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  • PMM Job Search System | Courageous Careers

    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 Now The next enrollment window opens from April 13-17, 2026 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, a 1-1 coaching session, and a supportive 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 . If you're a PMM who's hitting walls in this job search, you're not imagining it. The market is harder than ever. There are fewer open roles, more qualified candidates competing for each one, and hiring managers are now testing for things that didn't exist in the last job cycle: AI fluency, broader GTM ownership, and the ability to do more with less. You have the experience and skills, but the rules have changed, and most job-search advice hasn't kept up. 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 April 17, and land a role before summer starts. 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!" Vivian Yu Senior Product Marketing Manager, LinkedIn If you're wondering whether or not you should take the plunge and join Yi Lin's PMM job search program, absolutely do it! Yi Lin's knowledge and guidance not only helped me land a PMM role during one of the most competitive job markets in history (February 2026) , but at a seniority level higher than I was previously (and after an extended career break). Not only did she help me stand out as a candidate, but her support and resources also up-leveled my skills as a marketer so I was more effectively positioned to excel in a new role. The insights I learned and relationships I developed as part of her program will continue to pay dividends for the rest of 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. April Yep Senior Product Marketing Manager, Datadog I enrolled in the program in October 2025 , and in less than two months, I landed an incredible role as a Senior Product Marketing Manager at Datadog, after months of struggling to gain traction on my own. The impact was immediate. After being rejected three times by the same company, my next application, using Yi Lin’s approach, turned into an interview within 24 hours , and ultimately an offer. Yi Lin is direct, thoughtful, and deeply experienced in product marketing. Her guidance is practical, honest, and incredibly effective, especially in a tough market. I’m so grateful. 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. Mihir Mandavia Product Marketing Manager, AMD Working with Yi Lin has been one of the most important investments I made in my career. In fact, one of the things my interviewers specifically called out was how much they appreciated the way I framed my answers and asked thoughtful questions, both of which came directly from Yi Lin’s program. That structure was the single biggest factor that helped me stand out and ultimately land my product marketing role [within 2 months] . What makes Yi Lin’s coaching unique is her ability to break down the PMM job search into actionable steps, while also helping you shift your mindset so you feel in control of the process. She doesn’t just prepare you for interviews; she equips you with tools to think like a PMM every step of the way. I cannot recommend Yi Lin enough. Her approach is strategic, practical, and genuinely transformative . 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 90+ 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. 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 What's Inside the Program The PMM Dream Job System combines 30+ impactful, bite-sized lessons specifically for the PMM job search you won’t find anywhere online. On top of that, you also get a 1:1 coaching session with Yi Lin, monthly group coaching calls, community peers, an accountability buddy and so much more. This is a program worth $12,000 offered for one-tenth the price , because my mission is to make a fulfilling PMM career within reach for everyone. Core Curriculum: Structured Lessons for Every Step 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 support system that accelerates your job search, keeps you accountable, and makes sure you don’t do this alone. Bonus 1 1:1 Coaching Session with Yi Lin (New!) Get a private, live 30-minute session with me to get unstuck and move forward with clarity and confidence. In this session, you’ll: Diagnose the biggest challenges blocking your progress Walk away with a clear, tailored job search strategy Get focused, actionable feedback on your most pressing need, whether that’s your resume, a case assignment, or how to tell a more compelling career story Bonus 2 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 3 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 4 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 5 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 6 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 7 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 [Bonus] 30-min 1-1 Session with Yi Lin ..................................................................................................(value $300 ) Get your biggest challenge unblocked directly [GUARANTEE] 30-day refund policy ......................................................................................................... (priceless ) if you aren’t satisfied with your experience (200+ alumni doubt it!) Total Value: $11,922 Your investment: $1,195 Or 3 payments of $450 Apply Now Enrollment for Q2 closes on April 17, 2026 Here is everything you will get in the PMM Dream Job System: 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 ) Total Value: $11,922 Your investment: $1,195 Or 3 payments of $450 Apply Now Application closes on April 17 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 90+ 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. I'm a career switcher with no PMM experience. Is this for me? This program is specifically designed for people who already have PMM experience, whether in a PMM title or a role with substantial PMM responsibilities. If you're making a full career switch into PMM with no relevant background, the curriculum will feel like it's ahead of where you are, and you won't get the full value. I'd recommend building foundational PMM experience first before enrolling. If you're unsure whether your background qualifies, the application is the right place to find out, I review every one personally. 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 in 2026. Apply Now Land Your Dream PMM Job in 30 Days—Risk Free

  • Land Your Dream Job Coaching | Courageous Careers

    Land your dream product marketing role faster with bespoke 1:1 coaching. Get personalized strategy, interview preparation, resume optimization, assignment feedback, and negotiation support from the most successful program for PMM job seekers. Land: 1-1 Job Search Coaching for Product Marketers Accelerate your job search and land the role you actually want. A bespoke 1:1 coaching program designed for experienced PMMs and leaders who want to navigate high-stakes job searches without wasted time or costly missteps. Book a Discovery Call Trusted by 200+ PMMs and leaders who’ve landed roles at companies like: Valentina Llinas Sr PMM at Cornerstone onDemand “You’re reading all these recommendations and think to yourself – 'Isn’t this too good to be true? Should I really make the investment?' The answer is, without a doubt, YES! Engaging in Yi Lin’s program is one of the most valuable investments I've made for my career. I had been in the hunt for 6 months already without luck, and by meticulously following her process (trust her process!), I was fortunate to secure a role that checked all of my boxes within just 2 months! I wholeheartedly recommend her program as an efficient way to maximize your time during the pursuit of your next role. The return on investment is substantial and will not only cover its own cost but also yield many times more in benefits. Run, don’t walk!” Landing a senior-level PMM role in today’s market is uniquely challenging. Roles are fewer. Expectations are higher, and hiring teams are more risk-averse and optimizing for very specific problems they are looking to solve. Which is why, at this level, strong experience alone isn’t enough. Most clients come to me after hitting one of these blockers: ✅ You are getting interviews, but not offers. You’re close, but something isn’t landing when the bar is highest. ✅ Your background is strong but non-linear. You’ve done a lot across roles, industries, or company stages, and your story