Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing. In today's episode, we discuss: Why a CPO's number one job is raising their team’s ambition, not shipping features How to demand the best from your team without creating a fear-based culture Why organizational politics is actually an incentives problem How Diya is “militant” with her calendar to carve out dedicated thinking time Why you should avoid chasing titles in your career - and what to chase instead References: Google: https://www.google.com Melio: https://meliopayments.com Okta: https://www.okta.com Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/ Xero: https://www.xero.com Where to find Diya: LinkedIn: https://www.linkedin.com/in/diyajolly Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:12 How an excellent CPO makes an impact on the business 02:01 How the CPO role shifts under founders vs hired CEOs 03:38 Influencing a founder without going deferential 07:37 How adding value to customers is always a net positive 08:45 Why roadmaps need more risk in the AI era 12:30 How to shelter innovation teams from the existing system 15:12 What's different about being a great CPO in 2026 17:34 How AI has changed the concept of an app 18:28 It’s essential for CPOs to fly at a low altitude 20:34 How misaligned incentives cause organizational politics 25:13 Being demanding without creating a fear-based culture 28:10 Why raising ambition is a CPO's number one job 31:39 The boss who taught Diya to keep raising the bar 32:43 The hardest part of being a CPO 35:28 The three buckets Diya uses to delegate 36:30 How Diya protects deep-work time on her calendar 42:45 Xero’s game-changing early bet on AI insights 44:58 How far into the future should CPOs plan for? 47:14 What it takes to be an excellent C-suite member 48:53 Why ambitious PMs should chase impact, not titles 50:28 The four bottlenecks that stall career growth