Tech Icon Spotlight:
Anneka Gupta
Chief Product Officer, Rubrik
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Anneka Gupta likes to say she has tech in her blood. “Both my parents were Indian immigrants who each ended up founding their own companies and taking them public,” she said. “Our dinnertime conversation was always about what was happening in the tech industry or their businesses.”
That early exposure to innovation shaped the way Gupta thinks about building products and leading teams. Now as Chief Product Officer at Rubrik, she applies her technical fluency, strategic thinking, and cross-functional leadership to help scale one of the world’s most innovative data security companies. To learn more about her approach, Riviera Partners asked Gupta to share her insights into product leadership, adapting to emerging technologies like AI, and building teams rooted in authenticity, curiosity, and trust.
Working at the intersection of everything
Gupta was drawn to product management early in her career due to the sheer breadth of what the role demanded.
“At my first job after graduation, I enjoyed seeing what the VP of Product was doing, and how the job he had sat at the intersection between the technology, sales, and the customer,” Gupta said. “On any given day, I can be having a call with a customer, in an internal strategy discussion, looking at finance business metrics for a particular product, or leading an all-hands. There’s so much variety, which keeps me excited and interested.”
Gupta said that the key to product leadership is recognizing that building a product is fundamentally about building the business. This means constantly reevaluating where to spend time and resources so that you focus on the company’s success, not just what is technically interesting.
“You have to know what the biggest opportunities and risks are at any given moment,” she said. “Every decision is about setting the business up to win in the future, because anything we build today won’t be fully monetized for at least a year or so.”
Every decision is about setting the business up to win in the future, because anything we build today won’t be fully monetized for at least a year or so.”
Adapting at the pace of AI
AI is evolving faster than product roadmaps can keep up. By the time you identify customer demand or start sketching out a new product, it may already be too late.
“Look back at how businesses dealt with the cloud. There was time to learn where customers were in terms of their adoption of cloud and the hurdles they were facing. It was much more customer-focused because the technology wasn’t moving so fast,” Gupta said.
“Whereas with AI, things are changing so fast month to month, and experts have radically different views about where it is going. We can’t totally change our product strategy on a dime just because of some new AI technology, but we also don’t want to move too slow. As a product leader, you have to have a strong finger on the pulse, be constantly learning and testing hypotheses of where value is going to be created in AI. But it never feels fast enough. I think everyone I talk to about AI is like, ‘Oh, I feel so behind.’”
For product leaders, AI creates new opportunities to lead customers instead of responding to demand.
“I can imagine the future that might happen within a large enterprise much more easily than customers who are focused on their day jobs,” she said. “In that way, it’s pretty exciting because if some of these trends manifest the way we think they’re going to happen, it opens up entirely new ways to better serve customers.”
I think everyone I talk to about AI is like, ‘Oh, I feel so behind.’”
Leading with authenticity and self-awareness
Growing up in Silicon Valley, the archetype of leadership Gupta saw celebrated was the hard-driving, visionary founder with audacious ideas but a lack of EQ. “I thought that was the only version of leadership,” she said. “And I remember thinking, ‘Well, that’s not me.’”
She’s since discovered that leadership can take many forms, and that the right approach is the one that is authentic to you. “For me, that means I have to be passionate, excited, and transparent. I want people to feel that I am approachable enough to bring ideas or raise concerns, especially if they disagree with the direction we’re going. That kind of culture makes us stronger.”
But finding your leadership style also depends on cultural fit. “Different companies reward different kinds of leadership,” she said. “At Rubrik, you have to be able to operate strategically and also roll up your sleeves and dive into the details. That’s how I like to lead, so it works. But that kind of leadership doesn’t work everywhere, and it doesn’t work for everyone. It’s really hard to be a good leader if you don’t have the self-awareness of what kind of leadership you bring to the table and how that matches with the expectations of the particular company you are in.”
It’s really hard to be a good leader if you don’t have the self-awareness of what kind of leadership you bring to the table.”
Asking the right questions to find better leaders
When interviewing potential leadership hires, Gupta looks beyond resumes and portfolios to explore whether they’re capable of leading people, not just shipping features.
“I try to ask them questions that help me understand the degree of self-awareness they have about themselves,” she said. “That’s not something I can teach. I can help someone work through a blind spot if they’re self-aware, but if that awareness isn’t there, it’s a much harder path.”
Instead of asking about strengths and weaknesses, Gupta goes deeper. “One question I like to ask is: what has been the most difficult point in your career? If someone’s willing to be vulnerable and really go there, the whole tone of the conversation shifts.”
She also wants to understand what drives or drains them. “I’ll ask them to pull up their calendar and tell me: what are the meetings that give you energy? What are the ones that sap your energy? It’s a good way to understand motivation.”
When it comes to assessing emotional intelligence, she asked questions to uncover their approach to feedback. “I’ll ask about what’s the most difficult piece of feedback they’ve received in the past couple of years from a peer, a manager, a direct report, or even a customer. Then I dig into how they responded. Did they reflect on it deeply? Did they challenge it? Did they discard it without thinking?”
I can help someone work through a blind spot if they’re self-aware, but if that awareness isn’t there, it’s a much harder path.”
About Riviera Partners
Riviera Partners is a global executive search firm specializing in placing top talent in cybersecurity, AI, data, engineering, product management, and more. With a focus on understanding the unique needs of tech companies, we match organizations with leaders who can drive innovation and security in today’s rapidly evolving digital landscape. Contact us here.
