First-Time CTO
You just became CTO.
There's no playbook.
No onboarding.
No one to ask.
A survival guide for the loneliest job in startups
Launch price £99 · Save 30%
"The hardest part isn't the technical fires - it's the isolation." - From the conversation that started this book
THE FIRST
CTO
The Job Nobody Explains
You're making decisions alone that could sink the company.
You're hiring engineers for the first time and terrified of getting it wrong.
Your founder changes priorities every week and you're the one who has to make sense of it.
You're context-switching between architecture spikes and homepage copy.
You're wondering if what you're feeling is normal or a red flag.
And there's no one else who holds the full context - no one who understands the weight of it.
You're isolated. You're improvising. And nobody told you this is what the job would actually be.
"The job isn't one job. It's five jobs in a trench coat."
This playbook is everything I learned the hard way - so you don't have to.
What's Inside
Five parts, zero theory
The tactical handbook for first-time CTOs who are making it up as they go
War stories from building fintech platforms where real money moved to real governments - and what I learned the hard way about security, hiring, founders, and staying sane.
Part 1: The Job Nobody Explains
Part 2: Shipping Under Chaos
Part 3: Hiring Before You're Ready
Part 4: Managing the Founder
Part 5: Surviving Yourself
Chapter content subject to change in final version
This book is for you if...
- You just got the title and there's no GitHub repo yet
- You're the only one who holds the full technical context
- You spent today setting up someone's Gmail instead of coding
- You're wondering if you're supposed to still be writing code
- A teammate went directly to the founder because you hadn't given them direction
- You're making architecture decisions that could crater the company and there's no one to ask
This book is NOT for you if...
- You're scaling from 50 to 200 engineers
- You want frameworks for running a mature engineering org
- You're looking for theory - this is war stories and hard lessons
From Chapter 2
The 40% Rule: Where the time actually goes
You think you'll spend most of your time writing code. Here's what actually happens.
- 40% Actual code
- 20% Translating between founder-speak and engineer-speak
- 15% Operations and admin (vendor calls, Gmail accounts, tooling)
- 15% People (hiring, feedback, unblocking)
- 10% Stuff you can't even label
Sample Excerpt
From Chapter 2: "The 40% Rule"
I once spent the entire day "organising Linear" - and honestly I hated it. I hated it because it felt unfamiliar, and I felt zero immediate gratification. You write code, compile it or reload a browser, and you can see the immediate effects; there's a very tight feedback loop.
I had a couple of engineers to manage by that point, and in all honesty, I was doing a terrible job of it. When you're used to building and writing code, you collaborate with people for sure, but you're rarely responsible for guiding how their day looks like.
I remember once, one of my team reached out to the founder directly, asking what exactly it was they were supposed to be working on next. The founder helped him out, and then reached out to me to relay the situation.
My brain filled with justifications and excuses. I had built a reputation based on building great software, but here I was, actively contributing to great software not being built.
This was the first time I truly felt that simply writing code and building features was not going to cut it any more. I needed to fight my gut instincts to spend time just outputting code. I needed to lead. To foster. To be responsible for creating an engineering team I would want to be part of.
Hence: Linear day.
Linear day was boring and unfulfilling but it was necessary and the correct thing to do.
From the Book
Six levels of "ready"
A framework for deciding when to ship
-
1
Does it work for me?
Local dev, happy path only. You're the only one who's seen it.
-
2
Does it work for a technical colleague?
Another engineer can run it. Edge cases start surfacing.
-
3
Does it work for the non-technical stakeholder?
The founder or PM can demo it. UI matters now.
-
4
Does it work for our 100 most fanatical users?
Real usage, real feedback. They'll forgive rough edges.
-
5
Does it work for a cold new signup?
No context, no patience. Onboarding has to hold up.
-
6
Does it work for an influx from a paid campaign?
Scale pressure. Errors cost money. No second chances.
Why This Book Needs to Exist
From CTOs who've lived it
"The hardest part isn't the technical fires - it's the isolation. You're making decisions that could crater the company and there's literally no one else who understands the context."
"Less 'how to scale a 200 person org,' more 'how to survive being the only adult in the room when everything is on fire.'"
"First-time CTO hiring is brutal because you're making irreversible people decisions with almost no signal and no margin for error."
"It blows my mind how tech companies promote without training."
About Me
I've made every mistake in this book
I'm Ben Howdle. I've been CTO at two early-stage startups:
- Letter (3.5 years) - Built the platform from zero, led the engineering team, worked directly with the CEO
- WorkMade (1.5 years) - Promoted from engineer to CTO, managed 6 engineers, shipped financial infrastructure handling real money and tax data
I've also spent 15 years shipping products for companies like Clerk, GoDaddy, Cisco, and Soho House.
I've been where you are. I've made the hiring mistakes, the architecture calls with incomplete information, the founder management failures. This playbook is what I wish I'd had when I started.
Published in Smashing Magazine · Featured in Fast Company & Wall Street Journal · Work adopted by UK Government (Ministry of Justice) · Technical reviewer for O'Reilly and Apress · Speaker at Re:develop, fintech_devcon, and the European Bioinformatics Institute
What People Say
From people I've worked with
"Ben intuitively knows where to cut corners for speed and where shortcuts would come back to haunt us."
"Ben had the rare ability to turn an idea from concept yesterday to a working build in production today. He knew exactly where to focus our energy for the biggest impact."
"His early contributions have saved a potentially limitless amount of developer time, pain and costs down the line."
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Need More Support?
Work with me directly
The playbook gives you the playbook. But if you need someone in your corner for the day-to-day - architecture reviews, hiring decisions, managing up to founders - I offer monthly CTO coaching retainers.
CTO Coaching & Advisory
Weekly calls, unlimited async access, architecture & hiring reviews
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Have questions? Email me at hello@benhowdle.im