Road to CTO

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

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

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

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

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