feels hard to package cleanly. ✅ You were laid off and need to move fast. You don’t have time to experiment or “figure it out as you go.” ✅ You’re senior, but not coming across as senior enough. Your answers sound capable, but not decisive, specific, or with a sharp POV. ✅ You’re aiming for a strategic pivot (bigger scope, new industry, or different company stage), but you’re struggling to come across as competitive in this market. ✅ You’re tired of doing this alone. You want a sharp thought partner who understands the PMM market and will tell you the truth. If any of this feels familiar, you don’t need more generic job search advice; you need a sharper strategy specifically tailored to help you land high-visibility PMM-specific roles. How I help solve this I’ve coached 200+ product marketers through job searches and senior transitions, including Senior PMMs, Directors, and founding PMMs, and helped clients land roles from large tech to startups at companies like Datadog, TikTok, DoorDash, and Klaviyo. My work is especially effective for senior candidates with complex stories, competitive markets, or repeated “almost” outcomes, because I focus on the two things that matter most at this level: positioning and interview conversion. Together, we’ll diagnose what’s breaking down, sharpen your narrative, and help you convert interviews into offers. Specifically, I’ll help you: Clarify your target and candidate–market fit Build a sharp, differentiated story Interview with a stronger signal, specificity, and POV Win assignments and case studies without overworking Close the gap between final rounds and offers Negotiate confidently Book a Free Consult What my clients say Allie Allegra Director of Product Marketing, Algolia After getting laid off, Yi Lin became my guiding star during a very challenging transition. In just a few sessions, Yi Lin helped me distill my unique strengths and position myself effectively in a tumultuous and hyper-competitive job market, and provided insightful feedback, particularly when I faced complex assignment rounds. When I received an offer that left me uncertain, Yi Lin hopped on the phone right away, despite it being a Friday evening , to break down the pros and cons so that I could make a confident, informed decision. I HIGHLY recommend her to anyone seeking not just a coach, but a dedicated, empathetic partner in their professional development as a Product Marketer. Christine Moore Director of Product Marketing, Forj Before I connected with Yi Lin, I felt overwhelmed by the prospect of my next job search. Yi Lin helped me gain clarity through insightful coaching sessions, asking powerful questions that helped me define my ideal role and career goals. Her one-on-one approach felt personalized and supportive, like having a cheerleader in my corner. She's also cracked the code for writing cover letters that land interviews; she helped me craft compelling narratives that showcased my unique value proposition. The connections I made with other product marketing professionals in her community also allowed me to build a valuable network that continues to offer support and advice as I prepare to dive into a new role. I am grateful to Yi for empowering me to take control of my career and navigate the journey with clarity and confidence. She was a game-changer for me , and I can't recommend her services highly enough. Moyo Ajepe Product Marketing Manager (Strategy), Walmart Connect I wanted to pivot into a PMM/PMM adjacent role and had been working for months on my own to no avail. I even met with other PMM coaches but did not feel like they understood my goals. But then I found Yi Lin, and it has been one of the best career decisions I've ever made! She's incredibly flexible and took the time to really understand me and provide strategies on how I should approach my career pivot. The abundance of resources she provides, were instrumental in helping me. With her guidance, using her networking strategies, and a bit of perseverance, I was able to make a move into a role that finally aligned with my career goals! Not only is Yi Lin a well respected thought leader within the PMM space, but she's a great career coach! Thank you Yi Lin! Liza Ansher Product Marketing Manager, Amazon I'm not just saying this, I'm shouting it from the rooftops – if you're aiming for a thriving PMM career, Yi Lin is your secret sauce! In a few months of working together, I landed an offer and gained core PMM skills, critical thinking abilities, and a community that has set me up for future success. Specifically, Yi Lin's 1:1 coaching and async support significantly enhanced my interview and assignment performance and her resource hub, comprising of frameworks, guides, best practices saved me time and made me a better PMM, and finally, connecting with fellow participants in Yi Lin's program created a supportive PMM community for learning and growth amid the job search's highs and lows. If you are looking for a supportive coach on your career journey in PMM, choose Yi Lin! Josh Porter Director of Product Marketing, Kore AI I am thrilled to share my experience working with Yi Lin - as her guidance played an instrumental role in helping me secure a coveted Product Marketing Director role that aligned perfectly with my goals. My objective was to transition from an enterprise setting to a startup. However, given the tough job market, I found myself facing a lot of rejections despite my experience. The turning point came with Yi Lin’s guidance, which allowed me to stand out with a highly differentiated messaging. Additionally, her program allowed me to transform into a better product marketer - an unexpected but welcomed outcome of this journey. The comprehensive support I received—from group meetings and guest speakers to practice interviews—was pivotal in preparing me for the challenges of my new role. I express my deepest gratitude to Yi Lin and her client community. Job searching can be isolating, but with this program, I never felt alone. Eddie Radcliffe Sr Manager, Product Marketing, Circle I've had a GREAT experience working with Yi Lin. I was struggling to get a foot in the door for interviews, despite having over 10 years experience in consulting and product marketing. Yi Lin helped me turn around my key talking points from "what I want to say" to "what hiring managers want to hear"! Overall, it was a great experience in honing my background into very specific reasons why someone should hire me, as well as refining the companies I should target to immediately increase my success rate. Additionally, beyond the (abundant) frameworks and resources, I found our conversations invaluable and helped me to go from a "good candidate" to "the best candidate" - I landed a role within 1 month of working with Yi Lin! Alejandro Bellarosa Sr Director of Product Marketing, Varicent Yi Lin helped me get two senior-level offers in 10 weeks and completely redesign my core messaging and value pillars as a product marketer. She literally brought order to a chaotic search. More importantly, she is also an expert PMM strategist and has become a close advisor. Since starting my new role, she has advised me on my 30-60-90 plan and set my team strategy. I highly recommend her to anyone looking for an experienced PMM leader to help them find a new role, pivot to a different PMM category, and succeed in their role. She’s my new secret (but not so secret) weapon!! Prak Swamy Product Marketing Manager, Ownwell Yi Lin has been an EXCELLENT coach and guide. Her coaching program has been one of the BEST investments I have made for my career. She worked with me to create a personalized job search strategy and also taught me how to nail my pitch and tailor my application for each role. I followed her process to a T and was fortunate enough to land a great Full-Time role within few months of unemployment. More importantly (and this is what’s unique about Yi Lin), she also regularly checked in with me, going beyond her call of duty , was just always highly responsive on Slack to answer any questions I had and made introductions to peers/hiring managers whenever possible. She genuinely cared about how my job search was going. I HIGHLY recommend her program to make the best use of your time while looking for your dream role. The ROI will be worth it and will pay for itself and many times more. Peggy Pan Sr Product Marketing Manager, UnScreen Working with Yi Lin is one of the best decisions I made in my product marketing career. Her coaching helped me land a role in my