At six, Paweł Sobkowiak wrote his first program on a Commodore 128. In high school he quit coding to study sociology. He came back to build the engineering team behind Booksy, from a handful of people to 180.

Paweł Sobkowiak: CTO at Mos Health, building an AI companion for employee wellbeing. Previously 11 years at Booksy, where he grew engineering from a side project to 180 engineers and was the de facto CTO years before the title.

In this episode:

■ The Git branch he created as a junior in 2009 that nobody wanted, and what it changed

■ Why he was doing the CTO job years before anyone called him CTO

■ The one habit that got him promoted every time, without asking

■ Why he thinks engineering specialists are becoming a thing of the past

Chapters:

00:00 Mos Health and the AI companion for wellbeing

01:10 A Commodore 128 and a first program at six

02:19 Quitting code for sociology, and the crawler that brought him back

04:44 Why the CTO role is a business role

06:42 Junior at Sensei Soft: Git, tests and thinking like the user

12:38 Booksy: from side project to 180 engineers

14:26 The crisis that made him the official CTO

21:39 The cheat sheet: ownership and listening to people

26:21 Paweł's superpower

28:28 Engineers, not coders: why roles are dissolving

33:21 The book: Extreme Ownership

Follow Paweł

LinkedIn: https://www.linkedin.com/in/pawelsobkowiak/

Mos Health: https://moshealth.com/

The book "Extreme Ownership" by Jocko Willink and Leif Babin: https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs/dp/1250067057

Road to CTO

Hosted by Kuba Lang. New episode every Wednesday.

Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/

All platforms: https://roadtocto.com

Want to share your road? [email protected]

An officer in the Italian Army at 18. CIO and CTO of a city that didn't exist yet at 40. Alessio Garofalo's road to the top had no map, and that's exactly why it's worth hearing.

Alessio Garofalo: former CIO and CTO of NEOM, Amazon leadership across the UK and Japan, now leading transformation at NATO in Portugal.

In this episode:

■ Why he never once hired above his team, and what it cost him

■ The rule he gives every future CTO: get your hands dirty first

■ What people want from a leader, and why it's the same on every continent

■ Why waiting to be offered an opportunity fails 90% of the time

Chapters:

00:00 From the Italian Army to NEOM and NATO

03:30 What people want from a leader, on every continent

04:36 Public sector vs private: the same decisions, different drivers 07:12 Robotics, security and the trends worth watching

10:17 The real job of a CTO is not technical

13:25 Three rules for future CTOs (and a bonus one)

16:01 The book: "City by Mistake"

17:27 Alessio's superpower

Follow Alessio

LinkedIn:

https://www.linkedin.com/in/alessiogarofalo1985/

Alessio's book "CTO by Mistake":

https://www.amazon.com/CTO-Mistake-Survival-Alessio-Garofalo/dp/B0C4MVSHHY

Road to CTO. New episode every Wednesday.

Hosted by Kuba Lang.

Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/

All platforms: https://roadtocto.com

Want to share your road? [email protected]

Welcome to Road to CTO - the podcast designed for software engineers, tech leads, and aspiring engineering leaders making the transition from writing code to steering technical strategy and leading teams.

In this trailer, we dive into what this show is all about:

• Real-world insights on technical leadership and scaling engineering teams.
• Navigating trade-offs between business goals, architecture, and tech debt.
• Lessons learned from experienced CTOs and tech founders.
  

Subscribe now to never miss an episode as we unlock what it really takes to become a successful CTO.

Website: roadtocto.com