, and ace interview assignments. With hard work and help from Yi Lin, I landed a role that feels like the RIGHT role for me and is also a bump in title! Yi Lin and her community of fellow PMMs were there for me through every step of my journey. I felt seen, heard, and supported—on the days when I was feeling not-so-great, I never felt alone. I can't recommend her program enough! Valentyna Havryliuk Sr Product Marketing Manager, SE Ranking I enrolled in Yi Lin’s program in January 2025, and in just 1.5 months, I landed a top-tier PMM role. Before Yi Lin’s program, I struggled to position myself effectively as was not getting the results I needed. Going through her strategies on targeting and positioning helped me refine my strengths, target the right companies, and craft a results-driven narrative that set me apart. In addition, the program’s numerous frameworks, community, and accountability kept me focused, and supported and was a huge game changer from job searching alone. If you’re serious about landing the right job, this program is the best investment you can make … as it certainly paid off for me. Sabari Sawant Product Marketing Manager, AWS I wholeheartedly recommend Yi Lin's job search program. After enrolling in her program and joining her community, I landed a great job in 2 months! All of the expertise and resources, along with her dedication, set her uniquely apart as a coach and mentor . Specifically, immediately after working with her, I diligently followed all her advice, from how to format my resume to how to prepare for each interview - this helped simplify at least half of the preparation process for me and immediately transformed my interview outcome. In addition, Yi Lin’s job search community proved transformational for me. One exceptional member of Yi Lin’s community (a former client of hers) provided generous support to help me with mock interviews . Other members also went out of their way to provide me with referrals and gave insightful guidance on their experiences, which led me ultimately to victory. Klarissa Djajalie Product Marketing Manager, UserCentric I was landing screening interviews but wasn't advancing so I joined Yi Lin's Program, and I am so glad I did! The program really helps you rethink your experience and work on your messaging and positioning for yourself, and the community is truly one of the most supportive and motivating communities of PMMs and aspiring PMMs out there. I've since landed an offer and I couldn't thank Yi Lin and the community enough for the support in the job search process and helping me find my confidence again. Khuslen Khosbayar Associate Product Marketing Manager, Kong Yi Lin's program has been an incredibly enriching experience for me. Though I initially entered the program hoping to land my next role (which I did!), I quickly realized that this program offered much more than just the promise of a new position , thanks to the carefully designed workshops, along with the active community she fostered. Going into my new role, I will keep in touch with the fantastic people I've met in the community! Thank you, Yi Lin, for fostering such a supportive and active community through your awesome program! Read 80+ Testimonials on LinkedIn (Recommendations Section) I’ve coached hundreds of PMMs, so I’ve seen job seekers making the same mistakes over and over - mistakes that are keeping them from landing their dream roles sooner: ❌ You’re using a “spray and pray” approach with applications, hoping something sticks. ❌ You struggle to translate your experiences from another sector or role in a compelling way. ❌ You don’t know how to position yourself as the ideal candidate and don’t know what hiring managers really want. ❌ You’ve got great experience, but your stories fall flat or meander during interviews. ❌ You’re unsure how to drive interview conversations to demonstrate executive presence. ❌ You’re missing the mark on your assignment/case study and don’t know where you’re doing wrong. ❌ You don’t have the first clue how to talk about – or even USE – AI skills in the interview process. ❌ You lack confidence in your ability to succeed in a competitive job market. Here's the truth: interviewing without the right guidance is like studying for an exam without knowing the subject. And in today’s market, the exam is even harder. Moreover, hiring managers are now using AI both to shape their interview questions AND ask directly about your AI skills and approaches. If you’ve ever walked away from an interview questioning what went wrong or feeling lost about what hiring managers are looking for, this program is for you. You’ll identify the blind spots holding you back, then get practical, personalized steps to course-correct, including how to navigate AI-driven interview trends. Relying on ChatGPT alone is a losing game because you end up sounding like everyone else in the moment that you NEED to stand out the most. But with insights from over 300 successful alumni, a network of mentors, and a proven rubric to guide you, you’ll finally see what hiring managers are looking for. Get the insider knowledge you wish you’d had from the start, and make your next interview your last. Apply Today Core Curriculum 30+ bite-sized on-demand lessons across 9 actionable modules Templates, guides, and real-world examples from successful PMMs Step-by-step frameworks covering applications, interviews, assignments, and negotiations Module 1: Your Winning PMM Job Search Strategy Replace guesswork with a proven, repeatable system that lands more interviews in less time. Introduction & what to expect Master the proven strategy to apply for fewer roles and land more interviews. Uncover the real reasons companies hire and what hiring managers truly look for (insights you won’t find elsewhere). [BONUS] Build efficient job search habits with the PMM 30-Day Job Search Guide and Job Search Tracker [templates included] Module 2: Define Your Ideal Company Profile (ICP) Stop applying to every opening. Learn how to zero in on the right companies and roles where you’ll actually stand out. Identify your unique value and competitive edge with a tailored, step-by-step framework to focus on companies that match your strengths. Build laser-focused messaging aligned with your ICP, supported by a personal messaging house [template included]. Module 3: Craft a Hyper-Targeted Resume Tired of sending your resume into a black hole? Build a resume that makes your value impossible to ignore. Follow a step-by-step guide to create value-driven, keyword-optimized resumes that both ATS and hiring managers love [resume template included] . Write concise, impactful bullet points that translate your experience into interview opportunities. [BONUS] Gain practical insights with a live resume demo. Module 4: Develop a Cover Letter & LinkedIn profile that converts Don’t rely on your resume alone. Show up as the obvious choice with materials that demand attention. Avoid the mistakes that instantly get cover letters tossed aside. Use a proven 3-part framework to write cover letters that win interviews [template included] . Apply LinkedIn tips to turn your profile into an interview magnet [template included]. Module 5: Apply the Right Way to Land Interviews Learn the smart way PMMs land interviews, without wasting hours on job boards Master PMM networking techniques to secure referrals that turn into real interviews [guide included] . Learn how to conduct informational interviews that genuinely advance your job search. Build a modern, tailored portfolio with step-by-step guidance, plus real critiques of actual portfolios so you know what works today. [New!] Discover creative outreach methods to stand out from the crowd. Simeon Atkins, Sr PMM at Mention Me "Before, I struggled to present my experience in a way that stood out to hiring managers. After utilizing Yi Lin’s approach, I secured a first-round interview for 1 in every 5 applications and landed a Senior PMM role with a salary increase at my top-choice company." Module 6: Ace Your Interviews Stop rolling the dice on interviews. Master a proven playbook to walk in confident and walk out with offers. Follow my proven Interview frameworks to craft strong, structured responses to behavioral, technical, and case questions. Master nerve control by learning quick methods to stay calm and focused. Streamline prep with the Interview Workbook: Use this easy-to-follow alumni favorite to prepare effectively [workbook included] Stand out with reverse interview questions by leading conversations confidently with execs using my curated questions [guide included] [BONUS] NEW! Get real-time coaching and curated answers with my AI Interview Copilot, built from real coaching calls. [BONUS] Sample Answers to the 8 Toughest Interview Questions. [BONUS] Watch 11 Mock Interviews with Real PMMs (from new PMMs to directors) to see strategies in action (priceless) Module 7: Create Stand-Out Assignments Most candidates see assignments as busywork. Turn them into your secret weapon to outshine the competition. Gain a competitive edge with a systemized approach to PMM assignments [guide included] . Beat more experienced candidates by understanding exactly how your assignment will be scored using the scoring rubric [rubric included] . Take the guesswork out and know exactly how to stand out with a step-by-step assignment walk-through. BONUS: Get 3 real-life assignments from past alumni (priceless) Module 8: Negotiate Your Worth Before you say “yes!”, learn the exact approach alumni used to boost their salaries by $50K – and how you can too. Learn the negotiation strategy that has helped past alumni achieve salary increases of up to $50K. Use my proven 'Closing Method' templates to make a compelling ask [template included] . Discover how to negotiate beyond salary for added benefits and perks. "Following Yi Lin’s advice, I was able to negotiate a higher salary, even after getting laid off. The investment in her program immediately paid off, and MORE." Jordan Adler, Product Marketing Manager at Kick-Up Module 9: Thrive in Your First 90 Days Don’t rely on your company’s onboarding plan! Start your new role with confidence, not confusion, and make an impact from day one. Make an impact from day one with my 30-60-90 day onboarding strategy. [template and checklist included] Learn and avoid the common mistakes PMMs make when onboarding. Beyond the Lessons: Resources That Give You An Edge In addition to the structured lessons, you’re also getting a complete toolkit packed with extras that accelerate your job search, keep you accountable, and make sure you don’t do this alone. Bonus 1 Monthly live coaching support Get exclusive access to monthly live group coaching calls where I guide PMM job seekers to solve challenges, share wins, and stay on track. In these sessions, you’ll: Get real-time answers directly from me: Bring your questions on resumes, interviews, or negotiations - I'll provide clear, actionable guidance Learn from fellow PMM job seekers: Connect with a supportive group, sharing insights and celebrating wins together Stay accountable and motivated: Regular check-ins keep you on track and energized Best of all, you can keep attending until you land a job , ensuring you have all the support you need to reach your career goals. Bonus 2 AI Interview Copilot [NEW! ] Practice smarter with an exclusive AI copilot interview partner I’ve designed from my real PMM coaching sessions, not generic prompts. With the AI Copilot, you’ll: Rehearse with confidence: Run mock interviews using a proven 7-step process tailored to PMM roles. Get expert-backed feedback: Access critiques and insights drawn from hundreds of real coaching calls. Stay sharp on new trends: Prepare for AI-shaped interview questions and competency checks that hiring managers now use. Because I’ve built and continue to refine this tool specifically for product marketers, and because it learns more about you as you use it, you won’t sound like everyone else using generic AI tools. You’ll craft and hone compelling, authentic answers that help you tell YOUR unique story to interviewers. Bonus 3 A Private, Supportive Community Just for You Join an exclusive Slack community of 300+ alumni and peers who’ve been where you are and know how to help. Tap into collective experience: Get insights and advice from others who’ve successfully navigated their job searches. Unlock exclusive job opportunities: Be the first to access roles from this personal network and get referrals. Build a lasting network: Form friendships and connections that go beyond job searching. This isn’t just another online group. Our community has been a launchpad for countless PMM careers, helping alumni land jobs through referrals, support, and shared resources. Bonus 4 A Buddy System Built for Real Progress No more awkward solo prep or winging it! Get matched with a practice buddy who makes interview prep feel structured, supportive, and confidence-boosting. With