dream field (even when the job market was so difficult). I chose to work with Yi Lin because she's clear about how she can help, and her advice is so on point. In every conversation I had with her, I could see tangible progress I was making to become a better PMM. One thing unique about Yi Lin is: in addition to her solid product marketing knowledge and experience, Yi Lin is very thoughtful and creative about her coaching approach. She constantly seeks diverse ways to help us grow through providing tools, masterclasses, and community building. After my job search, I decided to continue working with Yi Lin in my new role. Because I value her insights, and also because I truly enjoy this meaningful coaching relationship with Yi Lin. Read 90 more Testimonials on LinkedIn (Recommendations Section) What’s in the 1- 1 program? I’ve developed a proven PMM Job Search System that will serve as the theoretical foundation of this coaching program. On top of that, I’ll provide in-depth customization to directly support your specific situation, For example: If you are a leader or people manager , I can help you: Craft compelling narratives that highlight your leadership skills, from building teams to driving business impact. Tackle complex case studies with strategic advice that showcases your expertise. Build a targeted networking strategy to access the hidden job market and senior-level opportunities. If you are job hunting under a significant time crunch , I can help you: Quickly diagnose blind spots, uncover issues, and course correct based on what hiring managers are looking for. Develop a focused job search strategy that prioritizes high-impact actions. Offer moral support and actionable feedback to manage stress effectively. Explore alternative ways to secure income while continuing your search. If you are a career switcher , I can help you: Identify your transferable skills and your superpowers to build a powerful narrative for your ideal target companies. Learn critical PMM frameworks and apply them to your experience so you can discuss them convincingly in interviews and show you understand how product marketing works in your case studies. Identify roles with the most transferable entry points and build a transition path that can serve as stepping stones. Clients don’t invest in this because they “need help applying for jobs.” They invest because the cost of guessing is high, and the consequences of settling compound over time. This is an investment in landing a role that truly matches the next chapter of your career, often for less than one month’s salary at this level. 8 x 60-min 1-1 coaching sessions (incl. mock interviews) Full resume, cover letter, LinkedIn refresh 6 months of unlimited async document reviews between sessions 6 months of email/Slack support with 1 day turn around time A custom job search plan just for you Free access to my PMM Dream Job System Program worth $1,095, including: 30+ actionable lessons with templates, guides Live monthly group coaching calls My entire vault of workshop and coaching call recordings Access to a daily active private client community Access to a buddy system for accountability Investment: $6,500 Get Started Program details & investment This is a high-touch, end-to-end engagement designed to carry you through strategy, execution, and closing. FAQs What kind of return should I expect from this investment? For most senior PMMs, the real cost of a prolonged job search isn’t the coaching fee. It’s time. At the senior level, even one additional month of searching can easily represent $15K–$25K+ in lost income, not to mention momentum, confidence, and opportunity cost. In that context, this investment often pays for itself if it helps you land the right role even a few weeks sooner. More importantly, 1:1 coaching shortens the feedback loop. Instead of repeating the same missteps across applications and interviews, you get immediate calibration on what’s working, what isn’t, and why, so you can make better decisions earlier in the process. This isn’t about doing more. It’s about reducing wasted cycles and increasing precision in a high-stakes search. What happens after I book a call? The next step is a short, focused conversation to understand your situation and determine whether this level of support makes sense for you. On the call, we’ll talk through: your background and current job search status where things feel stuck or high-risk what kind of support would actually move the needle If it’s a fit, I’ll outline how we’d work together and what the engagement would look like. If it’s not, I’ll be honest and point you to a better option, whether that’s the PMM Dream Job System or something else entirely. There’s no pressure. The goal is simply to help you make a clear, informed decision. How is this different from the PMM Dream Job System? This 1:1 coaching is designed for senior PMMs and Director-level candidates whose job searches require custom judgment, not just a structured process. Most clients choose this option because: their background is complex or non-linear they’re operating at a higher bar (senior IC, Director, Founding PMM) they’re under time pressure and can’t afford trial-and-error they want direct, ongoing access to an experienced PMM leader This is fully bespoke, private coaching. Every decision from positioning, targeting, narratives, interview strategy is tailored to your specific situation. The PMM Dream Job System, by contrast, is a structured program with on-demand lessons, group coaching, and community support. It’s ideal for PMMs who want a repeatable framework and peer learning, but it does not include 1:1 support. If your search requires nuance, calibration, and fast iteration, this 1:1 work is the right fit. Why work with you instead of another job search coach? I’ve built and led multiple product marketing teams from scratch, across Series A startups through public companies. I’ve hired PMMs, evaluated senior candidates, and partnered closely with executives on business-critical decisions. That experience matters especially at the senior level. At this stage, hiring decisions aren’t about checking skills. They’re about: perceived risk clarity of thinking strategic judgment and whether your story makes you feel like the obvious choice My role is to help you position yourself as a solution to the company’s real problems, not just a capable candidate with experience. Ready to stop guessing and start landing the role you deserve? Schedule a discovery call

  • Ultimate Product Marketing Job Search Guide | Courageous Careers

    Get the Ultimate Job Search Guide for Product Marketers to help you land more interviews, position yourself as the best candidate, stand out, ace assignments, and navigate the entire job search process with confidence. Looking to land a PMM role in 2026? Download this 20-page guide for concrete frameworks and tactical guidance to navigate each stage of your job search. Take charge of your job search with 20 pages of insights distilled from thousands of hours spent coaching over 150 clients. By providing your email address, you'll also subscribe to my newsletter. You can unsubscribe at any time, and I respect your privacy. Valentina Llinas Sr. Product Marketing Manager @ Cornerstone OnDemand "I had been in the hunt for 6 months already without luck, and by meticulously following Yi Lin’s process (trust her process!), I was fortunate to secure a role that checked all of my boxes within just 2 months! The confidence that Yi Lin’s approach provides is priceless and game-changing." What You'll Learn How to tailor your search to your unique strengths, values, and competitive advantage. How to position yourself as the best candidate and understand the most strategic way to apply. How to ace your interviews and take-home assignment based on what hiring managers are looking for. Get Instant Access to the Ultimate Job Search Guide for Product Marketers Now By providing your email address, you'll also subscribe to my newsletter. You can unsubscribe at any time, and I respect your privacy. Why I created this guide Waves of tech layoffs have made it more important than ever to stand out in the job market. If you’ve been applying to dozens of roles and haven’t heard back or you keep getting passed up for more experienced candidates, it’s time to get more strategic. This ebook consolidates insights from hundreds of hours helping clients land product marketing roles. I hope it can help you avoid pitfalls and build confidence as you navigate your search.

