June 3

Deep-Dive: Navigating your Product Career

The product management career path is certainly a tricky one. I often say that none of us went to school for product management (which is changing these days). But even today, the lack of a formal product management education means that oftentimes, product people find themselves questioning whether their career decisions are the right ones. There is a path for Product Managers – but that path to success is rarely a straight line, and the skills that got you to your current role may not be the same ones that will propel you to the next level.

But what if you could learn from the triumphs and tribulations of seasoned product leaders who have walked this path before you?

In the past, we’ve hosted product leaders like Gibson Biddle (Former CPO at Netflix and Chegg) and Jackie Bavaro (Author of Cracking the PM Interview and Cracking the PM Career), and they’ve shared a lot about how Product Managers can elevate their careers in product management. In this essay, we’ll dive into much of what they’ve taught – including the career progression of a Product Manager and Product Leader – from the early days of mastering execution to the leadership challenges of driving organizational excellence. We’ll dig in on how to elevate your career strategically through the projects you take on and the people you keep in your life. 

Of course, there are almost always setbacks we’ll have to endure within our careers. So we’ll tackle the inevitable plateaus and setbacks that every PM will likely face at some point in their career – and strategize how to overcome that and come out even stronger. 

Whether you’re an Associate PM just starting or a rising Product Leader looking to make the leap to people leadership, this essay will help you think more deeply about your career in product. 

Let’s dig in…

Understanding the Career Progression

Understanding the Career Progression

One almost certain thing is that there really is no distinct Product Manager career path. In my experience meeting so many product people through our Product Collective community, it seems that almost everybody has a unique path that led them to become a Product Manager – whether it was, at first, starting as a software engineer, customer success manager, entrepreneur, or in countless different ways. That being said, there are some distinct phases that product people tend to go through during their time in product management. Not everybody starts in the first phase, but the phases are Associate/Junior Product Manager, Experienced/Senior Product Manager, and Product Leader. Each phase demands a unique set of skills and mindsets, and mastering them is crucial to unlocking the next level of your career.

Associate/Junior Product Manager: Mastering Execution and Shipping Great Products

Think of this as not a distinct title – but more of a phase in your product management career. In the early days of your PM career, your primary focus is honing your execution skills and learning to ship products that delight users. In this phase, you’ll work closely with cross-functional teams to bring features and products to life, from ideation through launch and iteration.

Jackie Bavaro, co-author of Cracking the PM Career, emphasized the importance of this execution-focused stage in a conversation we had with our community. Bavaro noted that in this phase of one’s career, you may be assigned features for your team to build – and you set out to build those features in the best way possible, using industry best practices. 

But execution isn’t just about ticking off tasks on a project plan. It’s about developing a deep, user-centric mindset and using that empathy to guide your product decisions. Gib Biddle, former VP of Product at Netflix and Chegg, highlighted the importance of “consumer science” in his session with our community on “Hacking Your Product Career.” Biddle contends that good Product Managers and Great Product Managers are separated, at this stage, by being able to dig through the “dirt of the data” and pull out relevant trends when conducting research through qualitative focus groups, surveys, and other ways. 

Mastering execution also means navigating the complex dynamics of stakeholder management and cross-functional collaboration. You’ll need to build strong relationships with your engineering and design counterparts, learn to speak their language and earn their trust through consistent, high-quality delivery.

Perhaps most importantly, this is the stage where you’ll develop your product sense—that intuitive understanding of what makes a great product and how to bring it to life. This product sense will be your north star as you progress through your career, guiding your decisions and setting you apart from your peers.

Senior/Experienced Product Manager: Driving Product Strategy and Winning in the Market

As you prove your ability to ship successful products, you’ll naturally take on more strategic responsibilities. This is where you enter the phase of being a Senior Product Manager. At this stage, you’re not just executing on a given roadmap but defining the direction of your product and how it fits into the larger market landscape.

Bavaro points out that most companies don’t do a good job of explaining how much the job has changed during this phase. So, when you want to move into this phase of being a senior PM, you may have to start independently creating a strategy for your team, your product, or some new product your company doesn’t already do. Regardless of the title on your business card, you’re taking on ownership of being more senior in your role. 

