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