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  • The Thriving PMM Framework: How to Build an Intentional PMM Career

    Before we dive into the main content, here is a quick announcement! If you’re a PMM stuck in your job search and tired of rejections, this is for you. I’m opening the next enrollment window for my ​ PMM Job Search System​  from April 13–17. 4 reasons to join this program: 1:1 time with me . You get a focused 30-min session to tackle your most critical blocker A proven, end-to-end playbook  with 9 modules and 30 lessons built specifically for PMMs Live workshops led by me , covering everything from resumes, interviews, case assignments, and even AI fluency A 300+ PMM private network , with alumni inside hiring teams and companies you want to work at On average, at least one member per week from the program is landing a job right now. If you’re serious about landing your next role, don’t miss this opportunity. :) 👉 Read the rave reviews and apply Now let's dive in. The question underneath all the noise Every week, I get some version of the same message. A PMM who is accomplished, capable, and clearly good at their work reaches out, wondering if they are building the right career for what’s coming next. Sometimes it’s driven by AI. Sometimes it’s a role that no longer feels like a fit. And sometimes it’s more vague, like a sense of being stuck or off track. Underneath all of it, the question is almost always the same. Am I actually in control of where this is going? And if I’m not, how can I be? When that question starts to surface, it is very natural to narrow your focus too quickly and look for answers in what feels most visible, urgent, or widely talked about. It creates a sense of direction, or at least the feeling of doing something productive. But this is usually where things start heading in the wrong direction.  Because you might begin making decisions that are not fully aligned with where you actually want to go, or you might optimize for what seems important in the moment, rather than what will meaningfully move you forward. Over time, that gap compounds. You can put a ton of effort into solving problems that don’t change your trajectory, and end up feeling more stuck because of it. I see this often in how PMMs respond to shifts like AI. There is a tendency to double down on tools or tactics when trying to address a deeper question about career direction, only leading to more frustrations and feelings of FOMO, or straight-up fear.  The PMMs who navigate through changes successfully approach this differently. They are not the ones chasing the newest or most talked-about trends. Instead, they’re the ones who have enough clarity about themselves to make intentional choices as their environment shifts. This is a pattern I have seen consistently across the 300+ PMMs and leaders I have coached, regardless of company, level, or market conditions. It is also what led me to develop the Thriving PMM Framework. The framework is a way to think more systematically about how you build your PMM career.  It has three layers:  Layer 1 focuses on PMM craft , the core skills that define the role, which are now increasingly augmented by AI.  Layer 2 is about  human skills , the capabilities that carry across contexts and are not easily replicated by tools. Layer 3, which sits at the foundation, is your  career agency . This is your ability to define your path, shape your story, and navigate key inflection points with intention. Today, I’ll walk through each of these three layers to help you get clearer on where you are and what actually matters next. Let’s dig in.  Layer 1: The core PMM skills Let’s start with the first layer, PMM craft, because this is where most of the noise is right now. First, let me reassure you. The core PMM craft isn’t going away. If anything, AI is raising the bar for quality, which means the fundamentals matter more than ever. In fact, from what I’m seeing in my own advisory work, demand for positioning and messaging has actually increased, not decreased. What is changing is how the role shows up. AI is pushing PMMs further into orchestrator roles, where you are coordinating work to improve efficiency while keeping the strategy intact.  To use music as an analogy, as the conductor of an orchestra, you are not playing every instrument yourself, but you are responsible for how it all comes together. That requires a strong understanding of what each instrument can do and how to bring them together in a way that actually works. Ultimately, that is what determines the quality of the performance, and is what separates great world-class philharmonics from the rest.  So what are the core elements of the PMM craft? Here is a refresher on the four foundational elements: Research.   Deep competitive, market, and customer research. The insights that move strategy. AI can synthesize faster, but you still need to make judgment about what to pay attention to and what’s just noise.  Positioning and messaging.   Turning insights into a clear narrative that resonates. AI can generate options, but you need to shape what’s actually true and differentiated that doesn’t sound like everyone else. GTM systems.   Building the operating model for launches, campaigns, and go-to-market strategy. AI helps with execution; you still need to design the architecture, often  in collaboration with other humans.  Enablement and evangelism.   Making sure the message lands internally with sales and externally with the market. AI can help with content; but again, the relationships and influence are human. Of course, these don’t cover every responsibility a product marketer might have. The scope will vary depending on company stage, size, and go-to-market motion. Some PMMs will own pricing and packaging, while others focus on analyst relations or even in-product activation. But these four areas form a core foundation. Without them, it is difficult to build real strength in the role. In summary, the right way to approach AI is to treat it as an execution accelerator across all the core PMM craft elements. It increases the speed and volume of work, making judgment and prioritization even more important. The table below breaks this down more concretely across human-led, AI-assisted, and AI-driven work. Table: How PMM work shifts across human judgment and AI support (not exhaustive) 👉 If you want to go deeper on how to use AI in your daily work, check out my comprehensive State of AI in Product Marketing Report . Layer 2: The human skills no tool can replace If Layer 1 is about the work itself, Layer 2 is about how that work actually gets done. I was recently talking with a Lead PMM at a large tech company who was hired to own her company’s platform AI narrative. Her role is entirely centered on AI. But when I asked what actually makes her successful, she didn’t mention tools or technical depth. She said it was her ability to build relationships, align teams, and get people to believe in what they’re building. The irony wasn’t lost on either of us. The most important skill of an AI PMM is, in fact, irreducibly human.  Here are the two skills that are fundamental to being a great PMM that AI simply cannot replace:  Influence and relationships.   This is one of those areas that can sound almost cliché, as “Influence without authority” gets talked about a lot. But in practice, it is still one of the most important skills to get right. Influence is your ability to build trust across all stakeholders, such as product, sales, leadership, and customers. It shows up internally, in how you align teams and drive decisions, and externally, in how your message lands in the market. It also requires judgment, e.g., knowing which battles to pick, when to push, and how to bring people along. Because let’s face it, this is what determines whether your work actually gets implemented and seen.  👉 If you want to go deeper on this, I’ve written an entire newsletter on this topic that you can check out here Business strategy.   This has always been critical for PMMs, but it is now more important than ever. Because as AI takes on more execution, the work becomes even more about deciding what is worth doing in the first place, and why… and that is business strategy. You need to understand how the business operates, connect your work to revenue, growth, and company priorities, and prioritize ruthlessly and communicate trade-offs to leadership. This is what separates strategic PMMs from tactical ones: the ability to work one hour with product management, hop on a customer call with CX, and then present a deep dive on the competition to the leadership team, all while thinking about the business as a whole, and not just that particular piece of it. 