Of course, crafting a product strategy requires a new set of skills and a broader perspective. You’ll need to develop a deep understanding of your market, your competitors, and the larger trends shaping your industry. You’ll need to identify opportunities for growth and innovation and craft compelling product visions that inspire your team and stakeholders.

This work often involves conducting market research, analyzing data to uncover insights, and making tough prioritization decisions based on business impact. As Gib put it, product strategy is about delighting customers in “hard-to-copy, margin-enhancing ways.”

But crafting a winning strategy is only half the battle. As a Senior PM, you’ll also need to develop the leadership skills to rally your team around that strategy and drive its execution. This means honing your communication and influencing skills, learning to manage up and across the organization, and coaching and mentoring junior PMs.

It’s a challenging phase but also an incredibly rewarding one. Seeing your strategy come to life and drive meaningful impact for your users and your business is one of the most fulfilling aspects of the PM role. And it’s the proving ground that will prepare you for the next great career challenge.

Product Leader: Excelling at Organizational Leadership and Building Great Teams

As you progress through the Senior PM phase, you’ll likely reach a fork in the road. Some PMs continue honing their craft as individual contributors, taking on ever-more complex product challenges. But for those who aspire to have a broader impact, some choose the path to Product Leadership – where you move from managing teams to managing people.

Becoming a Product Leader means stepping up to the challenge of organizational leadership. You’re no longer just responsible for your own products but for the success of an entire product organization. This means setting the vision and strategy not just for a single product but for a portfolio of products and the teams that build them.

This is no small feat. It requires a new set of skills and a willingness to let go of the day-to-day product work you’ve honed for years. You must master organizational dynamics, navigate complex stakeholder relationships, and drive alignment across functions and levels.

Biddle points out that product leadership includes necessary cross-functional leadership – bringing together engineering, design, marketing, sales, and other functions to drive toward a common goal. It’s about understanding their needs and perspectives and creating win-win solutions for all stakeholders. As Biddle put it, “The most important thing a Product Leader can do is build a great team. That means hiring people who are smarter than you, giving them the context and resources they need to succeed, and then getting out of their way.”

The Evolving Skills Needed at Each Stage

As you progress through these phases of your PM career, you’ll need to develop various skills and expertise. While the specifics may vary depending on your industry and company, some common patterns emerge.

Early Career: Focus on Core Product Skills

  • Technical skills: While you don’t need to be an engineer, you should have a solid understanding of the technical concepts and constraints that shape your products. It’s less about being able to “code” and more about “speaking the language” of your team.
  • Design skills: PMs need to think like designers, understanding user needs and translating them into elegant, intuitive product experiences. 
  • Consumer science skills: Great PMs are obsessed with understanding their users and using data to guide their decisions. This means developing skills in user research, data analysis, and experimentation.

Mid-Career: Develop Leadership Skills

  • Strategic thinking: Senior PMs need to be able to think strategically about their products and how they fit into the larger market landscape. This means developing skills in market analysis, competitive research, and long-term planning.
  • Management skills: As you take on more responsibility for teams and projects, you must hone your management skills. This includes learning to delegate effectively, provide constructive feedback, and coach and mentor junior PMs.
  • Communication skills: Influencing stakeholders and driving alignment becomes increasingly important as you progress in your career. Senior PMs must communicate complex ideas clearly and persuasively, tailoring their message to different audiences.

Late Career: Master Cross-Functional Leadership

  • Organizational design: Product Leaders need to be able to design and implement organizational structures and processes that enable their teams to work effectively together.
  • Company strategy: Product Leaders need to be able to “influence up” and have a voice in setting and ensuring that the overall company strategy sets the organization up for success. 
  • Industry partnerships: Driving product success often means forging partnerships and alliances beyond the walls of your own company. Product Leaders need to be skilled at identifying and negotiating these strategic relationships.

Developing these skills is a lifelong journey requiring continuous learning and adaptation as product management evolves. But by focusing on the right skills at each stage of your career and seeking out opportunities to practice and hone them, you’ll be well-positioned to navigate the path to Product Leadership.

