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Road to CTO

Author: 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 [email protected].

8 Episodes
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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 CTOChapters:00:00 La Trace: from a Brittany travel agency to the Tour de France04:35 Leaving to build something in Poland06:38 Two superpowers: the developer's and the CTO's09:13 A three-year-old pronouncing "control" and a first PC built from spare parts14:04 50 applications at 18, one reply: first day of work on his 19th birthday17:00 The interview he thought he failed19:00 Software as craftsmanship: the lesson that stayed21:50 Allianz, Barcelona, and learning to explore what's next door28:33 COVID, a camper van and a village in Kashubia32:49 117 kilometres on a borrowed bike36:09 Quitting the Google process for a message about a bike41:08 1200 kilometres along the Vistula in six days43:38 Advice for juniors in the age of LLMs47:04 Books: Bernard Newman, Sapiens and Nexus49:53 A new postgraduate course in spatial software engineeringFollow MaciejLinkedIn: https://www.linkedin.com/in/maciejgoscinski/La Trace: https://www.latrace.comSpatial 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/059373422XRoad to CTOHosted by Kuba Lang. New episode every Wednesday.Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/All platforms: https://roadtocto.comWant 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 codeChapters:00:00 Happy Hacking: fractional CTO, coach, author01:23 From a 1989 consultancy to a PhD on Erlang and Scala 1.002:51 Employee number seven at the company that became Klarna04:51 From eight developers to 80: what had to change06:55 Tech leads and managers: keeping great developers out of management10:45 "You build it, you own it, you run it"12:33 Three pieces of advice, including shielding the team from the business13:44 The recruiting secret: a niche language as a filter15:20 A sister's calculator and a Commodore VIC-2016:12 A three-part superpower, including the "monkey programmer"17:50 Books: Deep Work, The Creative Act, and two of his own19:39 Stepping down as CTO and leaving after the 2013 Christmas peakFollow ErikLinkedIn: https://www.linkedin.com/in/happi/Happy Hacking and blog: https://happihacking.com/The BEAM Book: https://github.com/happi/theBeamBookThe 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 CTOHosted by Kuba Lang. New episode every Wednesday.Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/All platforms: https://roadtocto.comWant 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 2008Chapters:00:00 Mausool, Dartek and three failed fintechs02:08 The jumper: from mining to banking to Formula One05:06 Leaving the comfort zone after nine years06:20 If you don't know what your people are doing08:39 Follow the trend: what's dying and what's not11:52 Fintech, AI and a prediction for 204016:00 Two weapons: your people and your suppliers18:49 The book: Fintech WarsFollow AmmarLinkedIn: https://www.linkedin.com/in/ammarshaker/Mausool: https://mausool.com/The book "Fintech Wars": https://www.amazon.pl/Fintech-Wars-Titans-Complex-Bestseller/dp/1398617024Road to CTOHosted by Kuba Lang. New episode every Wednesday.Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/All platforms: https://roadtocto.comWant 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 productChapters:00:00 Many hats: enterprise discipline, startup speed01:04 Bipit and the mission of financial education03:47 Two CVs in Dublin, 2001: hired on a staircase07:36 The road: project manager, software house, first startup CTO10:37 Loot: a 20-year-old CEO and 80 people13:30 Why seniors stop getting honest feedback16:12 Did he ever want to be CTO?17:54 AI tools vs the human advisor19:25 Three pieces of advice: a mentor, curiosity, a decision log23:00 The direct debit question that unlocked innovation25:26 Filip's superpowerFollow FilipLinkedIn: https://www.linkedin.com/in/filipjakubowski/Bipit: https://www.bippit.com/Road to CTOHosted by Kuba Lang. New episode every Wednesday.Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/All platforms: https://roadtocto.comWant 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 CTOChapters:00:00 Sporting Rock and the invisible side of sports01:53 A late start: maths first, computers second05:46 From the Max Planck lab to an accidental team lead10:25 What data science really looks like in sports15:42 One metric football gets wrong20:39 Nobody plans to be CTO: advice for engineers23:18 The ego trap23:23 Stefan's superpower: debugging24:54 The book: Turn the Ship AroundFollow StefanLinkedIn: 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/1591846404Road to CTOHosted by Kuba Lang. New episode every Wednesday.Kuba on LinkedIn: https://www.linkedin.com/in/kubalang/All platforms: https://roadtocto.comWant to share your road? [email protected]
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