Episode 38: Anneka Gupta, Chief Product Officer, Rubrik

The Path to CPO

Director of Product, Rashmi Ramesh, talks with Chief Product Officer, Anneka Gupta, about her #PathtoCPO, the importance of building connections, the art of asking for help and the most important lessons she’s learned as a people leader.


Related Episodes

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.

Balance, Boundaries & Productivity

How to Work Smarter Remotely, Without the Mental Toll

By Heather Inocencio, CEO & Co-Founder, The Product Consult & Jessica Nelson Kohel, COO & Co-Founder, The Product Consult

Wellness. Balance. Mental health. Self-care. People-first. These are some of the terms that have become increasingly common in the last 5-10 years when companies talk about their culture, values & work style. On the one hand, it is refreshing. But is it really true? And how do we ensure that we care for others and their well-being without sacrificing the efficiency, productivity, and outcomes that our teams deliver?

One thing that cannot be disputed is that things have changed significantly in the last 10+ years within the product & tech industry and how we operate. Together, in our combined 50 years of product management experience, we’ve seen a tech boom, a recession (or 2 or 3?), years of 60+ hour work weeks (the hustle), a shift towards remote work culture, and most recently a pandemic that changed nearly everything about how, where, and when we work.

Remote work and productivity: first, fewer distractions meant an increase in focus and output.

Jessica: When I first started working remotely over ten years ago, there was a learning curve. I had a couple of months where I had to figure out my routine, my office setup, and how to balance the temptation to do chores at home with being productive and focused on my work. The tools we’ve become accustomed to today weren’t used as widely, and things were a bit clunkier at times.

Heather: I’ve been working with remote teams my entire career. I love that we can enjoy this flexibility, but I also found that I didn’t know how to “turn it off.” When working remotely, I can easily pull far longer days than I should. The blur between work life and personal life is exacerbated by having my office in my home (or my dining room or my bedroom…). I’ve found it helpful to have my “office” set up in its discreet spot so that, at the [healthy] end of my work day, I can close my laptop and create that sense of moving into a new stage of the evening.

Jessica: At first, I very much missed in-person socialization, camaraderie, and collaboration. But then it shifted. I realized I could get exponentially more done at home with fewer distractions – going out to lunch, chatting in the lobby with coworkers for 10 minutes here and there, people stopping by my desk, etc. While all of that can add positive aspects to my day, ultimately, I was able to get the same amount of work (or more) done in much less time without those distractions.

Next, we realized that, eventually, we were much less stressed out.

Jessica: I did not have to deal with commuting, traffic, parking, rushing out the door, or worrying about what to wear to work every day (we all know it can be a struggle). I could throw in some laundry between meetings, make a healthy lunch or snack when hungry, take the dogs on a short walk and get some fresh air, etc. Those small, simple things alleviated the amount of work I would come home to each day or the chores that would stack up on the weekends. Just to be clear, I am not advocating using the work-from-home time to spend 4 hours deep cleaning the house in lieu of working, but these small adjustments allowed me to feel a bit happier, less stressed out, and made me much more productive as a whole.

Heather: While I enjoy the heads-down time to get work done, I love collaborating. I am so happy to see the widespread acceptance and use of video calls. Being “present” on the calls is key. It’s no fun seeing someone else typing, looking at their phone, etc, when on a video call. So really focusing on the other person/people, making eye contact (as much as you can), and using non-verbal cues like nodding, smiling, etc., all go a long way in building that feeling of connectedness.

Jessica: I also saw the concept of ‘work smarter, not harder’ in action. When spending all of my days in the office, it just was not the most efficient way to operate. It was harder to have focused, heads-down time. I was constantly in meetings. I was interrupted on a regular basis if I sat at my desk. None of that was an issue when I switched to hybrid or fully remote work. Even with a heavy meeting schedule, I could do uninterrupted work at a faster and more productive pace. I was also able to more easily collaborate with team members in different time zones and different countries (for example, morning standups with an offshore dev team at 7 AM didn’t feel nearly as burdensome when I could take them from home and not have to race to the office afterward).

Finally, being remote meant that not everything had to be squeezed into normal working hours if it was asynchronous or independent work.

Jessica: I could structure my days a bit more flexibly, ensuring that I was delivering on professional priorities and taking care of myself in small ways. So when exceptions arose, like an important product launch at 11 PM on a Tuesday (we’ve all been there, right?), I didn’t feel quite as exhausted or burnt out. The decrease in my mental load in these areas alone made a big impact. I was able to find a balance that worked well for me, for my colleagues, and that ultimately enabled me to create more of the lifestyle I wanted and needed.

Heather: The important thing here is to be fully present during the collaborative time and balance general online availability with healthy boundary setting. Because we miss those small moments of in-person interaction, it takes more effort to build relationships and trust, so even small things matter. During meetings, I prefer to see people with cameras on (at least most of the time) and do so myself.

Work-life balance and mental health

Jessica: Now, enter children and Covid. I’m sure countless other working parents can identify with a myriad of feelings and challenges that come with one of those life changes, let alone both. Working from home during a pandemic with young children (and anxiety, concern about world events, cabin fever, and an endless list of other emotions during 2020) was a special kind of challenge. Simply put, it was really, really hard. And I was lucky enough to be in a position where I had a supportive partner and family nearby. Many others were not nearly as fortunate, and I very much acknowledge the privilege in my circumstances.

“The ‘good’ news is that the vast majority of other working parents found themselves in similar situations with no childcare, balancing work with kids at home, and no help due to quarantine.”