Strategies for Proactively Advancing Your Career

There are likely many different ways you can proactively advance your career as a product person, but I noticed two key themes emerge in the conversations I’ve had with Gib Biddle and Jackie Bavaro. I thought it was worth focusing on those here… 

Forming Career Hypotheses and Experimenting with Side Projects

One of the most powerful ways to proactively advance your career is to treat it like a product. As you would with a product idea, start by forming hypotheses about what skills, experiences, or roles might help you reach your goals. Then, design experiments to test those hypotheses and see what works.

Gib shared a great example from his own career journey. Early on, he found himself at a fork in the road, unsure whether he wanted to focus on consumer or B2B products. So, he designed an experiment. He took a year off from college and started a sailing school—which, to this day, he credits with introducing him to the consumer world in San Francisco. That experience helped him realize that consumer products were where he wanted to focus.

These experiments don’t have to be as dramatic as taking a year off to start a business. They can be as simple as taking on a side project at work to test out a new skill or domain or volunteering to lead a cross-functional initiative to see how you like the leadership challenge.

The key is to approach these experiments with a learning mindset. 

So, what do successful career experiments look like in practice? Here are a few examples from the product leaders I’ve spoken with:

  • Taking on a stretch assignment in a new domain: Jackie Bavaro shared an example of a PM interested in exploring a career in machine learning. They volunteered to lead a project, collaborating closely with the machine learning team and giving them hands-on experience with the technology and stakeholders involved.
  • Testing out a leadership role: Another PM Jackie worked with was considering transitioning into people management. They asked to take on the role of interim team lead while their manager was on parental leave, giving them a low-risk way to test out the role and see if it was a good fit.
  • Exploring a new industry: Gib shared his experience experimenting with the education industry through a side project. He got involved with an ed-tech startup called Chegg, which led to a significant product leadership role for Gib.

The common thread in these examples is a willingness to step outside your comfort zone and try something new. By designing small, low-risk experiments, you can gain valuable insights about what energizes you and what skills you need to develop to reach the next level.

Having Ongoing Career Conversations with Your Manager

Of course, experimenting with side projects and stretch assignments is just one piece of the career growth puzzle. Equally important is having ongoing, honest conversations with your manager about your goals and aspirations.

1. Articulating Goals and Soliciting Actionable Feedback

One of the biggest mistakes I see PMs make is assuming their manager knows what they want in their career. But as Jackie Bavaro points out, your manager is not a mind reader. You need to be proactive in articulating your goals and asking for the specific support and feedback you need to reach them. This doesn’t mean marching into your manager’s office and demanding a promotion. Instead, focus on having regular, constructive conversations about your career aspirations and what you need to do to get there.

Jackie suggests a simple template for these conversations. It may go something like this:

“I would love to someday become a senior PM (or people manager or product leader). Can you help me understand what I need to focus on right now to be ready when the opportunity comes up?”

By framing the conversation around your long-term goals and enlisting your manager’s support, you can receive more actionable feedback and guidance. Your manager can help you identify the specific skills or experiences you need to develop and connect you with opportunities to build them.

2. Building Trust and Partnership with Your Manager and Their Peers

For these conversations to be truly effective, you need to have a strong foundation of trust and partnership with your manager. This means consistently delivering high-quality work, being receptive to feedback (even when it’s tough to hear), and supporting your manager’s goals and priorities.

In companies where promotion decisions are made by committee, it’s especially important to build connections with your manager’s peers and other leaders in the organization. This doesn’t mean schmoozing or playing politics. It means looking for opportunities to collaborate with other teams, share your work and insights, and demonstrate your value as a partner and leader.

One PM I worked with made a habit of sending monthly update emails to a broad group of stakeholders, sharing the progress and lessons learned from their team’s work. This simple practice helped build visibility and credibility across the organization and opened up new opportunities for collaboration and growth.

The Power of Mentorship and Relationships

The Power of Mentorship and Relationships

As you navigate the ups and downs of your product management career, one of the most valuable resources you can cultivate is a strong network of mentors, advisors, and peers. These relationships can provide guidance, support, and opportunities for growth that you might never find on your own.

