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
"I love Ben's goal of trying to write Kitchen Confidential for the tech world." - Michael Rispoli, Fractional CTO
The Job Nobody Explains
Not sure yet? Read Chapter 2 free — "The 40% Rule"
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 hardest part isn't the technical fires - it's the isolation."
"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.
After reading this, you'll know how to:
- Make architecture decisions with incomplete information and limited runway
- Hire your first engineers without making expensive mistakes
- Manage the founder relationship when priorities change weekly
- Recognise when you're the bottleneck and shift from builder to enabler
- Communicate technical tradeoffs so non-technical people actually get it
- Define success on your own terms, not the market's
Page 38
"The job isn't one job. It's five jobs in a trench coat pretending to be one job." - I feel seen, I feel this in the core of my being.
What's Inside
Five parts, zero theory
Painful lessons 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.
Painful lessons first, advice second. Every chapter starts with a specific moment - something that actually happened - and ends with what I'd tell someone facing the same thing.
Intro: Why I Wrote This
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
Outro: The Job Stays the Same
Plus: Frameworks & FAQs
10 practical answers from real CTO questions, covering everything from making decisions with incomplete information, to where to find engineers who thrive in chaos, to what to do when production is on fire at 2am.
What You Get
The Playbook + Toolkit
Everything you need to start strong
The First CTO (PDF, ePub, Mobi)
15 chapters, intro, outro, plus Frameworks & FAQs
First 90 Days Checklist
Week-by-week checklist for your first three months. What to learn, who to talk to, what to ship, and what to resist changing.
Hiring Rubric
Candidate scoring sheet with seven criteria, a red flags checklist, and interview format guidance. Print one per candidate.
Delegation Handoff Template
Fillable form for handing off projects. Covers scope, goals, the delegation framework, and a CTO self-check.
Weekly CTO Self-Audit
Repeatable Friday check-in. Track your time split, spot bottlenecks, log what shipped, and write one thing to change next week.
Founder Conversation Prep Sheet
6-step worksheet for difficult founder conversations. Translate tech to business impact, pre-empt objections, prepare your script.
Monday Actions Tracker
15-week programme with one action per chapter. The actions that drift become your personalised development plan.
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 painful lessons and hard-won advice
"Develop the skills you were maybe shying away from. Outputting good code is going to be a bit more of a commodity than it was before. The skills that surround your whole value - product sense, talking to customers, communicating trade-offs - those are going to be more important than they used to be."
Sound familiar?
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 actually manage. 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.
Ready to read the rest?
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
"I love Ben's goal of trying to write Kitchen Confidential for the tech world. Being the first CTO is a lot different to being the CTO at a company like IBM. You need to be scrappy, nimble, a leader, but also a coder, and everything in between."
"Your first 3 engineering hires will define your culture more than any manifesto. Hire for clarity of thought over years of experience."
"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."
"The hardest parts are the things nobody writes about because they happen before there is a team, a process, or anything that resembles stability."
"Not every shortcut is bad debt. If it buys you 3 months of runway and can be refactored in 2 weeks, take it. The trick is tracking what you borrowed."
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
Hear the Story Behind the Book
Becoming The First CTO
I sat down with Michael Rispoli to talk about what it's actually like being a first-time CTO at an early-stage startup, how the book came together, and the mistakes that shaped every chapter.
With Michael Rispoli · The no bullsh*t CTO
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."
"The API we built together was still the foundation they built new products on, years after I'd left."
Choose Your Package
Get the playbook
~25,000 words. Read it in a weekend, reference it for years.
Book Only
- The First CTO in PDF, ePub, and Mobi
- 15 chapters, intro, outro, plus Frameworks & FAQs
- DRM-free, read anywhere
Playbook + Toolkit
Everything in Book Only, plus:
- First 90 Days Checklist
- Hiring Rubric
- Delegation Handoff Template
- Weekly CTO Self-Audit
- Founder Conversation Prep Sheet
- Monday Actions Tracker
Both packages include instant delivery via email. DRM-free.
Need More Support?
Work with me directly
The playbook gives you the lessons. But if you need a senior technical voice in your corner for the day-to-day, I offer three ways to work together.
Async only
Advisory Retainer
Unlimited Slack and email access. Gut-checks, quick reviews, sanity checks. Cancel anytime.
Calls + async
CTO in Your Corner
Weekly 30-minute call, unlimited async access, architecture reviews, hiring input, founder communication strategy. Cancel anytime.
One-time engagement
Embedded Sprint
Two weeks embedded with your team. Full audit of tech, team, and roadmap. Option to continue with a monthly retainer.
Not Ready Yet?
Read Chapter 2 free
Not sure yet? Join the mailing list and get Chapter 2 ("The 40% Rule") as a free PDF, plus occasional tactical advice on the CTO job.
Have questions? Email me at hello@benhowdle.im