our buddy system, you’ll gain: Support and accountability: Practice with someone equally motivated to land a role, keeping each other on track. Authentic feedback: Get insights that help you see your strengths and growth areas clearly. With a buddy by your side, you'll have the encouragement and feedback needed to elevate your interview game and move closer to your dream job. Bonus 5 The PMM 30-Day Job Search Guide (on Notion) Take control of your job search with this step-by-step guide, designed to map out every task you need to complete throughout the bootcamp. Program participants love the clear, daily actions it provides, showing you exactly what to do each day for maximum success in your job search journey. Bonus 6 Exclusive PMM Masterclasses & Workshop Recordings Access live workshop recordings to learn from peers, and best practices for leveling up as a PMM. Live workshops and recordings include: Positioning and messaging (3-part, 4.5 hours) Product launch strategy 101 (1 hour) How to get promoted (1.5 hours) Monthly job search AMA recordings Apply Today Here is everything you will get in the PMM Job Search System: 30 impactful lessons/resources across 9 actionable modules .................................................... (value $3,499 ) packed with exclusive PMM job search content, templates and guides Real client mock interviews and assignments pack you won’t find anywhere else .................. (value $1,999 ) Lifetime access ....................................................................................................................................... (priceless ) [BONUS] Monthly live coaching until you land a job ......................................................................... (value $995 ) [BONUS] Private Slack group until you land a job, with access to 200 alumni and peers .............. (value $995 ) Friends for life ......................................................................................................................................... (priceless ) [BONUS] Curated buddy system ......................................................................................................... (value $1,495 ) for accountability and feedback to accelerate your learning and not feel alone [BONUS] The PMM 30-Day Job Search Guide ......................................................................................... (value $49 ) (on Notion) to keep you organized and on-track [BONUS] Access to exclusive PMM fundamentals masterclasses ............................................. (value $1,995 ) to make you a better PMM [BONUS] Custom-built AI interview co-pilot ...................................................................................... (value $595 ) designed specifically for PMM interviews, based on real interview recordings and coach feedback [GUARANTEE] 30-day refund policy ......................................................................................................... (priceless ) if you aren’t satisfied with your experience (200+ alumni doubt it!) Total Value: $11,622 Your investment: $1,095 Or 3 payments of $425 Apply Now Before application closes on October 3, 2025. Or 3 payments of $425 $11,6227 30 impactful, bite-sized lessons across 9 actionable modules packed with exclusive PMM job search content, templates and guides (value $3,499 ) Real client mock interviews and assignments pack you won’t find anywhere else (value $1,999 ) Lifetime access (priceless ) [BONUS] Monthly live coaching until you land a job (value $995 ) [BONUS] Private Slack group with access to 200 alumni, mentors, and peers (value $995 ) Friends for life (priceless ) [BONUS] Curated buddy system for accountability and feedback to accelerate your learning and not feel alone (value $1,495 ) [BONUS] The PMM 30-Day Job Search Guide (on Notion) to keep you organized and on-track (value $49 ) [BONUS] Access to exclusive PMM fundamentals masterclasses to make you a better PMM (value $1,995 ) [BONUS] Custom built AI interview co-pilot designed specifically for PMM interviews, based on real interview recordings and coach feedback (value $595 ) [GUARANTEE] 30-day refund policy if you aren’t satisfied with your experience (200+ alumni doubt it!) (priceless ) Apply Now Before Enrollment Closes on Oct 3 Your investment: $1,095 Here is everything you will get in the PMM Dream Job System: Total Value: More Testimonials Gal Perelman Product Marketing Lead, Unit 21 As someone who didn't work much in the US, I felt stuck and struggled to move forward. With Yi Lin's program, I was able to land multiple interviews, pass the entire process, and score several PMM offers! Her help was life-saving, and her feedback, approach, and methodology are PRICELESS. Adam Miller Solutions Marketing Manager, Ellucian I can’t say enough about how much I love the Courageous Careers community. It’s supportive, empathetic, and valuable for PMMs at any stage, from veterans to job seekers. Whenever I post a question, members quickly jump in with helpful, actionable answers. The community was pivotal in helping me ace a tough final project, giving me feedback that made my presentation far stronger than if I’d done it alone. Yi Lin’s workshops are equally impactful, every session leaves me with new skills and confidence as a PMM. I’m so glad I found this community and highly recommend it to anyone looking to grow, land a role, or level up their career. Liz Gorson Product Marketing Manager Working with Yi Lin has been one of the most impactful career decisions I’ve made. She helped me refine my positioning, target the right roles, and I landed my first interview within days. Unlike generalist coaches or courses, her guidance is tailored to the PMM market, practical, and immediately effective. Her mix of job search strategy, PMM expertise, and mindset coaching gave me confidence and clarity throughout the process. This program is Worth every bit of the investment. Raniz Bordoloi Product Marketing Manager, Stealth AI Startup I’ve worked with Yi Lin three times, and each engagement made me sharper about what I want and how to get there. Most recently, in just two months, I streamlined my search, refined my narrative, and navigated 20+ interviews to multiple offers, ultimately landing a founding PMM role at an AI-native startup. Yi Lin has a rare ability to cut through noise, pinpoint true candidate–market fit, and keep you focused on the right opportunities rather than the shiny ones. Robin Yee Product Marketing Manager, Thomson Reuters I can’t thank Yi Lin enough for her support and expertise. As an underdog in a tough market, I needed someone who truly understood PMM, and she delivered. She helped me sharpen my positioning, refine my storytelling, and target the right opportunities, leading to an offer in just three months. More importantly, she believed in me when I doubted myself, pushing me to show up with confidence. Her world-class PMM knowledge, proven frameworks, and caring approach gave me the edge I needed. I didn’t just land a new role, I became a stronger PMM. Amulya Vadrevu Product Marketing Manager, HoneyStack Yi Lin’s approach to resume writing completely transformed how I think about the recruiting process. She helped me shift from simply listing responsibilities to telling a compelling, results-driven story. Her insights gave me clarity and confidence, and I landed a role within months of joining her program. I can't recommend her enough! Read 80+ Testimonials on LinkedIn (Recommendations Section) FAQs What happens after I apply? Here’s how it works: Fill out a quick application (5 minutes) so I can learn your goals. Get accepted + onboard with a personal 1:1 kickoff session directly with me. Unlock immediate access to the full program, templates, and bonuses. Join live coaching + community with monthly group calls, an accountability buddy, and a Slack network of 300+ PMMs. Why do I need to apply? I review every application to make sure participants are motivated and a great fit. This keeps the cohort high-quality and ensures you’ll be surrounded by peers who are just as committed as you. What happens after 30 days? After 30 days, you keep access to all resources, monthly live Q&A sessions, the community, and your buddy. Your journey doesn’t end here, you’ll have ongoing support every step of the way until you land your dream job. Do you have a refund policy? Yes, I offer a 30-day money-back guarantee . If you watch at least 80% of the lessons, complete the exercises, apply for jobs, attend interviews, and still don’t find value, I’ll refund your money. Note that I can’t guarantee job placement in 30 days, but previous alumni have found roles quickly with this system. We’re confident you’ll find it worthwhile. This guarantee doesn’t apply if you stop job searching or don’t fully engage. How does the AI copilot work? Is it just a ChatGPT prompt? Not at all. The copilot isn’t merely a generic AI prompt; rather, it’s an interview partner I designed (and continue to refine) exclusively to accompany this course. It is informed by countless real (not AI) coaching interactions and call recordings with product marketing job seekers just like you. It takes you through my 7 processes, includes baked-in critiques from me, and allows for mock interview practice. Think of it as a practice partner; it delivers my critiques, frameworks, and prompts in real time, so you can run mock interviews and refine your answers. Best of all, because it’s tailored to PMM interviews and customized with your unique information, it ensures you sound confident and compelling, WITHOUT using the dry, cookie-cutter answers generic AI tools tend to produce. How much does it cost? Is there a payment plan? The full price is $1,095, or 3 payments of $425. Most alumni report a 10x ROI through faster job placement and higher salaries. Is this a course? No. It’s a complete program that blends self-paced lessons, live monthly coaching, an AI interview copilot, and a private Slack community. It’s more like an ecosystem than a course. How does the buddy system work? You’ll be paired with another participant with similar goals and experience to support each other and stay accountable. If your buddy lands a role, you can be matched with a new one. What commitment is required? You can go as quickly or leisurely as you’d like. Even with a busy schedule, you can succeed with around 60 minutes a day for job searching. Can’t I just do this myself with free content? If you could, you likely would have already. This system is structured to give you a clear, proven path that free content doesn’t provide. What is your participants’ success rate? What kinds of job seekers are most likely to succeed with the program? My clients see results when they commit to the full process, not just one piece of it. This isn’t an “à la carte” course; it’s a step-by-step system designed to work when you use it across every stage of your job search . By doing this, over 300 PMMs have trusted this framework to land new roles. In just 6 months 35 hires were tracked, that’s an average of one PMM per week landing a job . Many alumni cut their job search time dramatically – from months to weeks – and they share real stories and takeaways to help new members follow in their footsteps. Stop the dread. Land your dream job before 2026. Apply Now Land Your Dream PMM Job in 30 Days—Risk Free