Assembling a Personal “Board of Directors”

The concept of a personal “board of directors” has gained popularity in recent years, and for good reason. Just as companies rely on their board for strategic guidance and oversight, product managers can benefit from having a carefully curated group of mentors and advisors to help steer their careers.

Gib Biddle is a big proponent of this approach. He’s openly talked about having a personal Board of Directors his entire career to develop different skills, gain different insights, and access help from people who are “smarter than you.”

So, how do you go about building your own personal board? The key is to be thoughtful and intentional about who you choose to include.

Start by identifying the areas where you need the most guidance and support. You may want to develop your strategic thinking skills or navigate a challenging stakeholder relationship. Look for mentors with deep expertise and a track record of success.

But don’t limit yourself to just one type of mentor. As Gib emphasized, diversity is key. Gib’s personal Board of Directors includes teachers, speakers, authors, and others. It includes past colleagues, current colleagues, and people in different industries and functions. That diversity of perspective is incredibly valuable to Gib. 

When reaching out to potential mentors, start small. Jackie Bavaro points out that you don’t want to just march up to someone and ask them to be your mentor. That can be awkward and intimidating. Instead, look for ways to build the relationship gradually. Start by asking for advice on a specific problem in an email – something that’s easy to respond to and doesn’t require too much time and effort for them to respond. Over time, as you build rapport and demonstrate your value as a mentee, you can explore a more formal mentorship relationship.

To truly maximize the value of these relationships, you need to invest time and effort in maintaining them over time, and it’s important to be respectful of your mentors’ time and boundaries. Some people on Gib’s Board of Directors don’t even know they’re on his Board, but he makes a point of touching base with them regularly, whether every month, every quarter, or every year.

When you do connect with your mentors, come prepared. Have specific questions or challenges you want to discuss and be open to feedback and guidance. But also look for ways to add value back to the relationship. There’s always a way you can create value for your mentors. Maybe it’s sharing an article or resource you think they’d find interesting or making an introduction to someone in your network.

Don’t be afraid to evolve your board over time. As your goals and needs change, so too should the composition of your board. Be proactive in seeking new mentors and advisors who can help you tackle the challenges of each new career stage.

Investing in Peer Relationships and Building a Strong Network

While mentor relationships can be incredibly valuable, don’t underestimate the power of peer connections. Some of the most meaningful relationships in your career may be with people who are at a similar stage of their journey.

For many people, the word “networking” conjures up images of awkward happy hours and transactional business card exchanges. But networking doesn’t have to be a dirty word. At its core, it’s about building genuine relationships with people who share your interests and values. One of the best ways to build these relationships is to show up and be helpful. Look for opportunities to connect with peers in your industry or function through professional associations, conferences (like INDUSTRY: The Product Conference), or online communities (like Product Collective). When you meet someone new, focus on getting to know them as a person, not just as a potential job lead or reference.

Over time, these relationships can blossom into genuine friendships. Some of my closest friends today are people I met early in my career when we were all just starting in product management. We’ve supported each other through job changes, product launches, and personal milestones, and those relationships are just as valuable to me as any mentor or advisor.

Of course, building and maintaining these relationships takes time and effort. But investing in relationships is one of the most important things you can do for your career. Those relationships will sustain you through the ups and downs and open up opportunities you never could have imagined.

Learning from Failures and Plateaus

Learning from Failures and Plateaus

No product management career is a smooth, uninterrupted ascent to the top. Along the way, you’ll inevitably encounter failures, setbacks, and periods where you feel like you’ve plateaued. These moments can be frustrating, demoralizing, and even scary.

But as I’ve learned from countless conversations with product leaders, these challenges can also be some of the most valuable opportunities for growth and learning in your career. The key is to approach them with the right mindset and strategies.

One of the most common challenges product managers face is feeling like they’ve hit a plateau. Maybe you’ve been in the same role for a few years and feel like you’re no longer learning or growing. Or you’ve been passed over for a promotion and wonder what you need to do differently.