👉 If you want to go deeper on how to connect PMM work to business strategy and growth, I’ve written more about that here The bottom line is, PMM is a connector role between many different functions, and success depends on navigating people as much as it does on producing work. It requires emotional intelligence, judgment, and a strong understanding of how the business operates, along with the ability to align across different priorities. None of that can be automated. The image below shows how the PMM role works in practice,  not as the center of teams, but  as the connector across them. Layer 3: Career agency as the foundation  If Layer 1 is about the work itself, and Layer 2 is about how that work gets done, then Layer 3 is about the direction you’re actually heading in. This is the layer most PMMs don’t spend enough time on, but it is the one that makes everything else work. There’s a chart I often share when I give a talk about PMM career design at conferences: Most people who see this focus on the winding parts, aka “my second act”: the startup that failed, the art business, the pivot into product marketing, etc.  What they don’t always notice is what the straight line (blue area) at the beginning actually represents. That was me with low career agency. I was an engineering consultant out of Georgia Tech, moving predictably upward, but unhappy. Even though I knew early on I didn’t want to be a consultant, I stayed for 6 years anyway, mostly out of fear and uncertainty.  What changed wasn’t that I suddenly had a perfect plan. It was that I started treating my career as something I was actively designing, rather than something that was happening to me. Once that shifted, the path became more nonlinear, but also more intentional. The startup that didn’t work, the stint in content marketing, the art business, they stopped feeling like detours. Each one gave me information and shaped what I did next. And over time, that led to outcomes that would have been very difficult to plan up front. i.e., moving to PMM, being promoted three times in three years to Director, building teams from scratch, and eventually creating a portfolio career that spans coaching, advising, and my art business (and living perhaps the most fulfilling phase of my career)  If you’re curious, I once wrote a “resume of failure” that captures a lot of these pivots and detours. I share this because it’s what career agency actually looks like in practice. I also share this to show you that no matter where you are at one point, you can change it and take control of it.  Career agency is not just about having skills. It’s about being the primary driver of your own career, making decisions even when it’s hard, evaluating trade-offs, and moving in a direction that aligns with what you actually want. In practical terms, career agency consists of skills that empower you to do the following:  Path design:   Getting clear on where you actually want to go, whether that’s leadership, a deeper IC path, a portfolio career, or something you can’t quite name yet. There’s no right answer because it’s about you, and your unique journey. Landing the right role:   Knowing how to articulate your value clearly, finding roles genuinely aligned with that, and finding a role that maximizes growth and what you value instead of settling for any offer that comes along (or other people’s definition of good). Thriving once you’re in it:   Having a real playbook for the first 90 days, knowing how to position yourself for promotion, and building the internal relationships that actually move your career. Building optionality:   Designing a career that goes beyond the current job, which includes your personal brand, your network, and the reputation you’re building in the market. This is the work you do for yourself, not just for a company’s roadmap. To give you an example, one of my clients came into our first session and said, “I don’t even know what my career goal is.” So we actually spent that first session just clarifying that. And what she realized was that she didn’t want to be a full-time PMM anymore. She wanted to build her own business. From there, we spent the rest of the program building out her business idea, her offer, and her entire GTM strategy, including how she would test and get her first clients. Within two months of launching, she had already signed a major client. That’s what I mean by career agency. Because it doesn’t matter how strong your skills are or what others perceive as success. If you don’t know where you’re going or are just following others’ playbooks, you can end up just rowing harder in the wrong direction. That’s why this layer sits at the foundation of everything else. What’s next - Start building your PMM career with intention If you’re reading this and it’s making you think more seriously about your own direction, this is the work I do and have been doing.  I’ve worked with experienced PMMs across different stages, whether they’re trying to land a new role, get promoted, or figure out a bigger shift in their career. But I also know that when you’re at that point, you might not even know what the right next step is, or which program makes sense. That’s why I am offering a limited, one-time Career Clarity Session. This is a focused session where we look at where you are today, assess what’s actually going on across these different layers, and help you get clear on what your next move should be. This is a good fit if you’re a mid-career PMM: thinking about a new role or promotion feeling stuck in your current role or trying to figure out where your career is actually going This offer is valid only for the next 2 weeks.  → Learn more and apply here And if you’re wondering what this looks like in practice, here are a few experiences from PMMs I’ve worked with:  That’s all for today! See you next time.  Yi Lin

  • The 5-Step Product Positioning Playbook for Product Marketers

    I've spent years running positioning workshops and training PMMs across companies of all sizes. Before each session, I ask these teams to rate their current positioning process on a scale of 1 to 5. The pattern is remarkably consistent. Most teams rate themselves somewhere between 2 and 3. I rarely see 4s, and almost never see 5s. And these aren't struggling teams. They're talented, experienced product marketers. They have strong frameworks and know April Dunford’s process inside and out. They care deeply about getting it right. But they feel stuck, because positioning is hard.  AI has made it even harder. Categories are saturated,  and differentiating your solution is more important than ever. In fact, the ability to create differentiated positioning supported by strong narratives is one of the MOST important skills hiring managers today are looking for.  So if you feel like you or your team haven’t quite “figured out” positioning or that output is less than ideal, you're not alone.  Let me walk you through why it fails and what actually fixes it. Why product positioning fails 1. Positioning gets created in isolation or diluted by committee. These are two common patterns – both extremes, and neither is good. In the first, a PMM creates positioning on their own. Stakeholders weigh in randomly or through ad-hoc meetings, but there's no space made for shared conversation. In the second, teams go too far in the other direction –  trying to build consensus by incorporating everyone's feedback, and losing the positioning’s edge and clarity in the process (the peanut butter approach). Read about it here .  Both approaches miss something fundamental: positioning is an alignment exercise , not a solo deliverable. The goal isn't to write the perfect statement and get approval. It's to create shared understanding across the people who need to use it. 2. Positioning is treated as a launch deliverable instead of a strategic input.  This often happens when product management doesn’t understand the product marketing function.  They see positioning as something that happens at launch: features get built, decisions get locked, and then PMM comes in to explain it all. This is actually the wrong order of operations. Positioning works best when it informs product development, not follows it. Early positioning creates clarity on what the product does and who it's for. That clarity shapes better decisions. Positioning that comes after decisions are made is reactive: you're explaining features without knowing if they matter to customers. It evolves in stages: Discover  — before a line of code is written, pressure-test your right to win. Design  — refine value pillars as the product takes shape. Develop  — lock the narrative before launch. Deploy  — activate it across messaging, channels, and sales. When positioning informs the roadmap early, you build the right thing. When it’s layered on at the end, you’re just trying to explain it. I break this down in more detail here .  