OpenTable Product SVP on The Three Things Great PMs Have That You Cannot Coach

What separates a good product manager from a great one, and can you actually spot it in an interview? In this episode of the CPO Rising Series hosted by Axiom Law CPO Katrina Benjamin, OpenTable SVP of Product Shayani Roy speaks on the three things great PMs have that you cannot coach, why the CPO role is fundamentally shifting from people management to doing, and what it means to build products for an industry as creative and relationship-driven as restaurants. With 60,000 restaurants and 1.9 billion diners annually, OpenTable’s approach to AI, velocity, and innovation offers a masterclass in how to move fast without losing focus.

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Show Notes:

1. The CPO role is shifting from pure people management to doing. The expectation that great leaders inspire and delegate while others execute is changing at every layer of management. The leaders who thrive now are the ones who can both lead and build.
2. There are three qualities that consistently separate good product managers from great ones: proactivity, curiosity, and resilience. These are incredibly hard to coach, and if you hire someone who genuinely has all three, they tend to move mountains regardless of what domain they are working in.
3. Proactivity means a bias for action, not waiting for permission. The question in an interview is not whether someone can describe initiative. It is whether you can find multiple concrete examples of them going a step further without being asked. That pattern is either there or it is not.
4. Curiosity is rarer than people assume. In a world where the competitive landscape, the technology, and customer expectations are all shifting rapidly, hiring people who genuinely want to learn, challenge assumptions, and bring new ideas is more important than hiring people who already know the answers.
5. Resilience is the skill that keeps teams moving when conviction turns out to be wrong. Product is a masterclass in rejection. The features you loved most sometimes do not make it. The things you were most certain about sometimes do not grow fast enough. The leader who can get themselves and their team off the mat, take the learnings, and move forward is irreplaceable.
6. The proof of a strong CPO has to be in the pudding. Did the quality and trajectory of the business meaningfully change? Did execution velocity improve? Is the company growing faster and more sustainably? Those questions matter far more than any framework or title.
7. Strong product leadership creates alignment on what not to do, not just what to do. The parking lot of good ideas that the whole organization understands and agrees not to pursue right now is one of the clearest signals that a product leader is operating at a high level.
8. A twice-yearly inclusive planning process with published results builds trust across the entire organization. OpenTable publishes its roadmap to the company, including what they are working on, what they are not, and why, and shows exactly how those decisions ladder up to OKRs. Transparency at that level removes the confusion and politics that slow most organizations down.
9. Execution velocity matters, but impact matters more. Launching 180 features in a year is only meaningful if those features create real change for customers. The combination of speed and impact is the actual measure, not either one alone.
10. AI should be married to the customer problem, not inserted because it is exciting. The question is never whether the technology is cool. It is whether it genuinely helps the restaurant operate better, whether it meets the diner where they are, and whether it creates real value rather than demanding a behavior change that users were never asking for.
11. Reducing handoffs between functions is one of the most powerful ways AI changes product development. The goal is to compress the full cycle from problem understanding to divergent ideation to convergent decision to market, without losing the expertise that each function brings. That compression is where the real productivity gain lives.
12. Restaurant software has muscle memory baked into it, and small changes in high-frequency workflows can cause disproportionate disruption. A feature used 100 times between 7 and 8pm on a Saturday night is a completely different design problem than a feature used once a day. Treating them the same is a fast path to frustrating your most important users.
13. Restaurants are a creative industry, and they want their software to reflect that. No two restaurants aspire to be alike. The 80/20 rule that governs most software products breaks down when your customers define their competitive advantage through differentiation. Meeting them where they are is the unlock for innovation.
14. Relationship building is the first job of any new product leader in hospitality. The first 90 days are not about proving ideas. They are about understanding how specific restaurant groups and diners think about their business, what hospitality means to them, and what version of software meets them where they are.
15. Private dining is a hidden pain point that represents a massive opportunity. People spend an average of 17 hours planning large group events, calling restaurant after restaurant. The restaurant takes on enormous operational and financial risk. Solving that coordination problem with instant booking is exactly the kind of specific, practical problem that creates compounding value.
16. The way product development has worked for the last 20 years is genuinely changing. This is not hyperbole. The processes, the handoffs, the timelines, the roles, and the tools are all in motion at the same time. The leaders who are open to changing how they work, not just what they build, are the ones who will define what comes next.
17. Being agile in a dynamic competitive environment does not mean chasing everything. The restaurant industry is seeing consolidation, new entrants, and verticalization all at once. Staying focused while remaining genuinely responsive to that landscape requires discipline that most organizations have not built.
18. Upskilling teams for AI is as important as building AI features. The internal question of how to help your own people take advantage of what AI makes possible is just as strategic as the external question of what to build for customers. Ignoring one while focusing on the other creates an organization that falls behind on both.
19. Agility applies to process, not just product. OpenTable applies the same experimental mindset to how they work as they do to what they build. If a new process does not work, they change it quickly and intentionally. That willingness to iterate on the operating model itself is what makes speed sustainable.
20. The trajectory question is the most honest measure of product leadership. Not whether the product shipped, not whether the team liked the leader, but whether the business was meaningfully different before and after. That is the standard the best CPOs hold themselves to, and the one worth holding everyone else to as well.