Recognizing when you’ve plateaued is the first step to breaking through. Getting comfortable in a role is easy, especially if you’re good at it. But if you find yourself doing the same things over and over again without feeling challenged or energized, that may be a sign that it’s time for a change.

So, how do you break through a plateau? A few strategies come to mind:

  1. Seek new challenges: Look for opportunities to take on new projects or roles that stretch your skills and push you outside your comfort zone. As Gib put it, “Growth happens when you’re uncomfortable.”
  2. Invest in your learning: Use resources like books, courses, and conferences to deepen your knowledge and expand your perspective. Continuous learning is essential to staying relevant and valuable in a rapidly evolving field.
  3. Get feedback from trusted advisors: Sometimes, it takes an outside perspective to help you see where you need to grow. Seek honest feedback from your manager, mentors, and peers on where you excel and where you have room for improvement.
  4. Be willing to make a move: Sometimes, breaking through a plateau may require a bigger change, like switching teams, companies, or even industries. Don’t be afraid to explore new opportunities if you feel like you’ve hit a wall in your current role.

Sometimes, a more personal setback – such as a layoff – can feel even more emotionally disconcerting. A layoff does not have to define you, though. Remember that nearly everybody experiences a layoff at some point in their career. It’s not a reflection of your inherent value as a person or professional. 

But how do you bounce back?

  1. Give yourself time to process: Feeling angry, sad, or frustrated after a setback is okay. Permit yourself to process those emotions rather than trying to push them aside or pretend they don’t exist.
  2. Seek support from your network: Lean on your mentors, friends, and family for emotional support and practical advice. They can help you gain perspective, identify new opportunities, and remind you of your strengths and values.
  3. Reflect on what you can learn: Once you’ve had time to process, try to extract any lessons or insights from the experience. Were there skills you needed to develop, relationships to manage differently, or priorities to rebalance?
  4. Reframe the narrative: Getting caught up in negative self-talk after a setback is easy. But try to reframe the experience in a more positive light. Instead of “I failed,” try “I learned something valuable.” Instead of “I got laid off,” try “I have an opportunity to explore new possibilities.”
  5. Take action: Finally, don’t let a setback paralyze you. Look for small, concrete steps to move forward, whether updating your resume, reaching out to your network, or exploring new learning opportunities.

Remember, setbacks and failures are not the end of your product management journey. They’re simply part of the terrain you’ll navigate on your way to success. By approaching them with a growth mindset, a willingness to learn, and a commitment to resilience, you’ll come out stronger and better equipped for the challenges ahead.

Summing it all up

Navigating your product management career path is a journey filled with twists, turns, and unexpected detours. It requires a unique blend of skills, mindsets, and strategies at each stage of the game.

But career growth isn’t just about acquiring technical skills or climbing the corporate ladder. It’s about building meaningful relationships with mentors, peers, and cross-functional partners. It’s about having the courage to experiment, to take risks, and to learn from failures. And it’s about staying true to your passion for building great products that solve real user needs.

As you navigate your product management journey, remember that setbacks and plateaus are inevitable. But with the right strategies, support system, and mindset, these challenges can become powerful catalysts for growth and transformation.

So embrace the journey, with all its ups and downs. Stay resilient, keep learning, and, as the great Ted Lasso says, be curious, not judgmental. 


Mike Belsito

About the author

Mike Belsito is a startup product and business developer who loves creating something from nothing. Mike is the Co-Founder of Product Collective which organizes INDUSTRY, one of the largest product management summits anywhere in the world. For his leadership at Product Collective, Mike was named one of the Top 40 influencers in the field of Product Management. Mike also serves as a Faculty member of Case Western Reserve University in the department of Design and Innovation, and is Co-Host of one of the top startup podcasts online, Rocketship.FM. Prior to Product Collective, Mike spent the past 12 years in startup companies as an early employee, Co-Founder, and Executive. Mike's businesses and products have been featured in national media outlets such as the New York Times, The Atlantic, CNN, NPR, and elsewhere. Mike is also the Author of Startup Seed Funding for the Rest of us, one of the top startup books on Amazon.


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