Also, see the chart below to represent this.  3. Teams focus only on the positioning statement itself, not what feeds into it or what happens after. Most positioning conversations stay narrowly focused on crafting the statement – skipping  two critical pieces get skipped: The inputs:  What data and insights should actually inform positioning ? Some good news: most teams already have the research they need to start. The activation:  How will you translate positioning – first into messaging, and then sales conversations, on product pages, in customer onboarding? Without a clear activation plan, even great positioning sits unused. These three problems feed into each other. Positioning stays misaligned across teams, sales doesn't use it, Product and PMM aren't aligned, and positioning becomes a box you check off rather than something that shapes business operations and helps you grow. A strong positioning process – the one I’m about to walk you through – can solve all three at once. It’s not just for writing a statement, but a system for how to make sure it gets used throughout your organization. Before we dive in, let’s quickly reset on some commonly used but often misunderstood terms:  Positioning, messaging, copy, and narrative Before we dive into the process, let's get clear on what we're actually talking about. Positioning  is your strategic foundation. It's how your product fits in the market: who it's for, what it does, why it's different, and why it matters. Think of it as the internal logic that guides everything else. Messaging  is how you communicate your positioning. It's the language, themes, and key points (value pillars, benefits, capabilities, and features) you use to convey your value to customers.  Copy  is the execution. It's the actual headlines, body text, CTAs, and specific language that shows up on your website, in emails, in ads. Copy brings messaging to life and can be clever, punchy, or creative.  Narrative  is the story arc that connects your positioning across touchpoints. It's how you guide customers through understanding your value over time, from first awareness to deep conviction.  You can think of these as layers of the onion with positioning in the middle – and if the center is not right, then everything falls apart,  no matter how great your copy is. That’s why it’s so critical to get it right.  My 5-step product positioning process  I've been refining this process for years across companies of different sizes, stages, and industries. It's designed to fix the positioning mistakes we just talked about: create the right amount of alignment, bring PMM in earlier, and give teams a repeatable system. This is a mixed-method approach, not pulled from a single playbook but instead influenced by some of the strongest positioning frameworks (including April Dunford’s), combined with what I’ve learned from running workshops and leading PMM within organizations. I’ve used it to train dozens of teams and individuals.  Step 1: Gather data and insights Notice I didn't say "do more research." I said, gather what you already have. The goal here is to determine the least amount of data needed to come up with the best possible insights to inform positioning. This does NOT necessarily mean conducting more customer interviews, competitive analysis, or market research. Because you probably already have enough insights to move forward. The problem is that no one has synthesized these insights in a way that's useful for positioning. So how do you do this with the least effort?  Start with the end goal in mind First,  get clear on what you're trying to inform. You need to understand: Market segmentation and ICP Personas, use cases, and jobs to be done Differentiated value Customer proof (if it exists) Keeping these goals in mind helps you figure out which insights actually matter. Use the triangulation method Here's the framework I use: instead of gathering a ton from one source, mix your data types. You’ll get better coverage, reduce bias, and have more usable data. Think of it as a triangle with three types of data: Qualitative data (what people say):  Customer interviews, call recordings, online reviews. You don't need dozens; just two to three will usually surface 80% of what you need to know. Outcomes data (what they choose):  Customer acquisition cost, NPS, churn rates, conversion rates. These give you directional clues about what's working and what isn't. Behavioral data (what they do):  Usage analytics, feature adoption, onboarding completion rates – how customers actually interact  with your product, not just what they say they do or plan to do. Mixing these types rather than going deep on just one will give you a more accurate picture than 50 interviews alone. . Step 2: Conduct the positioning workshop This is where the magic happens, and it's not a solo exercise. A positioning workshop brings cross-functional stakeholders into the same room (or Zoom) to speak the same language about the product's value. You absolutely need product in the room;  sometimes sales, sometimes customer success. The exact mix and seniority levels needed depends on your org, but the point is: this isn't something PMM does alone and then presents. The workshop format works because it  forces alignment and focus in real time.  Instead of endless Slack threads and comment wars in Google Docs, you hash it out together. Disagreements will surface, but you resolve them in the moment. Product teams start thinking about capabilities and outcomes, not just features. Sales starts understanding the strategic rationale behind the messaging. Everyone leaves speaking the same language. It builds buy-in without authority. As a PMM, you often don't have formal power over product or sales. But when you facilitate a strong workshop, you demonstrate influence. You become the person who brings clarity to the chaos. The structure of the workshop matters. I use a set of forcing questions and exercises designed to pull out what people actually know (and reveal what they don't). These are listed below..  1. Start with your happiest customers   Ask: Who gets the most value from us?  This is where alignment gaps show up. If there’s no consensus on your best-fit customer, everything downstream breaks. 2. Identify the champion persona   Within the ICP, who actually drives the deal forward –end user? Budget owner? Executive sponsor? Sharp positioning requires a clear champion. 3. Clarify their jobs-to-be-done   What is the champion trying to accomplish? What motivates them? What gets in their way? 4. Define the real alternative   If you didn’t exist, what would they do instead? It might be another vendor, a workaround, or nothing at all. Pick one. Positioning needs a clear reference point. 5. Pressure-test differentiators   What truly sets you apart from that alternative? Some claims will be table stakes. A few will emerge as real competitive strengths. 6. Build the value matrix (post-workshop)   Translate differentiators into impact:  Attribute → Capability → Benefit → Business Outcome  This connects product details to what the champion actually cares about. 7. Synthesize into a messaging house   Bring it all together: • ICP & champion • Core challenges/jobs • Differentiators & value pillars • Proof & business outcomes Tools like Miro or FigmaJam boards are best for this kind of exercise, whether in person or virtual, as a way to truly preserve the work you’ve done (see visual below). Of course, positioning can't just live in your head or be buried in a slide deck. You need to document it in a way that's accessible, reusable, and clear. That's where the positioning and messaging canvas comes in. It's a structured document that captures not just what you decided, but why you decided it. Step 3: Capture into a positioning and messaging canvas The centerpiece of this canvas is the value hierarchy exercise. This is where most teams get stuck, and it's also where the biggest breakthroughs happen. Here's how it works. You map your product across four layers: Features : What it is. The tangible pieces of your product. Think: dashboard, API, mobile app. Capabilities : What it does, and enables users to do. Think: track performance in real time, automate workflows, and centralize data. Benefits : What it means for the user – capabilities translated into value. Think: save time, reduce errors, increase visibility. Outcomes : The transformation or business result. Think: grow revenue, improve customer retention, scale operations. Example Value Matrix of a Fake B2B SaaS AI platform Features Capabilities Benefits (User-Level) Outcomes (Business-Level) AI-powered anomaly detection Automatically identifies unusual patterns across revenue, usage, and churn signals Teams don’t need to manually monitor dashboards Faster issue detection → reduced revenue leakage Natural language data queries Allows anyone to query data in plain English Non-technical teams can self-serve insights Increased data adoption across departments Predictive forecasting engine Projects revenue and usage trends based on behavioral patterns Leaders