Taking more roadmap risk in the AI era

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