Episode 43: What We’ve Learned from CPOs so Far

Before we hear more from our guests and their #PathtoCPO, reflect on the past episodes of this podcast series with Rashmi Ramesh, Director of Product. We wanted this series to inspire our community members to pursue executive roles, and we hope you are encouraged by the stories our guests have shared. Listen to the top takeaways from the different speakers and consider how you can apply them to your career.


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Reflections on Paving Your Path to Chief Product Officer


By: Evelyn Chou, Senior Product Manager, Coursera

Just like moons and like suns,

With the certainty of tides,

Just like hopes springing high,

Still I’ll rise.” ~ Maya Angelou, Still I Rise


What is your first reaction when you hear the title “chief product officer” (CPO)? Have you decided that is where you will be one day? Or are you still unsure whether that’s the destiny you should strive for?

Having been in the Women In Product community for about five years, I am occasionally tempted by the idea of joining the executive realm, but the path to getting there feels unattainable. Yes, I have built teams from the ground up. Yes, I have managed complex initiatives and delivered impressive business results. But the thoughts of perpetually playing politics, maneuvering investors and board members, and betting on a company that would use my strengths still seems daunting. What do we have to give up to climb to CPO?

Nupur’s compelling story and frank reveal of what got her to where she is now are illuminating and a wake-up call.

Nupur Srivastava is currently the CPO at Included Health. Having worked at other healthcare organizations such as AliveCo, Maternova, and Grand Round Health, Nupur joined Included health as a senior product manager. Within 9 years, she was promoted to Director, VP, SVP, and then her current role. Nupur distilled her journey into these following principles:

Anchor to present learning opportunities

When asked whether she thought that she would become a CPO one day, Nupur admitted that was not something she deliberated on initially, but she has always had a track record showing her growth trajectory. “As long as I keep delivering impact, I know I would eventually grow at the pace that matches my goal. People learn in respect to their environments.” To some, the race to the top is like a music chair. People switch companies to get higher titles or better salaries, and it’s invigorating to hear Nupur honing in on the fundamentals by meticulously connecting to the company strategy while deeply empathizing with her customers. Focusing on what she has at hand and nailing what she owns are Nupur’s superpowers.

Reframe professional sacrifices as intentional choices

Nupur explained in detail some of the intricacies of the healthcare industry—the dynamics between peers (insurance companies) and users (patients or members), the emphasis on privacy around personal health information, and compliance with strict regulatory requirements. When asked what kinds of sacrifices she had to make in her career, Nupur said, “the decisions I’ve made are oriented around having an impact for the world. Having that clarity makes the decision more of a conscious choice than a sacrifice. I tend to work a lot, but actions are more fun because they align with my value. And once it’s a conscious choice, you just have to deal with the consequences.”

Rethink leadership principles

Nupur’s passion for people and teams is palpable throughout the interview. She mentioned two books I can’t wait to dive into: The 5 Dysfunctional of a Team and The Ideal Team Player, both by Patrick Lencioni. One application is to invest time hiring the right people—those who are hungry (for impact), humble (no big egos), and smart (emotional intelligence). Another way is to hire for diversity so that collectively a product organization has diverse thoughts; therefore, it’s poised to service different types of customers. Nupur’s advice to first-time people-managers about the concept of a first-team is deliberate. While many new managers mistake the job of a manager as fighting and protecting the team, Nupur learned early on that the more a leader can consider her first team as her peers, the more she can optimize for the company, and the better off the team will be.

As I reflect on Nupur’s journey, I am reminded of other women in the product space who have blazed similar trails. This includes leaders like Alex Hardiman at the New York Times (episode 37) and Anneka Gupta at Robrik (episode 38). These women inspire us to push ourselves further and stretch for our goals, no matter how out of reach they may seem.

The truth is, the paths to executive leadership can feel like uphill battles, especially for women and other underrepresented groups. But Nupur’s story reminds us that with perseverance, a growth mindset, and a commitment to learning, we can ascend the peaks of our professions and positively impact the world.

If you’re still unsure whether you have what it takes to become a CPO, take a cue from Nupur and other inspiring women like her. Anchor yourself in the present, reframe professional sacrifices as intentional choices, and rethink your leadership principles. And remember, with hard work and dedication, the impossible can become possible.

Listen Now

Evelyn will be speaking at the 2023 Women In Product Conference on Navigating Reorgs. She’ll walk through the process of gathering information in two categories during organizational turmoil, and you’ll use a 2×2 matrix to assess your knowledge and awareness of the reorg.


About the author

Christine Lee


Christine Lee is a Senior Director of Product at GoDaddy, where she leads the team building DIY products for entrepreneurs to grow their business online. She loves supporting the Women In Product community as a Board Director and co-founder. Previous roles have spanned consumer, small business, and enterprise software at Twitter, Intuit, Oracle, and Hired. Christine holds an MBA from Wharton and a BA from Duke University. Outside of work, she enjoys making desserts, crafting, and attempting DIY home improvements.


