Hello, and welcome to the Courageous Careers newsletter, read by 4,000+ professionals looking to land, grow, and thrive in their dream product marketing roles.
Today’s special edition features some of the most frequently asked questions I get on job search and career development. I share:
What to do when you feel stuck in your career 🪨
What to do when you keep getting denied a promotion 💸
How to ace stakeholder/loop interviews 👩💼
If you are looking for part 4 of the series “How to build your product marketing strategy,” don’t worry - it will come out next month. You can read the previous three articles here.
With that…let’s dive in!
Let me work directly with your startup…
Recently, on LinkedIn, I announced that 🌟 I'm growing! 🌟 After years of helping individuals excel in product marketing, I'm expanding my focus to empower startups in building strong PMM functions.
Building a successful product marketing team in a startup is hard- especially now. The role's ambiguity, limited resources, and pressure to deliver quickly have left many young PMM teams struggling and founders doubting PMM's value.
That's where I come in. Over the past year, I've helped startup PMM teams:
Build a GTM launch process and hiring strategy. In 6 months, the PMM team grew from 1 to 4, significantly boosting conversion.
Develop US-market positioning in 2 weeks, enabling confident market entry.
Streamline team strategy to 3 key priorities, improving funnel metrics while keeping the team's sanity intact. 😂
Whether you need team coaching or fractional PMM advising, I'm here to help.
Please email me at peiyilin09@gmail.com if you'd like a free consultation.
Best of My Product Marketing Career Advice
Question 1: I've been at my current company for four years, and I feel stuck. It's not terrible, but I fear I'm just letting time pass. I'm unsure about my next steps or how to make a change. How can I create a career plan?
Deciding what to do next in our careers can be daunting. Many common fears hold us back, such as “What if I make the wrong move?” or “What if my next job isn’t perfect?”
Early in my career, I felt the same way. Despite feeling stuck in my consulting job, it took me nearly six years to make a change because I feared making the wrong decision.
So, the first step in any career planning is to let go of the idea that there’s only one perfect path. Instead, embrace the concept of a winding career journey with multiple possibilities—most of which are reversible and could lead you to exciting, unforeseen opportunities.
Once you've embraced this mindset, you can follow these steps to create a career plan:
Write your future vision story:
This isn’t about a specific job title or salary. It’s about envisioning your day-to-day life and how you want to feel. Do you want a work-life balance that allows for deep work in the morning and family time in the evening? Or do you see yourself leading strategy in a fast-paced company, working on high-stakes projects? Your vision should capture the essence of your ideal life.
Identify 2-3 potential paths:
Once you have your vision, identify a few potential paths to achieve it. Assess whether your current role aligns with your vision. For instance, if you imagine a 35-hour work week but are currently working 80 hours, you’ll know a change is needed. Your options might include switching jobs, changing teams, learning new skills, or exploring something entirely different.
Prototype your potential paths:
After identifying your options, test them as much as possible. The beauty of career paths is that others have walked them before you. Reach out to people in your network who have the roles/careers you’re considering. Conduct informational interviews to understand if those paths align with your vision. You can also test the waters by volunteering for related projects or taking on part-time work.
Choose the path that energizes you the most:
After prototyping, choose the path that excites you the most and feels easiest to start. Then, take the smallest, easiest first step to start moving in that direction.
Using this approach, my clients have successfully discovered fulfilling new directions. One client moved from big tech to a startup, became a freelance consultant, transitioned from PMM to Chief of Staff, and returned to school to become a creative writer.
While their new careers may not be perfect, one thing is certain: they are much happier.
I hope these tips help. For further reading, I highly recommend the book Designing Your Life, which is rooted in design thinking principles and has profoundly influenced my coaching style.
Question 2: I excel at work, but after three years, I'm still being denied a promotion and paid below market value. I like the company but feel undervalued. What should I do?
It's challenging to feel undervalued, especially when you're consistently performing well. To determine your next steps, consider the following approach:
Objectively evaluate your performance:
Assess your achievements and understand how your organization and manager perceive your contributions. Benchmark your level and pay against industry standards by reviewing market reports and talking to peers and mentors. This will help you determine if your compensation and role are aligned with your skills and contributions.
Understand your company’s promotion criteria:
If you've consistently received positive feedback in annual reviews but haven’t been promoted, it’s important to ask why. A good leader should provide clear reasons and outline the criteria for reaching the next level. Sometimes, a lack of promotion may be due to the absence of a business need for someone at that level, which may not reflect your performance.
Determine your options based on your values:
Based on your manager's response, decide on the best course of action. You might choose to stay, seek a different role within the company, or explore opportunities elsewhere if you feel undervalued. Ensure your decision aligns with your core values—such as learning opportunities, the caliber of colleagues, and your future career vision—not just extrinsic factors like title or compensation.