At Courageous Careers, I help ambitious PMMs land and thrive in their dream jobs, and help PMM leaders turn chaos into clarity, strategy, and results. Product Marketing Coaching and Advising Get unstuck, grow with confidence, and lead with impact. I help ambitious PMMs land and thrive in their dream jobs, and PMM leaders turn chaos into clarity, strategy, and results. Book a Free Consult See Services As heard on : Recognitions: Hi, I’m Yi Lin Pei, 3x PMM leader, mom of two, and founder of Courageous Careers. Product marketing demands clarity, strategy, and influence, yet most PMMs are left guessing, juggling unclear expectations and contradictory advice. If you’re here, you might be facing one of these challenges: You’ve stepped into a new PMM or leadership role , and imposter syndrome is creeping in. You’re leading a team and want to uplevel your team performance, drive meaningful impact, and successfully tackle high-stakes projects in an ever-changing environment. You’re in a competitive job market and struggling to stand out and land the right role. Sound familiar? You’re not alone, and you’re in the right place. I’ve helped 200+ product marketers and dozens of leaders reach their career goals and drive business impact with all the confidence and none of the burnout. So, let’s get you unstuck and moving forward. I’ve supported 200+ clients at companies including: Ebun Onagoruwa Senior Vice President of Brand & Product Marketing “As a product marketing leader stepping into a new org, I was looking for a trusted thought partner, someone who could challenge my thinking . Yi Lin was exactly that. She’s a steady, strategic presence with sharp instincts and no patience for fluff, equally effective in navigating org design, go-to-market strategy, launch excellence, and the day-to-day realities of leading a large team. She brought valuable frameworks, and as a respected voice in the broader product marketing community, her published work gave me a helpful external lens to pressure-test our approach. Yi Lin is incredibly responsive, curious, a natural problem-solver, and always willing to help. What sets her apart is her ability to cut through noise, surface core issues quickly, and offer practical, high-leverage advice grounded in real-world experience. Her input helped me move faster and lead with greater clarity. I highly recommend working with Yi Lin." Here is how I can help: 1-1 Coaching Services Get the most personalized support at every critical stage of your PMM journey. Best for: PMMs at all career stages Explore the program that fits you best: Land Your Dream Job Ace Your New Job Thrive in Your Career Group Job Search Program Land your dream job without the 1:1 price tag. This course combines a proven job search system, monthly group coaching, and a vibrant community. Best for: New & mid-career PMMs Learn More Advising and Consulting Get 1:1 strategic advising, team training, or embedded fractional support to scale your team’s impact. Best for: Heads of product marketing and marketing leaders Learn More What clients say about working with me: Angie Ennamorato Product Marketing Manager, Deepki Going from a team of product marketers to a tech startup’s first dedicated PMM role was a big transition for me. I knew I needed help in my new role from someone who had done something similar to navigate my role successfully. Yi Lin brought in amazing qualities as a coach—perspective, wisdom, and empathy (to name a few)—that propelled me to a new phase of my career and job where I felt empowered to tackle opportunities and challenges. I would strongly recommend her to other product marketers who want to learn how to grow in their PMM careers, harnessing the value of their experience in a new environment. Maryann Akinboyewa Principal Product Marketing Manager, Hubspot Yi Lin provided support and guidance every step of my job search journey. She broke down exactly what to expect and how to best approach each stage of the interview process. There is no fluff with Yi Lin as she offered practical career advice that can be implemented immediately. Yiwen Xu Staff Product Marketing Manager, Docker With Yi Lin's program, I went from not receiving any interviews to finally reaching the hiring manager rounds and final rounds and eventually securing my dream role as Staff Product Marketing Manager. I highly recommend enrolling in her program. You won’t regret it! Robin Yee Product Marketing Manager, SafeSend As an underdog in this competitive market, I needed a coach who truly understood product marketing inside and out, and Yi Lin was that and more. She helped me sharpen my positioning, refine my storytelling, and target the right opportunities, ultimately leading to my job offer in just three months . But beyond strategy, she believed in me when I was in doubt, pushing me to show up with confidence. What differentiates her is her world-class product marketing knowledge, and her unmatched ability to break down what actually works in today’s job market. I came out of this experience not just with a new role, but as a stronger PMM. If you get the chance to learn from Yi Lin, take it. You won’t find a better mentor or coach. Raniz Bordoloi Product Marketing Manager, Go1 As a high achiever, I used to think career growth followed an obvious, linear path: get promoted, land a higher-paying job. While those are valid goals, I realized I needed more than external success. I wanted a career that felt truly fulfilling. That’s when I sought out Yi Lin for leadership coaching. Through many insightful sessions, Yi Lin helped me gain real career clarity. I went from feeling unmotivated to discovering a direction that energizes me , one that aligns with my strengths, values, and professional goals. Beyond finding this clarity, she also guided me to excel in key areas of product marketing and set me up for success in my role with greater confidence. I couldn’t be more grateful for her coaching! Peter Nakamura Sr Product Marketing Manager, Achievers Yi Lin has been a fantastic career coach and resource for me over the past year. Her depth of experience in the Product Marketing space allows her to quickly identify areas of opportunity and growth. Our work has been primarily focused on advancing my career as a PMM and she's helped me uncover new ways of thinking and approaching my career development. Yi Lin is kind and thoughtful while also being direct with her recommendations which is a rare combination! Her PMM community has also been a game changer as I get to learn about the latest in the space and connect with other brilliant PMMs. Angelica Navarro Product Marketing Manager, Scorpion In Yi Lin's program, I got a wealth of incredible resources to help me interview well, ask the right questions, and ace interview assignments. With hard work and help from Yi Lin, I landed a role that feels like the RIGHT role for me and is also a bump in title! Yi Lin and her community of fellow PMMs were there for me through every step of my journey. I felt seen, heard, and supported—on the days when I was feeling not-so-great, I never felt alone. I can't recommend her program enough! Stephanie Watshon Product Marketing Manager, Deloitte Yi Lin is an incredible career coach. She can help you identify your dream job, apply and interview for it, and then coach and develop yourself professionally once you’ve landed it. Her clients have the opportunity to collaborate and network with each other, and she’s built a strong and supportive PMM community around her business. With Yi Lin’s program, I accepted an offer within only one month of job hunting. I couldn’t recommend working with her more! Carley (Bohnen) Stugelmayer Director of Product Marketing, A-Lign Yi Lin was instrumental in my transition from an individual contributor to a director role in product marketing. Her deep expertise helped me not only refine our PMM processes, covering product launches, positioning, and messaging, but also build the critical cross-functional relationships needed to drive impact at the director level. After working with her, I feel more confident tackling high-stakes decisions and have greater clarity on my long-term career path. I’m incredibly grateful for her guidance! Allison Sands Sr Product Marketing Manager, Personio Working with Yi Lin flipped the script on how I approached my career. I went from feeling reactive to intentional. I felt confident and truly in control. She provided pragmatic frameworks that made everything seem more achievable, which gave me the confidence in my ability to lead, make strategic decisions, advocate for myself – and actually enjoy the process. What sets Yi Lin apart is that she’s not just an expert in product marketing—she’s actively shaping its future. She challenges conventional thinking, pushes you outside your comfort zone, and helps you see opportunities where you might have only seen obstacles. Brandon Hatter Director of Product Marketing, Weavix Yi Lin's expertise in navigating an incredibly competitive PMM job market was invaluable in my job search. Her feedback and advice is direct, but kind and was exactly what I needed to progress in interviews and truly differentiate myself amongst a sea of PMM talent. Additionally, the Courageous Careers community she has built is an amazing group of people who are eager and willing to share their time, insights, support, and connections to help one another. Working with Yi Lin was easily of the best decisions I have made and I highly recommend her to any PMM looking to take the next step in their career! Klarissa Djajalie Product Marketing Manager, UserCentric I was landing screening interviews but wasn't advancing so I joined Yi Lin's Program, and I am so glad I did! The program really helps you rethink your experience and work on your messaging and positioning for yourself, and the community is truly one of the most supportive and motivating communities of PMMs and aspiring PMMs out there. I've since landed an offer and I couldn't thank Yi Lin and the community enough for the support in the job search process and helping me find my confidence again. Khuslen Khosbayar Associate Product Marketing Manager, Kong Yi Lin's program has been an incredibly enriching experience for me. Though I initially entered the program hoping to land my next role (which I did!), I quickly realized that this program offered much more than just the promise of a new position , thanks to the carefully designed workshops, along with the active community she fostered. Going into my new role, I will keep in touch with the fantastic people I've met in the community! Thank you, Yi Lin, for fostering such a supportive and active community through your awesome program! Heather Ryan Director of Product Marketing, Workiva I was a multi-time founding PMM looking to transition out of startups and into a later-stage company. Four months after joining the PMM Job Search System, I landed an incredible IC Director role at a public company. Yi Lin’s program was a true turning point. I had already worked with several coaches, but none came close to the depth, clarity, and actionable guidance offered in the PMM Job Search System. It covers every step of the job search with a level of thoroughness that’s unmatched. The job market has changed, and so has the way we apply. If you’re looking for a clear roadmap to getting offers, growing within a supportive community, and making a meaningful leap in your PMM career, this is the real deal. I’ve already recommended it to several friends! Peggy Pan Head of Product Marketing, Uscreen Yi Lin helped me land a role in my dream field (even when the job market was so difficult). After my job search, I decided to continue working with Yi Lin in my new role to help me onboard. Because I value her insights, and also because I truly enjoy this meaningful coaching relationship with Yi Lin. See 70 more rave reviews on LinkedIn (Recommendations Section) Integrated and holistic I blend product marketing, strategy consulting, design thinking, and life coaching to support the whole person, not just the surface problem. Career challenges are rarely isolated, so I use an integrated, flexible toolkit to meet each client where they are. This approach comes from my own nonlinear path as an engineering consultant, marketer, founder, and coach. Real-world experience and results From B2B to B2C, PLG to sales-led, startups to global orgs, I’ve led, launched, and advised PMMs across it all. I’ve built teams, shaped positioning, and coached 200+ PMMs and leaders to thrive in their careers. I know it works because I have seen it work everywhere. Built for underdogs As an immigrant, career switcher, woman of color, and mom, I know what it’s like to lead without a map. I went from no PMM experience to Director in under three years , and now I help others do the same. Clients trust me not just for strategy, but because I get what it takes to rise up against odds. If you’re ready to turn uncertainty into results, for yourself or your team, I’d love to help. Learn More About Me What makes my approach different? Select places I've worked at: Reach your career goals with confidence and clarity. Book a Free Consult

