Episode 37: Alexandra Hardiman, Chief Product Officer, The New York Times

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.

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.

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