Build Your CPO Persona Profile

How Experimentation and Pivoting in Your Career Makes You a Stronger Executive

By Jenna Gaudio, Co-President at Vydia

Jenna Gaudio listened to our podcast episode with Jen Taylor of Cloudfare and these are her takeaways.

The path from product manager to executive is usually a winding, unpaved road without any clear signs or guides to make sure you’re headed in the right direction — especially for women. Sometimes if feels like I had to learn every lesson the hard way on my journey to VP Product Management, Chief Operating Officer, and now Co-President of Vydia.

Listening to Jen Taylor, Chief Product Officer at Cloudflare on the Women In Product podcast provided me the insightful comfort that my own experience is not that uncommon. Hearing Taylor unpack the lessons that shaped her perspective resonated with me deeply, validating that growth is not linear and it is also never-ending.

Jen Taylor, The Path to CPO

Taylor takes us through her early career experimentation and attributes her agility to landing where she has today. I appreciated how she spoke about trying different roles and working for different types of companies, which allowed her to more confidently calibrate who she was as a leader.

I like to call this the process of building your own Executive persona profile.

Taylor walks us through the discovery process required of arriving at the right role at the right company. This requires asking questions such as:

  • Do you thrive best in the B2C or B2B space?
  • Do you best collaborate with technical or visionary founders?
  • Are you energized by talking with clients or internal teams?
  • What is the chemistry of the existing executive team and how do you fill the gaps?
  • What is the vision and are you aligned?

When talking about challenges, Taylor advises that you should be prepared to take on complexity, scope, and responsibility outside of your core domain expertise.

How do you prepare for this?

She shares something I tell all my mentees — you almost always have to do the work before the title and be willing to take the risk. Also, the unspoken secret is that there is no manual for how to become an executive and do the job well. This is why it is so critical that you start building a supportive community and network of executives right now. This will be your place to turn to ask the tough questions or just compare notes on how do YOU lead as CPO?

The challenges she touches on are areas where I often see people get caught up as well. A few career moments to focus on overcoming may include:

  • The transition from IC to a Manager. She walks through the importance of learning the skillsets of people you’ll manage (i.e. Design, Tech, Marketing, etc) so you’ll have that as a foundation and become a good communicator and coach to your future team.
  • Learning to make decisions without all the information.
  • Being able to work with diverse perspectives and productively disagree.

Where will you spend most of your time being an impactful executive?

Taylor and I both agree on the investment of architecting and scaling a team is where you spend a lot of your time. The payoff is enormous though. Not only will this dictate the success of your company, but these are the people you will learn from as much as they will learn from you. Be vigilant in hiring the right people. Your company culture and the success of your product depend on it.

Join the Women In Product Facebook Group to be a part of the conversation.

About the author

Jenna Gaudio, Co-President, Vydia


Jenna Gaudio is a media technology executive who specializes in building, aligning, and scaling successful teams that deliver industry-leading outcomes. Gaudio now serves as the Co-President (previously COO and VP Product management) at Vydia, a media technology company that has recently been acquired by media mogul Larry Jackson’s, gamma. Prior to Vydia, Gaudio also played an integral role in the successful exit of early-stage Ad Tech startup, Yashi, which was acquired by Nextstar Media Group in 2015.

There’s No Linear Path To Becoming A Chief Product Officer

Anneka Guptas’s Path to Chief Product Officer

By Becca Camp (she/her), Executive Coach and Founder of the Fearless Femmes

Becca Camp listened to our episode with Anneka Gupta of Rubrik.

Becca’s Takeaways

As a product leader-turned-entrepreneur, I occasionally think about what Cheryl Strayed calls “the ghost ship that never carried me”—that weird parallel timeline where one little thing went different, one hesitation, one choice–and I ended up as a CPO, instead of founding and running my own business.

It’s definitely not a feeling of regret–I’m obsessed with what I’ve created, and it’s perfect for me. But it tickles me to imagine what would have needed to happen to arrive at CPO.

So naturally, every time I meet a CPO–whether it’s one of my clients, a friend, or listening to an interview like Anneka’s–it’s a jolt to hear just how similar our timelines already are.

Anneka Gupta, The Path to CPO

My path was “non-traditional” and “non-linear” and I made moves “based on intuition and what I was most curious to learn”. I invested heavily in community because it’s been my superpower since before I had language to describe it–leaning on authentic relationships to support me in my success. What I studied in college somehow has both nothing AND everything to do with my day to day now.

So, pretty much all paraphrases Anneka used to describe her own rise to CPO. How can she and I seem so different in our titles, yet also so alike?

I’ll zoom out: the BIG takeaway from this episode is that there’s simply no such thing as a linear path.

We’d do well to release the hope that there’s just a template or blueprint to study, like if we check the boxes and get the A+, we’ll end up with the “right” title. In this episode, you’ll love how Anneka describes channeling her innate interest in something, and letting it guide where she invested her time.