Product marketing coaching to help you onboard, ace your first 90 days and grow as a new hire, with 1-1 coaching, masterclasses and access to a private community. Grow: 1-1 New Job Coaching Program Ace your new job with confidence, structure, and a clear path to success. The only dedicated PMM coaching program designed to help you master your first 90 days. Book a Free Consult See Program Details Taken and trusted by PMMs and PMM leaders at top companies such as: Starting a new Product Marketing role is exciting - but it can also feel overwhelming, as the actions you take (or don’t take) in your first 90 days - the most crucial period in a new role - will largely determine whether you succeed or fail. Does this sound familiar? ❌ “I know I’m capable, but I don’t want to seem clueless.” → You’re stepping into a role you haven’t done before and fear looking inexperienced or making mistakes. ❌ “I don’t want to burn out, I want to get this right.” → You want to deliver impact the right way, set yourself up for success, and be on the path to a promotion without overworking yourself. ❌ “I was laid off before, and I’m afraid of it happening again.” → You feel extra pressure to prove your worth quickly, leading to stress and burnout. Whether you are starting your first PMM role, stepping into leadership, transitioning into a new industry, or building from scratch as a founding PMM , you’re expected to ramp up quickly, prove your value, and drive impact - often without a clear roadmap . Here is the thing: without a structured approach, PMMs often spend months reacting instead of leading , struggle to gain influence, and risk getting stuck in execution mode. But there is a better way. The solution: a proven system to fast-track your success Grow is designed for the messy middle of your career, where you're stepping into a new environment, expected to deliver fast, and need clarity, credibility, and calm in equal measure. I created it because most PMMs are left to "figure it out", while also trying to look like they already know everything. As a career switcher turned PMM leader, I understand the challenges firsthand. Through years of hard-earned experience, I developed a proven system that enabled me to secure $250K+ in budget as a new hire, deliver Tier 1 projects within two months, and advance from a PMM newbie to Director in just three years. This same system has helped dozens of PMMs confidently navigate their first 90 days, establish credibility fast, and position themselves for long-term success. Together, we’ll ensure you have the right mindset, strategy, and tactical know-how to thrive in your new role from day one. What Clients Say About Working with Me Neal Patel Sr Product Marketing Manager, Nuvolo Working with Yi Lin has been one of the best decisions I have made for my career. Not only did she help me land a target role that I love, but she also helped me grow in my new role where she provided incredible product marketing advice. She simplifies complex PMM concepts such as GTM product launches by providing clear insights and frameworks to create a scenario where all stakeholders involved are aligned to hit key milestones. During my time working with her, I had many aha moments, and I've already started implementing her learnings and seeing the results. I would highly recommend going with Yi Lin to grow in your product marketer career. Thank you, Yi Lin! Emily Highstreet Head of Marketing, RevenueRoll "When I stepped into a Head of Marketing role at an early-stage startup, I was immediately tasked with owning positioning - something I knew was critical but didn’t have deep expertise in. I needed a thought partner to help me navigate this challenge, and a friend immediately pointed me to Yi Lin, calling her the best product marketer out there. From our first conversation, I knew I had found the right coach. Yi Lin was thoughtful, articulate, and introduced me to structured frameworks that helped me bring focus and clarity to the chaos of a fast-moving startup. Her guidance helped me bridge the product marketing knowledge gap, not just in execution but in building strategic cross-functional alignment. Working with Yi Lin has been like product marketing therapy - she’s not just an expert; she’s a true partner and support system. For anyone who is the only marketer in the organization or leading product marketing without a clear playbook, I can't recommend Yi Lin enough. Her coaching goes beyond instruction - she’s honest, supportive, and truly invested in your success. Peggy Pan Head of Product Marketing, Uscreen Yi Lin helped me land a role in my dream field (even when the job market was so difficult). After my job search, I decided to continue working with Yi Lin in my new role to help me onboard. Because I value her insights, and also because I truly enjoy this meaningful coaching relationship with Yi Lin. Terver Bendega Sr Product Marketing Manager, Tipalti When I transitioned into Product Marketing without direct PMM experience, I knew I needed help. I didn’t want to just ‘figure it out’ - a friend strongly recommended Yi Lin and knew she was the real deal , which is exactly what happened. Yi Lin gave me a clear, actionable roadmap that helped me quickly build relationships, ask the right questions, and impress my leadership team from day one . Even presenting my 90-day plan made a huge impact. She also helped me create a structured approach to launching products and managing cross-functional projects. After working with Yi Lin, within six months, I received an award from my company for my contributions - something I never expected so early on. And when it came time to advocate for my next step, Yi Lin gave me the courage and the exact strategies to advocate for growth and more responsibilities in my role. That’s why continuing to work with her was a no-brainer. I invested in myself once, and it paid off. Now I’m investing again because I know the ROI will be even bigger. Noelle Tomlin Product Marketing Manager, Lev As I began my new role as a solo PMM, Yi Lin's guidance was crucial during my onboarding process - she helped me structure my approach for immediate wins while also laying the groundwork for long-term strategic initiatives . I felt more confident and assured after working with her, as she has set me up for success! Principal Product Marketing Manager, High-growth B2B SaaS company Stepping into a Principal PMM role, I knew the importance of making a strong, immediate impact. I’ve followed Yi Lin’s work for a while, so it was a no brainer to partner with someone whose expertise and proven frameworks I trusted. In just our first session, she helped me cut through the noise and provided a structured approach to navigating my first 90 days with confidence and focus. I left that session with a strong sense of clarity and strategy for delivering impact. In finding Yi Lin, I feel like Scrooge McDuck diving into a gold mine of expertise and resources. I am excited to continue my journey with her and recommend her services to anyone looking for a trusted guide! Angie Ennamorato Product Marketing Manager, Deepki Going from a team of product marketers to a tech startup’s first dedicated PMM role was a big transition for me. I knew I needed help from someone who had done something similar to navigate my role successfully. Yi Lin brought in amazing qualities as a coach—perspective, wisdom, and empathy (to name a few)—that propelled me to a new phase of my career and job where I felt empowered to tackle opportunities and challenges. I would strongly recommend her to other product marketers who want to learn how to grow in their PMM careers, harnessing the value of their experience in a new environment. Kelly Parisi Sr Product Marketing Manager, Scorpion I had been following Yi Lin for some time, finding her content on LinkedIn so incredibly valuable, I can't believe how much amazing knowledge she gives away for free. That eventually led me to joining her program. I have learned so much from being part of her community for the past several months through my access to knowledge sharing from other PMMs, the relationships I've made along the way and of course, Yi Lin's expert guidance. She has helped me feel more confident and secure in my role as a PMM and I'd recommend her community and coaching services to anyone ready to level-up in their current role. I truly could never run out of good things to say about Yi Lin. Every PMM should be at minimum following her LinkedIn content regularly. Jordan Adler Product Marketing Manager, KickUp Yi Lin's program has been an incredibly enriching experience for me. With her coaching, I successfully launched my first product, built strong relationships across teams, and navigated challenges with confidence. More over, she is hands down my most trusted advisor , someone who genuinely cares about my success and goes above and beyond for her clients. She didn’t just help me build confidence- she helped me negotiate a huge pay increase, ensuring I was valued for my contributions. I highly recommend working with Yi lin in any stage of your career! Find More on LinkedIn (Recommendations Section) Exactly How It Works 2 Month 2: Build Strategy & Execute Now that you’ve secured some early wins, we’ll shift toward strategic execution. I’ll guide you through: ✅ Delivering high-impact PMM initiatives ✅ Strengthening your influence within your organization ✅ Advocating for yourself and navigating career growth conversations ✅ Executing effectively on key PMM responsibilities with confidence 3 Month 3: Drive Influence & Long-Term Impact With increased confidence and credibility, we’ll focus on long-term success by: ✅ Strengthening your strategic initiatives ✅ Learning how to showcase impact to leadership effectively ✅ Positioning yourself for sustained success beyond 90 days 1 Month 1: Gain Clarity & Quick Wins In our first month, we’ll focus on defining success in your role and setting you up for early momentum. Together, we'll: ✅ Develop your preboarding and 30-day plan ✅ Conduct a gap analysis to identify skill and knowledge gaps ✅ Pinpoint quick wins to establish credibility fast Flexible & tailored to your needs: While this framework provides a strong foundation, every engagement is customized. Our sessions will focus on what’s most pressing for you, ensuring you get personalized guidance based on your role, challenges, and career aspirations. By the end of 90 days, you will have: ✔️ A clear roadmap for long-term success in your role ✔️ Established credibility and influence with leadership ✔️ Built strong relationships across product, sales, and marketing ✔️ Avoided the common pitfalls that keep PMMs stuck in execution mode Terver Bendega Product Marketing Manager, Tipalti Yi Lin gave me a clear, actionable roadmap that helped me quickly build relationships, ask the right questions, and impress my leadership team from day one . Even presenting my 90-day plan made a huge impact. She also helped me create a structured approach to launching products and managing cross-functional projects. After working with Yi Lin, within six months, I received an award from my company for my contributions - something I never expected so early on. And when it came time to advocate for my next step, Yi Lin gave me the courage and the exact strategies to advocate for growth and more responsibilities in my role. Program Details & Pricing 6 hourly sessions over 4 months Unlimited email/messaging support between sessions Access to exclusive templates & guides Access to a private community with masterclasses, peers connections, and real time Q/A Investment $3,000 (payment plans available) Book a Free Consult FAQs Who are you and why should I trust you? Hi I’m Yi Lin! I’m a PMM leader and coach who has lived through the challenges you’re facing. You certainly don’t have to trust me, but here are the reasons why 200+ clients have chosen to work with me: I’ve been in your shoes. I started as a complete newbie to tech and product marketing and worked my way up to Director in just three years. I understand the imposter syndrome, the steep learning curve, and the pressure to deliver quickly in a new role, especially as a career switcher. I’ve been there, and I’ve built a proven system to help you succeed. Real-world expertise from an award-winning PMM leader. I’ve built and led three product marketing teams from scratch at startups and major tech companies (Autodesk, Teachable, and more). I don’t just teach theory - I help you think, communicate, and lead like a top PMM. A trusted industry voice. I’ve been recognized as a Top 5 PMM Coach by PMA, a Top 25 Marketing Voice by Exit 5, and have built a 27K+ LinkedIn audience over four years. My frameworks are widely used and shared by top PMMs. I understand the challenges of underrepresented professionals. As an immigrant and woman of color who came to the US along with nothing, I’ve faced challenges others haven’t - and I’m deeply committed to helping more professionals thrive, break barriers, and accelerate their careers. What makes this program different from others? This is the only PMM-specific onboarding coaching program designed to help you master your first 90 days. You get personalized coaching, hands-on frameworks, and industry-tested strategies. If you are not sure about my approach, please read this newsletter first: https://www.courageous-careers.com/30-60-90-day-playbook-for-product-marketers What if I have been in my role for more than 90 days If you’re still struggling with ramping up, stakeholder management, or proving your strategic value, this program can still help you course-correct and establish a stronger foundation. Or, perhaps the Thrive program might be better for you. I can help you decide which program is best on our intro call. What kind of group workshops can I expect? I host of variety of group workshops and networking events. These typically last around 1 hour and are geared around specific career growth and leadership topics. I’ve brought on experts from top tech companies like Clari, Square, and more. We host IRL events from time to time, mostly in NYC. Can you tell me more about your client community? When you start working with me, you’ll instantly gain access to my private Slack community of supportive product marketers and leaders. Our Slack is active daily with Q&A, referral opportunities, resources, memes, and more! You’ll be able to directly network with dozens of product marketing professionals who you can share your wins and challenges with. Ready to elevate your career? Schedule a Free Consult