Jessica: It was hard to balance, to say the least. But something else changed significantly during that time. Remember the videos that circulated online — someone doing an interview with CNN and attempting to stay focused while their toddler enters the room behind them and starts getting into everything, the attorney who turned his Zoom filter into a cat, parents with kids on their laps during important work meetings, etc. Companies and people, in general, became a bit more understanding, a touch more relaxed, and a lot more empathetic because no one was immune to this challenge in some form.

As parents, professionals, and human beings, all susceptible to the pandemic and every challenge that came with it, we all had to stop for a moment (or, in some cases, repeatedly) and rethink our priorities. We had to ask ourselves what mattered in life and how we were going to stay healthy and sane, balancing all of the challenges and constant new information.

While it was in no way easy, one of the small silver linings to emerge from it was this shift in understanding about how we work, how we support each other, and what matters most.”

Jessica: Yes, the products we are building and the companies we are helping are hugely important, but if we don’t have our basic mental health, it’s near impossible to do anything else well. Placing more value on how we care for ourselves and others is essential and ultimately should impact the companies we work for in a very positive way. If I took nothing else from the first few months of Covid, that sentiment was enough.

As a result of all of this, when we started our first company in early 2021, the first thing we did was establish core values. How do we want to show up as a company? How do we want to build a culture that focuses on our people and their well-being? And how do we not just talk the talk but walk the walk? How do we create healthy boundaries and ensure that people do great work and don’t take advantage of the culture? Hint: honesty and integrity are some of our core values.

Creating boundaries in a leadership role

“It starts with how we show up, both as humans and as leaders. Speaking from experience, it’s hard to create healthy boundaries if you don’t see your leaders doing this for themselves.” 

Jessica: That hustle culture we all became accustomed to in tech in the 2000s was a not-too-distant memory. I remember thinking, ‘It’s 6 PM, but I shouldn’t leave the office yet because look at everyone that’s still here, including all of our bosses.’ Or ‘I got here at 7:30 am today but look at everyone that was here earlier; I should come at 7 am tomorrow, or people might think I’m not as dedicated or valuable.’ Or ‘Another happy hour? I really need to get things done at home, but I don’t want anyone to think I’m not committed to this team and this company if I don’t go.’ All of that exists more when in-person vs. remote, but it also starts at the top.

Heather: What Jessica describes here can happen when working with remote teams as well. It just changes to “who is the first on Slack in the morning and who is still on when I’m signing off”. Being logged on to Slack has replaced being in your seat at the office. One way to combat this is to openly discuss with your teams, employers, peers, etc., the need for healthy boundary setting and that just because you aren’t logged on doesn’t mean you’re not working. I’ve started using the Focus feature on my Mac to turn on notifications, and I chose the setting that lets them know I’m in focus mode. I also sometimes just completely log out of Slack so that I’m not tempted to click that little icon at the bottom of my screen.

Jessica: If our teams see us consistently say one thing but do another, they will not feel confident in enforcing their own boundaries or in living by the values we said we support as a company. They will feel pressure and stress to check Slack after hours, reply to emails at 10 pm, or work weekends. It’s hard to shed the hustle culture mentality if we don’t feel supported in doing it or see positive examples of how it’s done. Setting healthy boundaries can and should create happier, healthier, and more productive teams — who then deliver better work as a result. It’s a win-win.

Heather: I am learning to use the send-later feature more and more on both Slack and email. I try to strike the balance there, though, as I don’t want anyone suddenly getting inundated with messages from me, so I’ll stagger the times that they send. I also keep a local running list of items for each person that I work with. This way, when we speak, I can cover the important topics.

Jessica: We’d be remiss if we didn’t call out that this is hard to do, and the experience may vary greatly for people. It also will not always be a straight line or path, and there will be exceptions, times when we need/want to hustle or go outside of our boundaries. Gender, race, age, and other factors may impact a person’s comfort level in setting boundaries out of fear that it may negatively impact them due to any number of biases unrelated to their job performance. It’s important to keep these differences in mind, learn how to be better partners and colleagues, and increase focus and action on all things DE&I.

“It is all of our jobs to support, encourage, and communicate that our values apply to everyone on our team equally.” 

As colleagues, it is imperative that we treat each other with respect and compassion. As leaders, it is imperative that we not only talk openly about these challenges but provide the resources, support, and care required to ensure that our teams feel comfortable, empowered, and able to advocate for themselves and their boundaries at work. We will all be better for it as a result.

Heather: I always encourage my teams to “have each other’s back” and “when in doubt, give each other the benefit of the doubt.” It goes a long way in building trust, teamwork, and sanity and lowering stress in general.

Health and well-being in the workplace will continue to evolve, hustle culture will still exist, and the debate about returning to the office vs. staying remote continues for many companies. We may not have control over those things at a macro level, but if sharing these learnings can help even one product manager, leader, or individual feel empowered or better equipped to set healthy boundaries, it’s worth it. In the tech industry, we are used to rapid iteration, but we don’t always apply those learnings to ourselves or our own needs. Let’s take what we learn, use it for good, and hopefully, we can all show up better as a result.

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About the authors

Elizabeth Ames
Jessica Nelson Kohel

Heather Inocencio (top) & Jessica Nelson Kohel (bottom)

Heather & Jessica have been colleagues for over 15 years and are now co-founders of The Product Consult, a boutique consulting firm focused on bringing digital product management expertise to companies in a more flexible, value-driven way.

Their experience spans early-stage startups through enterprise companies in a variety of industries & verticals. Their core focus is on providing a supportive, balanced, and enjoyable work culture that puts people first and delivers exceptional product management support to clients.