While we’re at it, one term I wish we could retire from work-speak is the “career ladder”. I think everyone is way over this idea of “getting to the top” for its own sake; the future of work has real soul, and we won’t tolerate anything less.

I prefer the term career playground–and I hope you feel inspired by Anneka’s playful and flexible approach to her career path.

My calling has always been community-building–and I find that whether someone admits it or not, leaning on the people around you for inspiration, support, guidance, and sponsorship is the #1 factor in whether someone accomplishes their goals of rising professionally.

I believe in this so much that I invented a full-time job out of it, so it’s a pattern I look for anytime I listen to someone’s story.

Anneka alludes to community several times in her interview: she got recruited into the CPO role (that happens when people know you); she was given access to coaching early in her career; she was offered opportunities to work with the board during her tenure at LiveRamp before making the leap to Rubrik, and had excellent CEOs to mentor her throughout her career.

She was able to use this access and support to expand into the shape of CPO: quite different from VP, as her job in the C-suite is more heavily a synthesizer role–or, as Anneka puts it, “You have to kind of take all of their approaches, their ideas, their concerns for what is it going to take to get there, and really meld that into a plan that everyone can get behind.”

This is consistent with my work with VPs and CPOs in my coaching business.

At the VP level, we see an emphasis on advocating for your team, getting them the resources they need, and enabling great work by whatever means necessary while keeping the team focused on what’s most important. You are an essential conduit of information between the C-Suite and your Directors.

The CPO role, by contrast, has a major element of being the “handler” of other members of the C-Suite. The strong personalities, opinions, and idiosyncrasies that made everyone so successful as individuals often become points of friction at the highest level.

Thus, a lot of time in the CPO role is spent managing personalities (one’s own, included) so the whole business doesn’t go sideways.

The only way to cultivate this skill is to get your hands dirty in your community (inside and outside work) and build a toolkit (usually an emotional and relational one) to self-manage and dive into the messiness of human leadership. Embrace it. Learn to love it.

The CPO role is not for everyone–but not because you aren’t competent; you just have to love the mess. That’s ok if you don’t. I didn’t either! Working as the only executive at a company of my own creation has been a great joy of my life. Anneka, by contrast, seems to love it on a fundamental level.

Though Anneka and I have similarities in our paths, we ended up in totally different executive leadership roles.

Starting with how you want to spend your time–like, literally, the kinds of events that appear on your calendar all week and who’s involved in them–should be the starting point for anyone considering an executive track role.

In fact, most product roles that are similar in title are wildly different in scope, responsibilities, and expectations of how you’ll allocate your time.

Every team has a unique product-shaped puzzle piece slot, waiting for someone with complementary skills, traits, and desires.

Just as you have a unique job-shaped puzzle piece slot, waiting for a role that complements it.

Anneka built a track record of putting her team first, finding the most genuine pleasure in cultivating talent and leadership within people who worked with her. It’s no accident that she arrived at CPO as quickly as she did. If you don’t connect with the hearts of your people, it’s very difficult to lead them. I love highlighting this squishy human–or, as Anneka put it, “complicated” element of professional success.

This episode narrates a beautiful combination of skill, hard work, willingness to jump on opportunities, and luck that gave Anneka access to what I see as the most essential ingredient to her rise to CPO: her relationships, which she proceeded to put years of dedication and energy into.

For those of you unsure if a CPO title is your destination–take heart. It doesn’t have to be the end game, for your journey to be delicious, fabulous, and full of learning. Follow Anneka’s advice to stay curious, be honest with yourself, take life as it comes, trust yourself, and surround yourself with people you’d want to be. You’ll end up in the right place.

Questions for reflection:

What is the shape of your “puzzle piece”? I like breaking it down simply, into three points:

  • Your 1-2 primary skills/areas of expertise
  • Your 1-2 activities you LOVE even if you aren’t an expert
  • The 1-2 skills you are super excited to build next

In some ways, it doesn’t matter what title you have; if a role fits your puzzle piece, you will be fulfilled, delighted, and valued. And if it doesn’t fit, it will be hard to feel those things.

  • What is one thing about you that you’re scared to “own”? For me, it’s how intense my emotions are / how sensitive I am. Whatever it is for you, I can basically guarantee it’s actually your superpower. Start playing with sharing this part of yourself with others.
  • What are some ways you are living into your value of community these days? Can you come up with three? What might be an opportunity to lean more into it, given its power as a career engine?

Join the Women In Product Facebook Group to be a part of the conversation.

About the author

Becca Camp


Becca’s a former product leader who pivoted to build a multi-six-figure business working as a product consultant and coach. She’s on fire with the mission to reinvent work culture by getting women promoted to leadership roles, and/or break free to build a successful business of their own.

After driving product initiatives at several startups, she found her true calling being her own boss, defining work on her own terms, and being of service to femmes in product who want to put the soul back in their careers.