Boo! 👻 It’s Yi Lin. Don’t worry, the only thing spooky in this newsletter is how fast AI is moving. Each month, I share practical insights on product marketing, career growth, and thriving in this changing landscape. And if you’re ready for more than what this newsletter can offer, you can always ​ explore my coaching programs and advisory services ​ . ​ This newsletter is sponsored by: UserEvidence Why customer proof matters more than ever In 2025, traditional case studies won’t cut it. Buyers want verifiable, AI-friendly proof tailored to their industry, size, and use case - not another static PDF. That means turning customer stories into proof that moves deals forward: blind-but-verified wins, bite-sized snippets your sales team can actually use, and competitive switch stories (e.g., “Why we switched from X to Y” ). UserEvidence’s new ​Evidence Gap 2025 report​  reveals what’s working (and what’s not) in customer proof, plus practical playbooks and tips you can steal today. 😉 → ​ Learn how to create customer proof that increases buyer confidence ​ Is AI making you sweat? You’ve been given an AI mandate. Maybe you are new to leadership. Maybe you’ve just stepped into a new role. Or maybe you’ve simply been handed the responsibility without much direction. Either way, the expectation is clear: “figure out how AI makes us more productive.” Translation: multiply yourself (and your team). The challenge is knowing where to start. While there’s no shortage of well-meaning AI tool lists, webinars, and prompts lists out there, they rarely cover what matters most: the strategy to design and implement a real product marketing-focused workflow . To see real results, you need clarity on your goals, a focused place to begin, and alignment with leadership. When I published the ​ State of AI in Product Marketing Report ​  a few months ago, I highlighted how PMMs are using AI. Since then, the biggest question I’ve heard is: “Okay, but how do you actually execute this in real life?” That’s what this issue is about: building real workflows, so you can use AI in a way that makes you more strategic, not just busier. And I’ve got a cool real-life example  at the end - so don’t scroll away too soon! Why AI adoptions fail Before we dive into how to build an AI flow the right way, it’s worth asking: why do so many attempts fail? An MIT study recently found that 95% of enterprise AI pilots never scale or deliver ROI ( ​source​ ) .  While that study focused on big enterprises, the same traps show up in startups and even small teams. Three themes kept coming up in my advising and coaching work: Unclear objectives → AI projects were launched just to “keep up,” with no defined problem or success metric. Lack of change management/guardrail → everyone experiments in isolation, but no one sets ownership, process, or guardrails. Skill gaps → teams jump in without expertise in the very workflows they are building, leading to shallow adoption or lower quality outputs. When you zoom out, you realize the problem isn’t a lack of enthusiasm; it’s the absence of structure. Most organizations (especially startups) treat AI as a quick productivity hack, not a business capability that deserves real design . How to build Product Marketing AI workflows the right way So what do the successful 5% do differently? They treat AI as a system, not a shortcut. For PMMs and team leads, that means resisting the hype, slowing down, and being intentional. Here’s how I advise my clients to do it: 1. Anchor to a business goal Start with strategy. Not “what can AI do?” but what does the business need right now? For example, if win rates are dropping because competitors keep undercutting you, your AI pilots should directly address bottom-of-funnel conversion. 2. Choose a focused use case Once the goal is clear, pick one workflow that maps directly to it. The mistake I see often is starting too broadly. “Product launch,” for example, isn’t a single use case; it’s five or six (research review, positioning, promo plan, enablement, content). No wonder teams get stuck. So how do you choose the right one? I keep two simple principles in mind: Small enough to solve, big enough to matter  (credit to Zapier). Start with more execution-focused tasks (left of the spectrum of the graphic below):  this is where AI has the biggest advantage. The temptation is to begin with things like positioning, the “big ticket” work. But those require the most human judgment (and a ton of stakeholder alignment). They are the easiest place for AI to fail. Start small on the left, prove value, then expand. 👉 Example: if competitive intel is the challenge, begin with an AI-assisted workflow that aggregates competitor updates for a single top competitor. Document the process, capture the win, and build from there. Don’t get hung up on the format. It doesn’t matter whether that first use case is just a few saved prompts, a lightweight custom GPT, or eventually an agent (yes, agents are cool, but no, you absolutely don’t need one from the beginning). What matters is that it’s tied to your business goal and scoped small enough to deliver a win. 3. Define what “good” looks like Before writing a single prompt, map the structure of a high-quality output. For instance, if you are creating a competitive landing page, define the essential elements first: headline, proof point, differentiator, and CTA. Don’t rely on the tool you’re using to shape what good looks like. Feed it the right inputs: battlecards, customer stories, landing page examples, brand guidelines. That’s when AI starts to feel like an extension of the team instead of random internet text or AI slop. 4. Build in public, share, and iterate As you are building your workflow, document wins, refine prompts, and expand step by step. One client started with AI call summaries, then layered in objection handling, and only later tackled messaging. Each stage built credibility and confidence. Despite any “expert advice” you see, the fact is: AI is new for everyone. No one has the playbook figured out. The PMMs and team who win are the ones who share what they are building. Post your workflows, host a quick demo at all-hands, or create a shared prompt library. This not only builds momentum but positions you as the AI champion in your org. Pro tip:  bake your process into the workflow itself. Include usage notes, dos and don’ts, and review loops so the system is as much about guidelines as it is about outputs. Case study: The landing page that built itself (almost) To bring this process to life, let me share a real example from a founding PMM client (with his permission, of course). His small team was spending weeks writing and re-writing landing pages, with unclear ownership and inconsistent quality. So he built an AI flow that blended automation with human strategy, which results in not just faster output, but better output. The project at hand was a product landing page positioned against a major competitor (a legacy system), tailored for a specific persona. It wasn’t about creating new positioning or messaging (that work was already done, and remember, that’s a “right side of the spectrum” task). The challenge was translating existing messaging into landing page copy using a repeatable, proven framework. I helped him think through the backend strategy that made this workflow scalable. Here’s how we broke it down (which roughly mirrors the steps above). It all comes back to what I said at the beginning: start with strategy. 1. Anchor to a business goal Before writing a single prompt, we clarified the business outcome. The team’s priority was improving middle-of-funnel conversion, getting more prospects to book demos. 2. Scope the right use case From there, we explored different ideas. After discussing a few, we landed on the use case of building high-converting competitive landing pages. This is because expanding to all  webpages would have diluted the model and produced inconsistent outputs. Competitive landing pages, on the other hand, were: Directly tied to demo bookings → a measurable outcome the business cared about. Straightforward → easy to define what “good” looked like. Self-contained → mostly owned by marketing, which reduced dependencies and made it faster to implement. By starting here, we set the project up for a fast, credible win that built confidence and momentum. 3. Research, codify, and feed the tool with best practices. Rather than relying on guesswork, my client and I pulled from industry frameworks, my own experience advising PMM teams, and examples of top-performing landing pages. He then fed these, along with other critical information, to Claude. It included artifacts like: Product and positioning guides Competitive battlecards Strategy frameworks Success stories and customer-voice databases Style and messaging guidelines And that’s the great news: odds are, you have all of this (and more!) already. Each of these assets taught the AI how the brand thinks, writes, and differentiates. This is what made it more than a generic content generator and instead an extension of the team’s expertise. 4. Layer in collaboration, guardrails, and share From there, the workflow was built with guardrails: it asked clarifying questions before generating anything, cited sources for every claim, and routed outputs through review loops. This way, you are not just generating good output but modeling the right review process and workflow. For example, here’s a screenshot of an automated Slack message created using an MCP connector (a new open standard that lets AI connect securely to tools like Slack, Notion, or Google Drive). Whenever someone on the marketing team publishes a new page, the system instantly notifies the PMM and routes it for review. So, how does the workflow look in action? From the user side, it’s NOT just a one-and-done prompt. The system is built with guided steps  that prompt the user for additional information, e.g. different styles of messaging for the headline from a pre-set number of options. And then comes the “wow” moment: the tool pulls it all together into a full landing page draft, complete with sections, copy, and even a lightweight HTML mock-up. What used to take days of back-and-forth now takes minutes, and the quality is anchored in the team’s own strategy and assets. Here are some anonymized screens of the V1 landing page below, with all sensitive information removed. Of course, with more iterations, it will get better and more specific, but this was a significant improvement over what was there before. Voila! And it’s done. What once took days now takes a few minutes, producing sharper, better-aligned content. More importantly, my client walked away with a repeatable AI flow that can scale across the team. Here’s what I want you to take away: AI only works when paired with a strong strategy.  Start with a business goal, choose one low-risk workflow, and prove the value, then expand. The tools don’t matter as much as the process.  ChatGPT, Claude, Gemini, or purpose-built tools, they all work. What matters is how you design around them. What’s next? Over the past year, I’ve worked with PMMs and leaders at fast-growing startups to design AI flows that don’t just save time but also strengthen strategy. Of course, you can absolutely experiment on your own. But many of my clients chose to work with me because they want to accelerate what they are already good at, with a trusted partner who helps them dig deeper, refine their thinking, and explore bold ideas with confidence. Together, we turn workflows into strategies that win executive buy-in, and that’s what helps them lead with greater clarity, influence, and impact. 👉 If you’d like to explore how ​coaching​  can transform your career,  simply contact me here. I’d love to help you build your next strategic flow so you become a truly AI-empowered product marketer and leader. :) See you next time, Yi Lin