can anticipate risks and opportunities earlier More accurate quarterly planning and resource allocation Most common teams jump from features straight to benefits, completely skipping the capability layer. But capabilities are the bridge that connects what your product is to why it matters. Without that bridge, your positioning feels hollow. You're making claims ("save time!") without showing how the product actually delivers on them. When I have teams fill out a matrix with these four columns during workshops,  the capability row is always the hardest and the most revealing. It forces product teams to articulate what the product actually does before they start making promises about what it means. Once you've mapped the hierarchy, you capture it in the canvas alongside your target audience, competitive differentiation, and proof points. This becomes your source of truth. Step 4: Test and validate Before you roll out positioning across the org, you need to pressure test it. This helps during the workshop when stakeholders disagree too much on positioning decisions; you can say, "Look, we're not trying to create perfect positioning here. We have to test this anyway." That speeds up the process instead of three months of back and forth. Because positioning is a hypothesis . It's what you think is best, but you can’t validate until you see how your audience actually responds to it. Three ways to test positioning Below are three practical ways to validate your positioning. First, direct discussions with customers  (especially powerful in B2B). Have salespeople use the new positioning directly in sales deals. See what resonates, what confuses, and what questions customers ask. Second, panel research . For B2B, Wynter is a tool that's widely used. User testing platforms work well, too. Get direct feedback on whether your positioning is clear to your target audience. Third, direct channel testing . Test it across your marketing channels. A/B test emails. Try different social copy. Put variations on your website and see what performs. You’re doing this; just apply it to positioning. The key insight is that testing doesn't happen once before launch. You test, learn, refine, and test again. You can create something,  validate it in the market, iterate, and do it again. This mindset also helps you move faster. When teams get stuck debating positioning details, remind them that the market will tell you what works, which beats endless internal debates. Build the hypothesis, test it, learn from it, and refine – here’s how.  Step 5: Activate and iterate This is where most teams drop the ball. They create the positioning, share the document, and then… nothing happens. Sales keeps using their old pitch. Product keeps talking about features. The problem is simple: it’s not obvious to other teams l how to actually use your positioning document.  So you need to create derivative assets for each team. For marketing, create a quick reference guide for copywriting. What to say, what not to say. Specific phrases. Examples of off-brand language to avoid. For product, create a strategic insights brief. Share the competitive intel and customer feedback that can inform their roadmap. For sales, develop the actual talk track. The pitch, the objection handling, and the proof points they can use in customer conversations. The more directly you answer their questions, the better adoption you get. And when you help them, something powerful happens: they start helping you back. The teams that treat positioning as locked either stick with outdated messaging or reinvent everything from scratch every six months. Both are painful. Instead, build a rhythm. Make positioning a part of how your organization operates. How this process brings in PMMs earlier (and earns you a seat at the table) A  strong positioning process doesn't just improve messaging. It changes when and how PMMs get involved in product decisions. Right now, if you're like most PMMs, you're brought in after product decisions are made. The roadmap is set. Features are locked. Your job is to "make it sound good." But when you establish positioning as a repeatable process, not a one-time deliverable, it becomes a forcing function. Product teams start to realize they can't ship without clear positioning. And positioning can't happen without PMM. Here's how to use this as leverage: Make positioning a requirement, not a nice-to-have . Explain why it’s a critical input to the product development cycle, not an afterthought. When Product proposes a new feature, ask: How will we position this? Who is it for? What value does it deliver? Show how positioning informs product decisions . Use the value matrix exercise with product teams before features are built. If they have trouble articulating a feature’s capabilities and outcomes, they start questioning whether it's the right thing to build in the first place. Create a repeatable rhythm . Don't wait for launches to do positioning work. Build it into your quarterly planning. Make it part of how product and marketing operate together. The positioning workshop itself becomes your leverage. When you facilitate a strong session that brings clarity and alignment, people notice. You become the person who makes the complex simple. You demonstrate strategic thinking, not just execution. That's how you earn a seat at the table: by proving you belong there through the value you create. What’s next If you see yourself and your team in what I’ve described above, you don’t have to fix it alone. Here's how I can help: ​ 1:1 coaching ​ for PMMs looking to elevate their positioning work, influence without authority, and become true strategic partners - not just launch support. ​ Team training and advising ​ for companies that want to build a great positioning, especially for navigating complex positioning challenges, multi-product portfolios, or major strategic shifts. Simply contact me if you are interested, and we can discuss how to work together.

  • Four Lessons from Four Years as a Product Marketing Coach

    This newsletter is sponsored by: UserEvidence Turn customer proof into your competitive advantage  If you want your team to strengthen messaging, compete harder, and win more deals in 2026, start by fixing your customer evidence engine . As a former Director of PMM, this is the system I desperately wish I had. UserEvidence  gives you the verified proof every PMM needs but never has enough of: ROI stats, competitive wins, product claims, and account-level stories you can plug directly into launches, narratives, and sales motions. With the ability to scale customer-centric content, you can dedicate more time to actually enabling sales.  → Book a demo to see it in action! Four Lessons from Four Years as a Product Marketing Coach Happy New Year, everyone!  I hope 2026 is off to a gentle, grounding start for you. 🥰 The end of a year/beginning of a new one always puts me in a reflective mood. It is one of the few moments when time feels slow enough to pause and really take stock. I think about what worked, what didn’t, what surprised me, and what I learned the hard way. This year marks my fourth year running my own product marketing coaching and advisory business (or 5th year if you count my side-hustle year). It has been an incredible journey. There have been real highs, plenty of challenges, and constant learning. I feel deeply grateful that I get to wake up every day doing work I care about, working with thoughtful, driven people, and building something that supports my family.  But that doesn’t mean it has been easy or linear.  I’m sharing this reflection because I’m often asked how I started my business or how I built what I do today. From the outside, things can look smooth or “figured out.” The reality is a lot messier and slower. And to me, there’s nothing more encouraging than hearing how things went “behind the scenes” when people share their success stories.  Because our career successes are not magic, and that means whatever you want to achieve, it can happen for you, too.   So here we go.  Lesson 1: Mastery beats motivation  Many people are familiar with parts of my story, but for those who aren’t, here’s the short version. I started my career as a transportation engineering consultant and later made a hard pivot into product marketing. It was intense and challenging, but it worked. After becoming a newbie PMM, I was promoted three times in three years to become a Director of Product Marketing.  