Road to CTO

Kuba Lang
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Short stories of how technology leaders got to where they are. One CTO, one journey, no filler. New episode every Wednesday. Road to CTO is a short-format podcast for engineers and engineering managers aiming for the CTO role, and for tech leaders curious how their peers got there. Each episode is one conversation about the path, the turning point, and the lessons learned along the way. Guests range from first-time startup CTOs to engineering leaders at global scale-ups. Hosted by Kuba Lang, CEO of Cyrantos, who has spent the last decade helping companies hire technology leaders. Want to share your road? Reach out at hello@roadtocto.com.

Episodes

  1. 1d ago

    #7 - Maciej Gościński: Star developer? La Trace's CTO says that skill dies at the top

    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/214512290Yuval Noah Harari, Sapiens: https://www.amazon.com/dp/0062316095Yuval 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? hello@roadtocto.com

    #7 - Maciej Gościński: Star developer? La Trace's CTO says that skill dies at the top

  2. Oct 21

    #6 - Erik Stenman: Promoting your best coder to manager? Klarna's first CTO says don't

    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? hello@roadtocto.com

    #6 - Erik Stenman: Promoting your best coder to manager? Klarna's first CTO says don't

  3. Oct 14

    #5 - Ammar Shaker: Don't know what your people do? You don't deserve to lead them

    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? hello@roadtocto.com

    #5 - Ammar Shaker: Don't know what your people do? You don't deserve to lead them

  4. Oct 7

    #4 - Filip Jakubowski-Drzewiecki: Afraid to ask the simple question? That's where innovation starts

    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? hello@roadtocto.com

    #4 - Filip Jakubowski-Drzewiecki: Afraid to ask the simple question? That's where innovation starts

  5. Sep 30

    #3 - Stefan Kühn: Want to be CTO for your ego? That's the fastest way to fail

    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? hello@roadtocto.com

    #3 - Stefan Kühn: Want to be CTO for your ego? That's the fastest way to fail

  6. Sep 23

    #2 - Paweł Sobkowiak: From sociology student to Booksy's 180-engineer CTO

    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? hello@roadtocto.com

    #2 - Paweł Sobkowiak: From sociology student to Booksy's 180-engineer CTO

  7. Sep 16

    #1 - Alessio Garofalo: From army officer to CTO of a city of the future

    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? hello@roadtocto.com

    #1 - Alessio Garofalo: From army officer to CTO of a city of the future

  8. Sep 13

    Road to CTO: Trailer

    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

  • 1 Trailer
    7 Episodes

Trailer

About

Short stories of how technology leaders got to where they are. One CTO, one journey, no filler. New episode every Wednesday. Road to CTO is a short-format podcast for engineers and engineering managers aiming for the CTO role, and for tech leaders curious how their peers got there. Each episode is one conversation about the path, the turning point, and the lessons learned along the way. Guests range from first-time startup CTOs to engineering leaders at global scale-ups. Hosted by Kuba Lang, CEO of Cyrantos, who has spent the last decade helping companies hire technology leaders. Want to share your road? Reach out at hello@roadtocto.com.

Information

  • Creator
    Kuba Lang
  • Years Active
    2026
  • Episodes
    8
  • Rating
    Clean
  • Copyright
    © 2026 Kuba Lang
  • Show Website
    Road to CTO