You’re not imagining it,  landing a product marketing role really is  harder than ever. A few years ago, tech was fueled by “growth at all costs.” Companies rushed to hire and were willing to bet on potential. Today, the pendulum has swung the other way:  Open tech roles have been cut nearly in half since 2022  Salaries are down 10–15% on average (source: clients and PMA)  Each posting now draws 5–10x more applicants Plus, job descriptions are vague, with PMMs asked to cover far more than their scope. And once you do  land a role, the expectation is to deliver impact fast, with less ramp time and fewer resources.  The good news is that even in this tough market, more companies are waking up to the value of product marketing. But most are still chasing a “unicorn” PMM: someone who can do it all, which makes it even more critical to stand out in the right way. That’s where I’ve spent the last four years focused: helping PMMs land roles faster. More than 300 people have used my PMM Job System to break through , and in just the last 6 months, 35 clients have gone from long, stalled searches to offers in hand. Before you read on, enrollment for the PMM Job Search System now runs in application windows  just a few times a year. The final 2025 window is open now. Once it closes, you’ll need to wait until January to join. Alumni cut their search time from months to weeks, joining companies like AWS, Walmart Connect, DoorDash, HubSpot, and fast-growing AI-native startups. The program is better than ever , with new resources to help you stand out faster:  ✨ AI Interview Co-Pilot  – built from real coaching insights  ✨ Portfolio-Building Module  – showcase impact and prove value fast  ✨ Workshop Recordings Library  – access replays + notes 👉 Apply now before enrollment closes on Oct 3  In this newsletter, I’m sharing 6 of the exact strategies I coach clients on ,  the ones that are working right now  to help PMMs cut through the noise, stand out in interviews, and land jobs faster in today’s market. Let’s dive in. Six things to do differently to land your PMM job today Achieve PMF when the product is you If your strategy has been “apply to everything and hope something sticks,” you already know it’s not working. Not in this market. You need a smarter, more targeted approach, starting with getting crystal clear on the kinds of companies you’re going to target. If your approach now is the left side of this visual, it’s time to start moving towards the right side. If you follow me on LinkedIn, you’ve heard me say this before. But it’s more important now than ever: just like you’d build an ICP for a product, you need to build your ideal company profile . Think of it like product-market fit, but this time you’re the product. It’s all about finding the intersection of your strengths, passions, skills, and values with the roles and companies that truly need what you bring to the table. Adopt a multi-pronged approach to finding jobs  If cold applying to jobs ever worked, it certainly doesn’t anymore. You may get a sense of satisfaction after clicking that “EasyApply” or “submit” button, but odds are it’s getting you nowhere fast. Today’s job search is very much about quality over quantity. Consider the following stats when it comes to cold applying vs. getting a referral: Merely landing an interview is a challenge with cold applications, with only 2-5%  leading to an initial discussion. Compare that to a referral that leads to roughly 40% of  referred candidates getting interviewed (nearly 10–20x better odds.) The story is similar to job offers: while just 0.1–2% of cold applicants get hired , about 16% of referred candidates  who interview receive offers. (Sources 1 , 2 , and 3 )  In short, you need more than a resume and cover letter to get your foot in the door these days. You need a connection, and there are a few ways to navigate this – via cold outreach or tapping into your network.  For cold outreach, LinkedIn is your best friend. It’s a fairly simple process: Give it a few days before following up, and be sure to apply online as well.  Step 4 is where most people get stuck: what do you actually say ? My program offers a deep dive  into writing outreach messages that get responses  with multiple scripts. As you can see from the message below, these guidelines help job seekers get a response in record time (sometimes - within minutes!)      Networking (people love to hate it, but you need it) You’ve heard it before because it’s true: don’t wait until you’re job searching to start networking.  The strongest opportunities often come through the hidden job market, with roles shared in communities or directly by hiring managers before they ever hit LinkedIn.  In my PMM community alone, members regularly share openings early; they’re posted widely, giving my clients a leg up that’s led to real interviews and offers.  I’ve seen it time and again: clients land jobs not just through applications, but through the relationships they’ve built and nurtured over time. One client of mine landed two offers  through referrals from relationships she had kept warm, proof that applications alone aren’t enough. Keeping connections “warm” is so critical, and it should feel natural. A quick check-in, a genuine comment, or sharing something useful can be the difference between hearing about an opening early or missing it altogether.  Doing portfolios the right way  Let’s be clear: portfolios can help you stand out, by only if you do them right. Too many PMMs waste time on pretty-looking collections of assets that don’t actually tell a story or show impact. That kind of focus on style over substance can hurt more than it helps.  Instead, think of your portfolio as a way to differentiate. In my program, I walk through 4 different formats – from simple work samples to tailored, role-specific projects – that showcase your skills the right way, using the following principles: Timing matters : Portfolios are most effective once you’re in the interview process, when you know what the company actually needs. Less is more : Pick 3–5 projects that align with your positioning and level, and structure them as short case studies (context, role, approach, results). Go beyond “pretty” : Your goal isn’t to wow with design, but to make it easy for a hiring manager to see your thinking, execution, and impact. This means including projects that are aligned with your level, and how both internal strategic documents and external assets. Differentiate with value-added work : For dream roles, consider creating a tailored project after an interview—something that directly solves a challenge the team raised. Done right, these can turn you from “good candidate” into the obvious  choice. I dive into specific examples and how to build, organize, and present them, but here is a simple layout that has worked for many clients. Of course, the devil is in the details. So you’ve landed the interview. What now?! Preparation is your Superpower Everyone gets nervous before interviews – I’ve yet to meet someone who doesn’t! The nerves usually come from feeling like you’re not in control. That’s why I focus so much on preparation with my clients: it puts you  back in the driver’s seat. Deep breathing and pep talks are fine, but nothing beats being relentlessly prepared . Acing interviews is 80% prep . That’s why I built my 7-step interview process that covers everything from researching the company, to crafting your “why me” story, to practicing smart, differentiated answers that set you apart. With a clear structure, you stop guessing and start showing up with confidence. Unsurprisingly, AI tools like ChatGPT have become popular for practice. They’re fine, but let’s be real: the answers often sound canned and make you blend in, not stand out. So I created my own AI Interview Copilot , built directly from hundreds of real coaching sessions and client interactions. It takes you through my 7 steps, critiques your responses, and helps you practice until you sound sharp.  Beta testers in the program told me, “Yi Lin, it’s like having you sitting in my head during prep sessions.”  Which I’ll take as a compliment! ;)    Prepping your answers: PSAR vs STAR You’ve likely heard of the STAR method for answering interview questions: Situation, Task, Action, Results. While this can work in some situations, it’s less than ideal for product marketers. For one thing, the “situation” and “task” pieces tend to take too long to describe, and can usually be combined. For another, and most critical,  it ignores the most crucial piece for PMMs: the process . That’s why I’ve developed my own framework for answering interview questions, curated for product marketers: PSAR.  Let’s take a look at how this works, and what it might sound like in a real-life scenario for a question that lots of PMMs get and struggle with in interviews:  “What metrics do you use to measure the impact of product marketing?” Step and explanation Real life example Process: Start by walking through the process which helps show systems-level thinking and makes it easier to follow along.  “Lots of people think about attribution, but I prefer to measure my success based on contribution. I start with the business goal, then figure out where the biggest focus in the funnel is. From there, I determine which upstream marketing metrics I can influence, and then create that contribution story.” Situation: This combines the task, situation, challenge , project, goal, etc – which should be a short and concise statement. “At my last company, revenue was the top priority. When I dug deeper, it became clear that pipeline creation (middle of funnel) was the real bottleneck. My job was to show how PMM could help fill that gap.” Action: This is where you dive in to provide detail of how exactly you did it, by following the process you laid out earlier. Call out specific steps (1, 2, 3, or who, what, when), and a specific, memorable insight to show the WHY.  “I partnered with Demand Gen on a tier-one launch focused on new AI capabilities, which I knew would bring in a lot of pipeline. We developed a highly innovative strategy centered on influencer activation. I then built messaging and assets for high-priority segments, as well as enablement for Sales and all our influencers.  To measure my impact, I tracked: Content engagement (deck usage, webinar attendance) Sales and influencer feedback on assets And other channel metrics And, I regularly shared updates on how this work supported pipeline goals.” Results: End with showing the impact and the result you generated, and any learnings .  “The launch drove a 25% increase in marketing-sourced pipeline that quarter. Sales adoption of my assets was 80%+, and AEs called them out in all-hands as helping accelerate deals. The influencers gave me shoutouts in our Slack channel for having delivered a comprehensive prep doc. Beyond the numbers, I built a repeatable way to connect PMM contributions back to business outcomes.” You can clearly see from the example how this framework helps you stand out amongst candidates due to the focus on process, action, and results .  Of course, nailing the answer framework is just one part. Ensuring you’re able to give those answers with confidence in the throes of an interview is what makes the difference - and this is where practice comes in.  You can take pages of notes and memorize your answers, but until you say the words out loud, again and again, you haven’t really nailed them .  That’s the difference between knowing what you want to say and being able to deliver it confidently in the moment, and it’s why practice is a cornerstone of my PMM Job Search System. Clients don’t just prepare alone; they sharpen their skills in multiple ways: Practicing with accountability buddies Getting feedback in live group workshops Rehearsing with my AI interview copilot This mix builds muscle memory and confidence, so when the real interview comes, you’re not scrambling; you’re ready. Now, let’s talk about what you can do once the interview is over to really leave your mark on the interviewer’s mind.  Going above and beyond  This market is brutally competitive, which means what worked before won’t cut it now. To stand out, you’ll often need to go further than you might have in past searches. Take-home assignments are a hot topic; sometimes they’re useful, sometimes they’re just free consulting. Protect your time, but for the right roles, think of them differently: they’re not just a test of you , they’re your chance to test-drive  the job and see if it’s really a fit.  In my program, I break down how to tackle assignments strategically. And even if you’re not given one, you can still stand out by sharing something that shows how you’d hit the ground running from day one.  For example, my clients have done the following: Submit a 30/60/90 day plan  (using my framework/template ) to outline how you’d create impact from day one. Share a short customer video recording  that captures real voice-of-customer insights and shows how you think about messaging. Mock up an “AI vibe-coded” tool  like a quick landing page prototype to demonstrate creativity and execution. Proactive efforts like these make it easy for the hiring manager to picture you already in the role.  Bonus: 3 success stories from real job seekers  So now you have learned all the important tips, you might be wondering how this actually works in practice. So I am going to share with you three stories of successful job seekers who used the above approaches to land jobs in this insane market.  