After building several PMM teams from scratch, I decided to go out on my own. I’m sure I looked confident from the outside – but I did not feel  ready at all. During COVID, I helped several laid-off friends land new jobs, and that’s when I started to notice that I was exceptionally good at helping people make sense of their experience and turn it into a clear, high-impact story. It was the same skill I had relied on to change my own career. These friends pushed me to take the work more seriously, which eventually grew into my 1:1 coaching programs. At some point, as my business grew, I wanted to reach more people, so I decided to build a job search course. I spent a huge amount of time on it, creating the curriculum, recording videos, and so on. But when I launched it, only five people signed up. I remember feeling embarrassed and disappointed. I thought that the idea was never gonna work and pretty much gave up. But after sulking for a week, I decided I couldn’t quit yet.  I knew from plenty of people that my process worked…. So why didn't anyone sign up?  Instead of giving up, I got curious. I paid close attention to those five people. Where did they get stuck? What actually helped? I also talked to people who had considered signing up but didn’t. As I collected feedback, one insight immediately stood out: job search support cannot be purely self-paced. People need accountability, real examples, feedback, and community. That realization changed everything and helped me launch the PMM Job Search System in December 2024.  Over the past year, more than 75 people have gone through the program, with an average of 1 person per week landing a new job. None of this would exist if I had treated those first five sign-ups as failures instead of information. This was a huge lesson for me that I will carry forward:  The most meaningful things rarely look impressive at the beginning. Mastery is built through repetition, humility, and a willingness to keep going. Lesson 2: Clarity beats noise When you are building anything, whether it’s a business or a career, it’s like rowing a boat. If you don’t know where you’re going, all that effort just moves you in circles. Early on, I spent a lot of time thinking about what kind of business I actually wanted to build. I was raised by a single mom with very strong values, and I’ve always had to reconcile two things that can feel at odds: creating real value for people and being paid fairly for my work. I wanted to help people generously, but I also needed to support my family and build something sustainable. What became clear to me quickly is that I didn’t want to build a business optimized purely for short-term revenue. I wanted something enduring: a business grounded in impact, trust, and long-term relationships. I believed that if I focused on that, the money would follow. Not the other way around. That clarity made some decisions harder in the moment. I had to learn to turn away clients. I said no to opportunities that looked good on paper and ignored paths that promised faster growth but didn’t feel aligned with my true goals. I see this tension most clearly on LinkedIn. There are moments when I spend days creating a post, only to watch it land with 20 likes. Then I see a meme rack up thousands of likes. I’d be lying if I said that never stung or made me question my approach. The comparison mentality is real.  But I always come back to the same question: what am I actually trying to build? That question has helped me ignore noise and focus on signals that matter more to me. Not just revenue growth, though that’s important. What I care most about are repeat clients and word of mouth. Those are indicators of trust and durability. Last year, nearly 40% percent of my work came from repeat clients across my programs, along with a steady stream of referrals from people who know me and my work. Those results have given me a deeper kind of confidence that comes from knowing this:  Sticking to my values will always lead to the right results.   Lesson 3: Focus, but leave room to experiment  I’ve always believed deeply in focus. As product marketers, we know this instinctively. If you try to do everything, no one knows you for anything. Focus is what allows mastery to form. For most of my career, I leaned very hard into that principle. And it served me well. What I learned more recently is that focus alone isn’t enough. Over the past year, I started thinking about my work through an 80/20 lens. 80% of my time went into refining and deepening my core offerings. The remaining 20% I treated as R&D. This 20% was uncomfortable by design because I needed to put myself out there, to try things I wasn’t sure would work, and to be willing to face rejection. In a world that’s changing as fast as ours, doing only what has worked in the past is one of the fastest ways to become irrelevant. And not surprisingly, about 90% of those experiments failed. I was ghosted after proposals. Conversations that felt promising went nowhere. Ideas I thought had potential turned out to have no real product-market fit. But those failures were incredibly informative. They taught me what not to pursue and sharpened my instincts. The remaining 10% did  surprise me. For instance, I helped an AI startup create their  positioning and messaging  for expansion into the US market, I trained a team of 70 PMs and PMMs to align on how to work together (yay!), and I built a recruiting agency !  So by putting myself out there, I got opportunities that kept me sharp, exposed me to new problems and perspectives, and opened up new business ideas. Lesson 4: Getting help > going at it alone  One of the most important lessons I’ve learned is that growth gets much harder when you try to do it entirely on your own. Not because you don’t know what to do, but because the most meaningful problems require new perspectives and support. I’m actually introverted, even though people often assume otherwise. Writing has always been my most natural way to connect, which is probably why you’re reading this newsletter. 😀 But introversion can also turn into isolation if I am not careful. This year, I pushed myself to change that. I reached out to people I admired and deepened relationships I already had. Those small actions led to some of the most meaningful relationships I’ve built so far: mentors, collaborators, peers, and partners who challenged my thinking and expanded what I thought was possible. For instance, I deepened my relationship with my mentor  - the amazing Martina Launchengco, whom I met on LinkedIn through one cold outbound message. She has been a huge collaborator and inspiration since then.   But support doesn’t just show up in professional settings. I’m often told I’m a “super mom” for running a business while raising young kids. The truth is, I couldn’t do this alone. I have an incredibly supportive partner and a strong support system at home. There is real, invisible labor behind everything I’m able to build, from help with childcare, logistics, and the emotional weight of day-to-day life.   The more honest I’ve become about needing help, at work and at home, the more sustainable my life and business have become. Growth has accelerated not because I worked harder, but because I stopped pretending I had to – or could  – do everything myself. As I look ahead to 2026, one of the biggest bets I’m making is on people. Who I work with. Who I learn from. Who I partner with. Who supports me behind the scenes. Even as a one-person business, nothing I build is truly solo. Looking ahead to 2026 As I reflect on the past four years, I feel deeply grateful. Not just for the growth of the business, but for the life it has allowed me to build. My oldest daughter is four and a half. My youngest is ten months old. This work has supported my family, stretched me as a person, and given my days meaning. It hasn’t been easy. It still isn’t. But it has been worth it. If I can leave you with one thought as you step into 2026, it’s this: get honest about what you really want to build in your life.  Then ask yourself what one small step you can take right now to move toward it.  There is a saying I love, which is “too small too fail” . If you take a small enough step forward, even if it’s absurdly small, then you can’t fail (and will only move forward).  So take that step. May be that is getting clarity about what you want. May be it’s leaving something bad behind to pursue something new. Or may be it’s simply asking for help.   That belief is at the heart of everything I do at Courageous Careers. I hope some of what I shared was helpful to you.  I’m glad you’re here. Thank you for reading. I’m rooting for you this year!! Yi Lin P.S. If this newsletter has resonated with you, and you’d like to build an intentional career with the right support in 2026, here are all the ways I can help you:  Looking to land a new PMM role?  → Join the PMM Job Search System  (Q1 enrollment opens today!) or check out my 1-1 coaching program Starting a new PMM job and want to ramp fast?  → Check out my 1-1 PMM Onboarding Program Want to thrive, get promoted, or gain clarity in your role?  → Check out my 1-1 Leadership Coaching Program Need support for your PMM team or company?  → check out my advisory, consulting, and training services

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