Road to CTO

There is no job description for a CTO. Ted Ohlsson knows, because his role did not exist until he asked for it. He grew up dyslexic with nobody around who knew IT, planned to drop information systems after his first year at university, spent six years in sales and team management, and then told his manager he wanted something else. The CTO role was created for him.

Ted Ohlsson: CTO for Capgemini's Nordics Dynamics 365 business. He started as a Dynamics 365 CRM application consultant, taught himself to develop because there were no developers around, led teams and sold for six years, and now sets the technical direction of the practice, speaks at conferences and recruits the people he calls the product.

In this episode:

■ Why a kid who planned to leave IT after one year of university ended up running a technology practice

■ The six-year detour into sales and management, and the morning he realised he was losing the technology

■ What a CTO does when there is no product to build: direction, offerings, evangelism, recruiting

■ What he tells aspiring CTOs: focus on what you enjoy, the title takes care of itself

Chapters:

00:00 Capgemini's Nordics Dynamics 365 CTO: "are you asking the right person?"

01:04 Windows 98 and the dial-up noise

02:30 Dyslexic, untechnical, one year from dropping IT

04:05 No developers around: "how hard can this be?"

05:08 Six years of sales and team management, losing touch with tech

07:26 Loving juniors, hating the HR part

07:49 The morning he asked for something else, and the role created for him

08:28 The most undefined role: direction, offerings, evangelism, recruiting

10:41 First time leading: teaching assistant after year one

12:40 Failure as the biggest teacher: inspire, be there, respect

14:05 Advice: never aim to be a CTO, you become one

15:23 Public speaking never ends: live AI demos, humour, your own energy

18:14 Superpower: complex things made simple, drawn not written

19:40 No books: install it and try it

Follow Ted

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

Capgemini: https://www.capgemini.com

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]

David Söderberg hated programming in high school. While loops, for loops, no purpose. What got him hooked was a Flappy Bird clone with his friend's head on the bird, and a feeling he already knew from making techno at 13: write something, see it or hear it instantly. He never chased a CTO role. The role found him because of a job he had left.

David Söderberg: co-founder and CTO of Nettla, a booking and management platform for racket sports clubs, live for a year, now with an AI agent that knows every club's players and price list. Software engineer at Forza Football during his studies at Chalmers, full-stack developer since, padel player by passion.

In this episode:

■ Why music production at 13 was his first programming, and he didn't know it

■ The high school course that made him hate code, and the silly game that reversed it

■ Why he picks jobs by whether he'd be a user of the product himself

■ His main advice: don't chase the title, expand the scope of your problem

Chapters:

00:00 Nettla: the all-in-one platform for racket sports clubs

01:46 Making techno at 13: programming without knowing it

04:41 Hating C++ in high school, loving a Flappy Bird clone

07:12 Chalmers and Forza Football: working on an app he already used

10:15 Build it for yourself: you'll have one user at least

11:44 Side projects: only when you feel like it

13:34 Picking jobs by passion, and the competitor that led to Nettla

15:23 The CTO role he never sought

17:53 Advice: don't chase the title, chase the bigger problem

20:56 Superpower: thinking like the user, building like an engineer

23:32 Why he doesn't read books, and what he does instead

Follow David

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

Nettla: https://nettla.co

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]

Maciej Gościński was halfway through Google's interview process when a friend messaged him about a bike. He quit the process, co-founded a cycling travel company in France, and three and a half years later their maps were on the Tour de France website. His first day of work ever was his 19th birthday, repairing Dell laptops in France. Nothing in between was planned.

Maciej Gościński: ex-CTO and co-founder of La Trace, the French bicycle travel and cartography company that went from a small agency in Brittany to securing Paris-Roubaix and providing maps for the Tour de France. Now building a geographic software product for local institutions in Pomerania and directing a new postgraduate course in Spatial Software Engineering and GIS at the Polish-Japanese Academy of Information Technology.