They include:  A founding PMM at an AI-Native startup - Raniz Bordoloi  A Sr PMM in a scale-up  - Brandon Hatter  A PMM at a large enterprise - Robin Yee  Case Study 1: How Raniz pivoted to an AI-native startup and landed a Head of PMM role  Before: Starting point  Raniz is an amazing PMM who was working at a larger company but felt stagnant due to the entrepreneurial energy he craved. He wanted to pivot into a high-growth, AI-native startup, but was not sure how to navigate the job search. His narrative needed to reflect recent AI work and his builder mindset, and his search approach needed clearer focus. Breakthrough: What changed with the PMM Job Search System  Through the program, Raniz refined his strategy and execution: Defined a target list → Focused on AI-native, investor-backed startups with clear product–market momentum and a path to broader marketing ownership. Built a sharp narrative → We connected his experience launching AI-related products and his early SDR and entrepreneurial background into a “founder-like PMM” story that resonated with startups. Upgraded interview delivery → He practiced structured, consultative answers that showed judgment and impact. Focused his efforts → Instead of chasing everything, he learned to say no to roles that didn’t align, especially ones asking for excessive take-home assignments. This clarity and focus gave him the momentum he was missing. Results: The transformation In two months, Raniz moved from broad exploration to a tightly managed pipeline. He progressed through ~70 interviews across 20+ active processes, earned two offers , and accepted a founding PMM role at a coveted AI-native startup, backed by top-tier Silicon Valley venture capital firms. Takeaways: What you can learn Positioning is everything → Reframe your background to align with the market you want to enter. Quality > quantity → Saying no to misaligned opportunities saves time and energy. Prioritization compounds → Weekly goals and pipeline reviews keep execution aligned to outcomes. Momentum builds belief → Each interview helps reduce imposter syndrome and sharpen your story. Stats at a glance ~30 applications submitted ~70 interviews total 20+ active interview processes at once 2 offers in 2 months Start date: August 2025 Accepted role: Head of Product Marketing at AI-native startup Case Study 2: How Brandon turned a layoff into a better role in just 4 weeks Before: Where he was stuck Brandon is an experienced and talented PMM who was laid off in July 2025 as part of a reduction-in-force. While he knew the company wasn’t the ideal fit for him long term, he was still facing a tough market. Outside his domain, his applications were getting historically low response rates, and he worried about how competitive the job pool had become. Breakthrough: What changed with the PMM Job Search System  By doubling down on the system of focusing on where you have specific advantages, Brandon refined his strategy: Targeted the right niche → Instead of chasing broad roles, he leaned into his IoT/industrial SaaS expertise. Personalized outreach → Using my LinkedIn message template, he reached out directly to the VP of Marketing after applying, sparking a recruiter response in just 3 minutes. Streamlined storytelling → Each step of the process (recruiter call, VP call, panel, GTM presentation) built on his strengths and positioned him as the obvious fit. Results: The transformation Within 4 weeks of searching, Brandon went from a layoff to a new opportunity. He joined AssetWatch as a Senior PMM at a larger, later-stage company with ~300 employees, a recent $75M Series C, and an environment more in line with his working style and career objectives. He landed the offer after just 3 weeks from application to acceptance. Takeaways: What you can learn Focus where you have an edge, domain expertise can massively increase your response rate. Direct, targeted outreach beats cold applications (his recruiter responded in 3 minutes!). Every touchpoint in the process is a chance to reinforce your fit. Layoffs can be a launchpad, if you position yourself correctly, you can bounce back stronger. Stats at a glance: Laid off July 15 Application sent July 31 Recruiter responded in 3 minutes to LinkedIn outreach Offer made Aug 19 (3 weeks from app → offer) ~50%+ response rate within IoT/industrial SaaS niche Sr. PMM offer accepted at AssetWatch Case study 3: How Robin landed a PMM role without “traditional” experience Before: Where she was stuck Robin is a smart, driven PMM with a unique background that includes building a successful small business. But what made her resourceful and adaptable also became a challenge in the job market, employers struggled to see how her experience translated into product marketing at a larger company. After nearly 200 applications and 17 interviews, she kept stalling out at the hiring manager stage. She began to wonder if her background would ever be “enough” to compete. Breakthrough: What changed with the PMM Job Search System  Instead of trying to brute-force her way into a role, Robin worked with me to refine her approach: Positioning her background → We reframed her experience across both entrepreneurship and traditional large enterprises as evidence of her scrappiness, adaptability, and ability to thrive in fast-moving and complex environments. Targeting the right companies → She stopped applying everywhere and focused on companies open to nontraditional talent (and said no to those in industries that required too much domain expertise). Sharpening her story → Through mock interviews, she practiced connecting her skills to PMM language and telling her story with confidence. Iterating her applications → Each application became more targeted, each interview a chance to improve. Results: The transformation Within three months, Robin’s search flipped. She went from rejection after rejection to 64 interviews across 32 companies, sometimes juggling 11 at once. By March 2025, she had secured a PMM role at a company that merged with Thomson Reuters, a globally recognized enterprise, proving that even without a “classic” background, her skills and story were enough. Takeaways: What you can learn You don’t need a big-name company on your résumé or a straight line career story. What matters is how you tell your story. Learn the language of PMM to connect your experience to what hiring managers expect.Target the right companies instead of spreading yourself thin. Every interview is practice; treat it like a conversation and keep iterating until you land your yes. Stats at a glance Before After the PMM Job System  200+ applications before coaching 17 interviews with no offers (stuck at HM stage) 64 interviews at 32 companies after coaching 11 interviews simultaneously during peak momentum 1 offer landed within 3 months Start date: March 2025  Accepted role: Product Marketing Manager at Thomson Reuters  Let’s get you hired.  It’s absolutely possible to job search on your own. Many PMMs do. But the reason more than 300 PMMs have chosen this system is because it makes the process faster, less overwhelming, and more effective. Plus, you don’t have to do it alone. 🚀 Applications for the Job Search System's Q4 enrollment window close October 3. Once you’re in, you’ll get immediate access to the full system and can start right away. It’s 100% risk-free : do the work, and if you’re not satisfied, I’ll refund you in full within 30 days.  If you’d like to understand exactly how PMMs have benefited from the system, please read 80+ verified client reviews on my LinkedIn profile recommendations , stories of PMMs who went from stalled searches to multiple offers. Don’t spend another quarter wondering if things will change. Apply now to secure your spot and start 2026 in the role you deserve. You’ve got this!

This newsletter is brought to you by two tools every PMM team should have in their toolkit: GetWhys – Do instant customer and prospect research that fuels strategic insights (with real humans and not just AI). Book a demo with the founder   and discover what they already know about your prospects! Navattic – Create interactive demos for the entire GTM workflow that wow customers and empower sales. Create a demo for free in seconds and start driving adoption today. Why being a manager is so hard:  It’s your first day as a new PMM manager. Slack is blowing up. Sales wants new battlecards. Product wants launch positioning. AI is spitting out draft messaging faster than you can review, and your team is staring at you for direction. AI was supposed to make things easier. In some ways, it has: productivity gains are real. But the tradeoff is more noise, lower motivation, and less perceived control. Instead of freeing you, AI has created even more for you to filter, refine, and lead. Meanwhile, executives are chasing AI strategies faster than managers can wrap their heads around them. The gap between their expectations (“Ship more, faster!”) and your reality (“We’re still figuring this out”) keeps widening. These are the exact moments where most new managers stall out , spinning in uncertainty, second-guessing themselves, and wasting precious time on tasks that create less impact. The result is lower team momentum, less visibility with leadership, and more personal burnout. Here’s the good news: no one is born a great manager.  It’s a skill you can learn, and in the age of AI, it’s one of the most important ones. Because while AI can crank out content, it can’t lead people. That’s your job, and it’s the part that matters most. The true job of a manager  In all the noise, it’s easy to forget what managers are actually  for: To maximize the long-term output and growth of the team in service of the business. People lean on that Spiderman quote all the time, because it’s true: with great power comes great responsibility.  The core of management is serving others, NOT wielding power over them. Managers who are primarily looking out for themselves will quickly fail (or be hated) because they are simply playing politics badly. They may succeed for a time, but their reputation won’t carry them far, because their goals are misaligned with what true leadership calls for .  For PMM managers, being successful requires 4 key foundations:  Purpose : Defining the narrative, priorities, and what “good” looks like for all the areas of responsibility when it comes to your role.  People : Coaching, setting standards, giving feedback, and helping each PMM do their best work. Process : Installing cadences and systems so great work ships on time and with quality. Performance : Determining how the team is measured, held accountable, and, importantly, celebrated and rewarded.  In an AI-heavy world, the “Process” lever matters more than ever. Without it, you just get faster chaos. How people become managers (and why it matters) So, how do you thrive as a new PMM manager? Before we dive in, let’s look at the main ways people become PMM managers. You’re probably finding yourself in one of the scenarios below, so keep that in mind as you continue reading. But one thing is for sure: whatever situation you’re in, you’re figuring it out as you go along.  I’ve been through all three scenarios myself and coached dozens of PMMs through them, and I know how disorienting they can feel without a roadmap. Here are the three ways you become managers: You were promoted internally.  Advantage: You already have social capital and have little learning curve Risk: hard to reset expectations with peers-turned-directs You were a founding PMM.  Advantage: You also have social capital and no learning curve  Risk: lack of role clarity, no one above you to guide you in terms of product marketing You were an external hire.  Advantage: You have a clean slate/fresh start  Risk: zero context, high scrutiny… and longer learning curve  Since we can’t cover every challenge you’ll face in a single newsletter, we’re going to cover the most tactical situation: your first 90 days (who doesn’t like a 90-day playbook?  😉 ) . This is a critical time that will make or break your success in this role and at this company. Messing this up is extremely hard to come back from.  But you’re not going to mess it up! You’re going to follow the plan I outline below, and absolutely crush it. This plan works whether you’ve inherited the team or built it from scratch,  and it’s designed for the messy reality of PMM (multiple stakeholders, ambiguous priorities, and the occasional low performer). So let’s get started.  The 30-60-90 Day Plan to Thrive as a New PMM Manager We’re going to look at each 30 days through a three-pronged lens: Personally  = how you measure, set up, and manage your own PMM leadership “system.” For your team  = what you put in place to grow, support, and structure the people. Cross-functionally  = how you align outwardly. A note before we dive in: as a new manager, your company has made a big bet on you. For the first few weeks, it’s natural to consume value such as asking questions, drawing context, and leaning on others. But quickly, you must flip the balance and start producing value: delivering clarity, quick wins, and outcomes that prove the investment was right. That shift is the essence of this 30-60-90. If you want help tailoring this playbook to your own messy reality, that’s exactly what I do with clients inside my coaching program .  