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All Episodes

The CTO Compass — 42 episodes

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Title
1

Break “Can't Culture”: How to Get Your Team to Tell You the Truth ft. JL Heather

2

What to Do When Your Team Is Scared AI Will Replace Them ft. Angela Mulrooney

3

Why The Best Engineering Managers In 2026 Code More, Not Less ft. Alex Ponomarev

4

People Over Clients Over Projects (Why Most Agencies Rank It Wrong) ft. Dominic Tancredi

5

The Model Doesn't Matter: What Actually Creates 10x AI Productivity ft. Clive Moore

6

Stop Panic-Buying AI: The Silver Bullet Myth That's Making You Slower ft. Asim Kumar

7

Why Dropping AI Into a Broken Process Makes Everything Worse ft. Mike Toguchi

8

3 Critical Career Mistakes Engineering Leaders Make ft. Limor Bergman Gross

9

Your AI Strategy Will Fail for the Same Reason Your Last ERP Did ft. Abhijit Verekar

10

Why Organizational Change Fails: The Hidden Politics and Self-Interest Killing Your Transformation ft. Bud Caddell

11

We Sacrifice People for Performance. AI Is About to Make That Impossible ft. Margôt van Brakel

12

How User Psychology Grew a Dating App to 17 Million Users With Almost No Marketing Budget ft. Colin Hodge

13

Why 95% of AI Pilots Deliver Zero Business Impact and How to Fix Your Foundation ft. Matt Soltau

14

The Software That Can’t Be Wrong: Building Fintech for Millions in Africa ft. Erioluwa Asiru

15

3 Ways to Build AI Systems That Survive the Real World ft. Sairam Sundaresan

16

AI Risk Is a Design Problem: 3 Questions Every CTO Should Ask Before Their Next AI Release ft. Jill Stover Heinze

17

AGENTS.md Won’t Save You: Design AI Systems You Can Actually Control ft. Craig Kaplan

18

Why Treating AI Like Software will cause Most AI Initiatives to Fail ft. Stephanie Sylvestre

19

Why CTOs Burn Out when the Pressure to Deliver Keeps Rising ft. Andrew Hinkelman

20

Why Enterprise AI Keeps Disappointing (hint: CoPilot isn’t the Problem) ft. Santosh Kaveti

21

The Hidden Complexities of SaaS Pricing, CPQ, and Quote-to-Cash ft. Tina Kung

22

Why Smart Tech Leaders Become the Bottleneck (and How to Get Out of the Weeds) ft. David Hori

23

Hiring Is Broken for Tech Leaders. Here’s What Actually Works Today ft. Bill Kasko

24

How to Spot Revenue Leaks and Align Tech to Business Goals. Lessons from a Fractional CTO ft. Matt Dixon

25

Beyond the Lone Genius: Telle Whitney on Rethinking Leadership for Today’s CTOs and CIOs

26

The 80/20 that Actually Moves the Needle ft. Loic Potjes

27

RaiseAI: Cutting the Time for a Capital Round in HALF ft. William Hollis

28

Reinventing Talent: on Clarity, Culture, and AI w/ Scott Morris

29

Don’t Wait for All the Data: on Courage, Culture, and AI ft. Margaret Heffernan

30

Revolutionizing Logistics with AI ft. David Soileau

31

The Future of Work: AI and Human Roles ft. Mike Todasdo

32

Debunking Innovation Myths ft. Coby Skonord

33

Building a Health Tech Revolution ft. Bart Spangenberg

34

Revolutionizing Audio Production with AI with Peadar Coyle

35

Navigating Government Contracts as an Expat with Tony Kyriakidis

36

Navigating the Future of Remote Work with Nola Simon

37

Visionary and Integrator Dynamics with Kelsey Daingerfield

38

The Future of Software Development with Ahmed Bashir (DevRev)

39

From Spreadsheets to AI Agents with Zulfiya Forsythe

40

From Tinkerer to CTO with Mattia Peiretti

41

The Journey of a Global Leader w/ Niranjan Sridhar

42

Revolutionizing Customer Service with AI w/ Mattieu Detaille