In this episode:

■ The 50 applications sent at 18 with no experience, and the one company that replied

■ The interview he was sure he had failed, and why taking notes got him hired anyway

■ "Slow is smooth, smooth is fast": the rule that kept his team on schedule for years

■ The superpower that made him a great developer, and why it was useless as a CTO

Chapters:

00:00 La Trace: from a Brittany travel agency to the Tour de France

04:35 Leaving to build something in Poland

06:38 Two superpowers: the developer's and the CTO's

09:13 A three-year-old pronouncing "control" and a first PC built from spare parts

14:04 50 applications at 18, one reply: first day of work on his 19th birthday

17:00 The interview he thought he failed

19:00 Software as craftsmanship: the lesson that stayed

21:50 Allianz, Barcelona, and learning to explore what's next door

28:33 COVID, a camper van and a village in Kashubia

32:49 117 kilometres on a borrowed bike

36:09 Quitting the Google process for a message about a bike

41:08 1200 kilometres along the Vistula in six days

43:38 Advice for juniors in the age of LLMs

47:04 Books: Bernard Newman, Sapiens and Nexus

49:53 A new postgraduate course in spatial software engineering

Follow Maciej

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

La Trace: https://www.latrace.com

Spatial Software Engineering and GIS, postgraduate course at PJAIT: https://podyplomowe.pja.edu.pl/studia/podyplomowe/przestrzenna-inzynieria-oprogramowania-i-systemy-informacji-geograficznej-gis/

Books:

• Baltic Roundabout, out of print and not on Amazon): https://www.goodreads.com/book/show/214512290
• Yuval Noah Harari, Sapiens: https://www.amazon.com/dp/0062316095
• Yuval Noah Harari, Nexus: https://www.amazon.com/dp/059373422X

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]

Erik Stenman was employee number seven at a Swedish startup called Kreditor. He joined as head of engineering, a department of one. Ten years later the company was called Klarna, had 1,200 people, and he had grown with it into the CTO role. His first programming language was Basic on a Commodore VIC-20; his PhD was on compiling Erlang; and the language turned out to be his best recruiting tool.

Erik Stenman: founder of Happy Hacking, fractional CTO, architecture coach and author of The BEAM Book. Former CTO of Klarna, first engineer and employee number seven; before that, project manager of the Scala programming language at EPFL and a PhD in computer science from Uppsala.

In this episode:

■ Why he took the CTO path at all: the job where he didn't get the influence he wanted

■ How a team of eight became 80, and the one structure that kept the good developers coding

■ The hiring trick that gave him three applicants instead of 200, and why it worked

■ Why he stepped down as CTO in 2010 and went back to the code

Chapters:

00:00 Happy Hacking: fractional CTO, coach, author

01:23 From a 1989 consultancy to a PhD on Erlang and Scala 1.0

02:51 Employee number seven at the company that became Klarna

04:51 From eight developers to 80: what had to change

06:55 Tech leads and managers: keeping great developers out of management

10:45 "You build it, you own it, you run it"

12:33 Three pieces of advice, including shielding the team from the business

13:44 The recruiting secret: a niche language as a filter

15:20 A sister's calculator and a Commodore VIC-20

16:12 A three-part superpower, including the "monkey programmer"

17:50 Books: Deep Work, The Creative Act, and two of his own

19:39 Stepping down as CTO and leaving after the 2013 Christmas peak

Follow Erik

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

Happy Hacking and blog: https://happihacking.com/

The BEAM Book: https://github.com/happi/theBeamBook

The Chain (novel): https://readthechain.com/

Other books mentioned: Deep Work (Cal Newport), The Creative Act (Rick Rubin), The Atrocity Archives (Charles Stross), There Is No Antimemetics Division (qntm)

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]

People called Ammar Shaker a job hopper. Fast-moving goods, mining, banking, the founding CIO of the Saudi Formula One Grand Prix, three failed fintechs. He says that is exactly how you learn what a leader actually needs to know, and he has one rule for anyone who wants the title: if you don't know what your people are doing, you don't deserve to lead them.