Days 0-30 Goal:  Gain clarity, build trust and start shaping what “good” looks like. Your first month as a PMM manager isn’t about rushing in with fixes. It’s about listening deeply, absorbing context, and laying the foundation for how your team will operate. Personally : Spend this time getting clear on the company’s strategy, KPIs, and GTM processes. Audit the assets and systems you inherit such as messaging docs, GTM plans, enablement materials, so you can see both the quality of past work and the current gaps. Start sketching a lightweight “Definition of Done” for deliverables (what makes a messaging doc or launch plan ready), but wait to finalize until you’ve invited your team’s input. For your team:  Build trust through 1:1s with every direct report. Ask about their goals, challenges, and preferred working styles. Begin to establish the right rhythms like standups, 1:1s, launch reviews, but resist the urge to overload the calendar. Make it clear your job is to help them succeed, not just enforce rules. Cross-functionally:  Schedule intro conversations with Product, Sales, CS, and Demand Gen leaders. Ask what their biggest pain points are with go-to-market today and where PMM could add value quickly. Look for one or two easy wins you can deliver in partnership, ideally small moves that prove PMM’s value without derailing your listening tour. Key Deliverable:  Business, team and stakeholder assessment summary Questions to ask in stakeholder conversations One of PMM’s superpowers is cross-functional collaboration, and these early stakeholder conversations are your chance to uncover how things really  work.  5 questions to ask: Of course, the information you uncover will only be as good as the questions you ask. Ask each of your “interviewees” the following questions to get to the heart of what matters to them: What are your top priorities right now?  (Reveals how they’re measured and what matters most in their world.) What’s your biggest challenge, or one thing you wish worked better in go-to-market today?  (Surfaces pain points and opportunities for quick wins.) When you think about the customer we serve best, who comes to mind?  (Checks alignment on ICP while drawing out real examples.) What does a great partnership with product marketing look like to you?  (Clarifies expectations, builds trust, and positions PMM as a collaborator, not an order-taker.) What do you enjoy most about working here?  (Uncovers cultural strengths and helps you see what keeps people motivated. Example: A new PMM leader at a Series C SaaS company I worked with identified a troubling insight from her sales counterparts. She found the Sales team frustrated that every rep told a different story in the pitch deck. Instead of jumping into a full messaging overhaul, she partnered with a few AEs to identify three “must-say” value points. Within a week, she circulated a one-pager with those points for reps to test. It solved a real pain quickly, earned credibility, and bought her the trust to lead a larger messaging refresh later. Days 31–60 Goal:  Diagnose and tune the PMM operating system. By month two, you need to start shifting from value consumed  to value produced . With trust established, this is the moment to shape rhythms, tools, and expectations that make PMM’s impact visible. Personally:  Move from absorbing context to refining systems. Introduce lightweight tools or rituals that elevate quality, like a standardized launch brief for Tier 2–3 launches. Define success by aligning on PMM KPIs tied to business impact (win rate, adoption, pipeline contribution) while also clarifying process metrics you directly control. And don’t just delegate everything , keep one or two complex projects on your plate (e.g., pricing, segmentation, narrative) to model excellence and demonstrate your individual value. For your team:  Establish a clear mission statement and success metrics for PMM that connect back to company goals. Refine your operating rhythm, such as meeting cadences, planning cycles, and review structures,  so everyone knows how work will flow. Decide what to tackle now vs. what waits until next quarter. Run a skills gap assessment for individual team members and start investing in development. Begin setting expectations for performance, but keep the emphasis on coaching and support. Cross-functionally:  Share your draft operating plan with Product, Sales, CS, and Marketing leaders. Frame it as a collaborative roadmap that reflects what you heard in your first 30 days, so partners feel invested and excited about where PMM is headed. This alignment builds credibility and smooths execution. Focus on getting 80% of the result with 20% of the effort , quick systems that solve most of the pain without creating bureaucracy. Key Deliverable:  Draft team operating plan  Example:  When I joined Teachable as Director of PMM, there wasn’t a real function in place. My small team had little PMM experience, and launches were happening reactively with no framework. What I didn’t  do was roll out a massive, theoretical process that would take months to implement. Instead, in my second month, I piloted a lightweight GTM brief (who, why, what, how, when) with a PM on a Tier 2 launch, paired with my messaging canvas. The launch went smoothly, the PM had a lightbulb moment on the value of PMM, and the simple framework quickly became the model for future rollouts. This is an example of an 80/20 fix that delivered impact fast.  Days 61-90 Goal:  Deliver visible wins and cement PMM’s culture. By the end of 90 days, you need to prove momentum and impact. Too many new leaders think they can “just learn” for three months, only to find their managers frustrated, and in today’s economy, I’ve seen people let go before they even found their footing. While I don’t want to scare you, I do want to make it clear that in today’s environment, you can’t afford to wait.  Most managers I work with admit this is the hardest part, but once they practice it with support, it gets easier, and they can provide results faster. Personally:  Step fully into leadership by shipping 1–2 visible outcomes tied directly to business impact — a refreshed product narrative, an adoption campaign, a competitive win-rate improvement. Track results with a simple scorecard so the org can see PMM’s contribution. Keep one high-complexity project on your plate — it reinforces your value and sets the bar for the team. For your team:  Delegate ownership of key PMM domains (competitive intel, research, enablement), giving each person space to lead. Cement culture by celebrating smart decisions, creating a “stop doing” list to cut unproductive habits, and modeling the behaviors you expect. If performance issues persist, clarify next steps with HR, while also identifying future hiring needs. Cross-functionally:  Elevate your partnerships by sharing both results and what’s next with senior leadership. Host a Q1 outcomes review and preview your strategic priorities for the next few quarters. Introduce a PMM charter that defines what the team owns, supports, and doesn’t cover. This positions you not just as a new manager, but as a trusted partner shaping the company’s growth story. Key Deliverables:  Refined 90-day team strategy  Example:   By month three, one new PMM leader who had inherited a misaligned team knew it was time to show impact. After spending her first 60 days listening and aligning, she moved decisively into action. She reset the company’s launch cadence so teams weren’t shipping randomly. She introduced a messaging workshop that raised the bar for quality across functions and made tough but necessary calls on team structure. These visible moves not only delivered immediate wins but also signaled a cultural shift. An important note on giving critical feedback With the 90-day plan, you should have a clear blueprint to go from overwhelm to confidence and thrive as a PMM manager. But there is one mistake I see so many new managers make that is worth calling out.  When you step into management, it feels natural to want your team to think of you as approachable, supportive, even “the best boss they’ve ever had.” This can be especially difficult if you’ve been promoted internally and have gone from being a peer to a manager of your former PMM team members. But the danger is this: when being liked takes priority, you avoid the very conversations that make you effective. And that avoidance doesn’t just impact one person. It quietly shapes your whole culture. If unhelpful or toxic behavior goes unchecked, people assume it’s tolerated. Over time, that erodes trust and performance across the board. Your job is to build a team that respects you, trusts you, and performs at its best. And that requires giving clear, direct feedback, even when it feels uncomfortable. Most of us never learn how to do this! But the process below will help guide you. If you do this well, your team WILL probably end up liking you. But that should be the byproduct, never the main goal. A research-backed framework for feedback Management literature has studied this problem for decades, and several frameworks converge on the same idea: feedback should balance care with candor. Taken together, these insights can be distilled into a six-step feedback flow . Here’s how this might play out in practice.  Example: Imagine you notice someone taking credit for a teammate’s work. In your next 1:1, you might say: Observe behavior (be specific + timely) :   “In yesterday’s meeting, I noticed you presented XYZ as your work.” Ask with curiosity before judging intent :  “It seemed like there was overlap with [colleague’s] contribution. Can you walk me through how you saw it?” Name the impact on others :  “When credit isn’t clear, it can create confusion and make others feel undervalued.” Connect to shared goals and values :   “Our team succeeds when we collaborate openly and recognize each other’s contributions.” Invite ownership for next steps :   “How can you make sure credit is clear in future meetings?” Reaffirm support:   “I’m raising this because I want you to succeed here, and part of that is building trust and influence on the team.” Done consistently, this builds a culture where expectations are clear, feedback is normalized, and respect, not likeability, becomes the foundation of your leadership. Conclusion: your journey from contributor to multiplier The transition from individual contributor to people manager is one of the most significant career shifts you’ll make. You’ve already proven you can do the work yourself; now the real test is whether you can make others better by setting standards, building trust, and creating systems so the team can deliver without your hand in every detail. Of course, this requires unlearning old habits, building new skills, and changing how you measure success. And it’s not something you can figure out by reading articles or asking AI for advice. That’s why so many new managers feel stuck: second-guessing decisions, spinning in uncertainty, and wasting time on less impactful work. Here’s what my New Job Coaching Program  gives you: Structure  – Proven frameworks, roadmaps, and accountability that take the guesswork out of your first 90 days and beyond. Solutions  – Tailored advice on how to apply those frameworks to your  business, team, and leadership context. Partnership  – A thought partner (yes, sometimes PMM therapist) to talk through the tough calls, with empathy and clarity, so you don’t have to figure it out alone. This is why clients call me their “secret weapon” during transitions. Dozens of managers and leaders from companies like Square, Webflow, and SurveyMonkey have used this program to step into management with clarity and confidence, delivering results quickly while avoiding burnout. If you’re stepping into management for the first time, or you’re already leading but struggling to get alignment, this program will help you navigate that critical transition with confidence. 👉 Ready to lead with clarity? Book a call to get started. P.S. Here are the ways I can help you right now: 👉 For individuals: Job Search  – Land the right PMM role faster with my proven system for resumes, outreach, and interview prep. Choose the group program  or 1-1 coaching .  Onboard (IC or Manager)  – Hit the ground running in your new role with 1:1 coaching, frameworks, and support to deliver impact without burning out. Learn more. Thrive  – Already established? Get clarity on your next step, grow your leadership presence, and design the career you actually want. Work with me.  👉 For companies:  I partner with Marketing and PMM leaders to design and scale effective PMM teams, so they hire the right people, ramp them quickly, and establish product marketing as a strategic, valued function.   Learn more.