Dave Killeen: What to Do When Execs Demand AI
Dave Killeen will tell you, on record, that his relationship with AI has crossed into unhealthy territory. He also says he has never felt more alive, that he is 50 and feels 30, and that he sometimes waits for his two small children to go to bed so he can start a coding session.
In between, he gives Axel Sooriah the most practical answer on this show yet to the question every product team is facing: your exec says "we need AI," and you have no idea what they actually want.
Dave is Field Chief Product Officer at Pendo, with 25 years in product across Mail Online, BBC iPlayer, Badoo, Bumble, and Productboard. He was made redundant, spent seven months unemployed going down AI rabbit holes, got dropped by a search firm for terrifying founders in interviews, and was eventually hired off the back of a YouTube rant about speech-to-text. He now builds Dex, an open-source personal AI operating system, on the side.
What you'll learn:
Why the answer to top-down AI pressure is a KPI driver tree and a career ladder, not an AI strategy
His argument for why the CPO seat turns over faster than any other in the C-suite, and what causes it
Whether delegating thinking to AI erodes your judgment, and his case that it does the opposite
The simplest possible starting point: one chat you never close, voice notes, and a Friday whinge
How to go from that to running your own agent in about ten minutes
What happens when your AI reads your color profile and starts telling you off on a Monday morning
Why he open-sourced Dex, and the frontier-model pricing change that nearly killed it
Why he is now shrinking a model onto the desktop and leaning into locally hosted open source
The two mistakes he'd undo from 25 years: not aligning his exec, and over-protecting his team
Chapters:
00:00: Intro
00:57: Welcome to Product in Practice
02:09: What a Field Chief Product Officer actually does
03:22: From Mail Online to Bumble, then made redundant
05:42: The pressure product teams are under right now
07:41: Why your exec doesn't need AI, they need a driver tree
10:45: Does delegating thinking to AI erode judgment?
11:41: Is AI creative? Meet Dexter
14:38: Making intentional time to go down the rabbit hole
16:45: Start here: one chat, voice notes, and a Friday whinge
19:33: Why this whole thing feels emotional
20:53: Where the curiosity came from
22:43: Explain it to me like I'm five, and the rabbit hole problem
25:56: Crossing into unhealthy territory
28:01: What he would do differently
30:25: What Dex is, and why he open-sourced it
33:45: PMs have always been closeted builders
37:24: The pricing change that nearly killed Dex
38:53: Going local: open-source models on the desktop
40:22: One piece of advice: find the time
41:43: Building without analytics, and what changed
43:26: Where Pendo and Atlassian fit together
45:42: His biggest mistake in 25 years
48:34: Treasure chest: one book, one dish
52:08: Where to find Dave
Connect with Dave: LinkedIn: https://www.linkedin.com/in/davekilleen/
Connect with Axel: LinkedIn: https://www.linkedin.com/in/axelsooriah/
About Product in Practice:
Product in Practice is Atlassian's product podcast, where we dig into how AI is changing the craft of product management. Product leaders show you how they actually work: the tools, the frameworks, and the decisions behind the job. Hosted by Axel Sooriah.
Subscribe so you don't miss the next one.
#productmanagement #PM #atlassian