Ammar Shaker: CTO and co-founder of Mausool, a logistics platform connecting small and medium manufacturers with transport companies, and co-founder of Dartek. Former CTO of multiple fintechs, founding CIO of the Saudi Formula One Grand Prix, 18 years in IT across the Middle East.

In this episode:

■ Why he says being a "jumper" was the best thing that happened to his career

■ The nine-year comfort zone he had to leave, and what he calls the gamble

■ Why he tells every new leader to follow the trend, and which trends he says are dying

■ The two weapons every CTO needs, and the Excel sheet he has kept since 2008

Chapters:

00:00 Mausool, Dartek and three failed fintechs

02:08 The jumper: from mining to banking to Formula One

05:06 Leaving the comfort zone after nine years

06:20 If you don't know what your people are doing

08:39 Follow the trend: what's dying and what's not

11:52 Fintech, AI and a prediction for 2040

16:00 Two weapons: your people and your suppliers

18:49 The book: Fintech Wars

Follow Ammar

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

Mausool: https://mausool.com/

The book "Fintech Wars": https://www.amazon.pl/Fintech-Wars-Titans-Complex-Bestseller/dp/1398617024

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]

In 2001, Filip Jakubowski-Drzewiecki walked into a Dublin design studio with a CV and no job. The manager caught him on the staircase on his way out: can you start tomorrow? Twenty-five years, a failed startup and a digital bank later, he says the most powerful thing he ever learned is to ask the simple question nobody else dares to.

Filip Jakubowski-Drzewiecki: fractional CTO and board member at Bipit, a fintech bringing financial education and certified advisors to people who never had access to them. Previously CTO of Loot, a UK digital bank he helped grow from zero to 80 people, and founder of the boutique consultancy Koia.

In this episode:

■ The failed startup that left him in debt, and the 20-year-old CEO who made him a real CTO

■ Why nobody gives you honest feedback once you're senior, and what he did about it

■ The one habit he recommends to every future leader: a decision log

■ How one simple question in a room full of fintech veterans unlocked a new payments product

Chapters:

00:00 Many hats: enterprise discipline, startup speed

01:04 Bipit and the mission of financial education

03:47 Two CVs in Dublin, 2001: hired on a staircase

07:36 The road: project manager, software house, first startup CTO

10:37 Loot: a 20-year-old CEO and 80 people

13:30 Why seniors stop getting honest feedback

16:12 Did he ever want to be CTO?

17:54 AI tools vs the human advisor

19:25 Three pieces of advice: a mentor, curiosity, a decision log

23:00 The direct debit question that unlocked innovation

25:26 Filip's superpower

Follow Filip

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

Bipit: https://www.bippit.com/

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]

Most people who become CTO never planned it. Stefan Kühn certainly didn't. A mathematician with a PhD from the Max Planck Institute, he took his first industry job and found himself recruiting and running a team within weeks. His advice for anyone chasing the title: don't.

Stefan Kühn: CTO at Sporting Rock, building the software behind sports federations, from licence management to the data that helps football clubs make better decisions.

In this episode:

■ How a mathematician who never wrote Fortran got hired to debug 40-year-old climate models

■ Why leadership landed on him "almost immediately", and why he didn't run from it

■ What data actually says about how a football team wins

■ The one motivation that Stefan says guarantees you'll fail as CTO

Chapters:

00:00 Sporting Rock and the invisible side of sports

01:53 A late start: maths first, computers second

05:46 From the Max Planck lab to an accidental team lead

10:25 What data science really looks like in sports

15:42 One metric football gets wrong

20:39 Nobody plans to be CTO: advice for engineers

23:18 The ego trap

23:23 Stefan's superpower: debugging

24:54 The book: Turn the Ship Around

Follow Stefan

LinkedIn: https://www.linkedin.com/in/stefan-k%C3%BChn-020a34119/

Sporting Rock: https://www.sportingrock.com/

The book "Turn the Ship Around!" by L. David Marquet: https://www.amazon.com/Turn-Ship-Around-Turning-Followers/dp/1591846404

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]

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