Move forward with focus:
If you conclude that the company no longer aligns with your values or doesn’t appreciate your contributions, it may be time to move on. In this case:
Clearly define your target, including the size of the company, business model, industry, and desired role.
Determine your value proposition for potential employers: Articulate in your application materials why you’re the best hire for those companies and what unique value you can bring.
Apply to those companies with a polished resume, cover letter, and direct outreach to hiring managers to maximize your chances of landing interviews.
Practice interviews using structured frameworks, like my PSAR framework, ensuring your answers reflect the level you’re aiming for, not your current position.
Negotiate your offer and title confidently based on your value and market rate.
Example: A client of mine, a founding PMM, was excellent at his job and asked for a promotion after over two years at his company. Despite clearly demonstrating his significant impact and crucial role in key projects, the company repeatedly refused to promote him, citing budget constraints.
After discussing his options with me, he decided it was time to move on. He quickly received an offer from another company with a 50% pay increase and a higher title—perfectly aligned with his career vision and values. When he resigned, his old employer immediately matched his new offer (!), proving there were no budget constraints—they had simply taken advantage of him.
While this situation may not apply to everyone, if you’re a top performer but are repeatedly denied a promotion, it’s likely time to evaluate new opportunities where your contributions are truly valued.
Q3: I am currently interviewing for new roles but I keep getting stuck in loop interviews with PMs and Sales. What should I do differently?
That’s a great question. Many people get stuck at this stage because their responses don’t match what their audience wants and needs to hear. Here are three steps to follow:
Step 1: Understand each stakeholder's perspective. Once you do, anticipate the questions they’re likely to ask.
Here are the two most common stakeholders:
👩🔧 Product Managers:
Product managers want to see your commitment to their product's success. Demonstrate how you've collaborated, championed products, helped prioritize roadmaps, or driven adoption through launches.
In startups, PMs may have misconceptions about PMMs. This is a chance to clarify what a great PM-PMM relationship looks like.
Potential questions:
Can you describe your product marketing experience?
How do you approach understanding a new product and market?
How do you develop a launch strategy?
How do you ensure product-marketing alignment?
If post-launch adoption is low, what steps would you take?
👩🔧 Sales:
In B2B companies, product marketing's relationship with sales is crucial (and sometimes contentious). Sales teams need to see your strategic value in the enablement activities that product marketing does.
Potential questions they might ask:
How do marketing initiatives support our sales goals?
What sales collateral will you provide?
How do you ensure product messaging resonates with our target audience?
How do you gather sales feedback on marketing materials?
What KPIs do you track for sales enablement effectiveness?
Step 2: Prepare your responses using a structured framework, such as the PSAR framework I developed:
In your answers, emphasize the role of the stakeholder team and how you collaborated with them, explaining the rationale behind your actions, not just the actions themselves.
When describing a work experience, follow this structure:
[Process] Outline your approach to show systems-level thinking.
[Situation] Briefly state the task, challenge, or goal.
[Action] Detail your actions, following the process you outlined.
[Results] Share the impact, results, and learnings.
Here is an example: Can you tell me a time you had to launch a product to market?
[Process] When I launch products, I follow a three-step process to ensure the best results. First, I validate the product/market fit to answer the what, how, when, and why of the launch. Then, I develop the positioning and messaging. Lastly, I determine the promotional and channel strategy, including internal enablement.
[Situation] Last year, I was tasked with launching a DEI tool to help SMBs track their diversity metrics easily. The goal for this launch was to drive pipeline for our sales team.
[Action] I first aligned with my PM counterpart to understand the target persona, problems we'd solve, and our unique benefit. I then created a brief capturing these details and identified positioning for the SMB market. After sharing this with cross-functional teams for buy-in, I developed the promotional strategy, focusing on educational webinars with industry experts rather than simply pushing product features.
[Result] We exceeded our launch target within the set timeframe. My launch playbook became widely adopted across the team due to this success.
Step 3: Finally, tailor your messaging by using the exact language each stakeholder uses.
For example, when speaking with product managers, use terms like "roadmaps," "adoption," "release/launch," "product development lifecycle," and "backlog." When speaking with sales, use terms like "deal cycle," "win rates," and "win/loss analysis."
You don’t have to do it alone.
I offer three programs that can help product marketers like you:
Land: My job search Blueprint Course to help you land your dream job fast (currently on sale!)
Grow: Succeed in your product marketing role in the first 90 days. Deliver value quickly and minimize stress.
Thrive: Thrive in your product marketing role. Achieve your career goals and get to the next level.
That's all for this issue. See you next time!