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

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"I love Ben's goal of trying to write Kitchen Confidential for the tech world." - Michael Rispoli, Fractional CTO

By Ben Howdle · two-time startup CTO

THE FIRST CTO

The Job Nobody Explains

Ben Howdle

Reader reviews

Amazon review

★★★★★ Verified

"It's like Ben is inside my brain, validating my thoughts before the situations even arise."

"If you're transitioning into technical leadership, this book is a no-brainer. I've known Ben since the very start of our careers 15 years ago, and his proactive approach to the industry has always been inspiring. Now, as I embark on my first CTO role, his book The First CTO has been a revelation. It's rare to find a resource so succinct that makes you feel so understood; it's like Ben is inside my brain, validating my thoughts before the situations even arise. Ben, I'm adding you to my inner circle. This book is zang."

Phillip Penny
Phillip Penny

Fractional CTO

Amazon review

★★★★★ Verified

"I can't really express how amazing it was reading this to feel seen. Actually seen."

"An absolutely brilliant book that spoke to the soul of the job. I can't really express how amazing it was reading this to feel seen. Actually seen. To show what the job entails and how much you actually take on. How much your role changes from being a software engineer to being a CTO, how you move further and further away from doing the code and doing things yourself, to managing what reaches the CEO, what reaches the executive team."

Michael Lockett
Michael Lockett

Founder/CTO at Symbiometry

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

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

01
"CTO" Is a Fake Title
What the first week felt like - and what nobody warned me about.
02
The 40% Rule
Your technical skills are now less than half the job.
03
Your Real Boss
The founder relationship is the job. Everything else flows from it.

Part 2: Shipping Under Chaos

04
Architecture Decisions at 2am
Making technical bets with incomplete information.
05
When to Cut Corners
Speed vs. quality is a false choice. Knowing where to cut is the skill.
06
The First Deploy
Shipping v1 when nothing is ready.

Part 3: Hiring Before You're Ready

07
Your First Hire Will Probably Be Wrong
Why the first engineering hire is the hardest.
08
The Team You Didn't Build
Inheriting engineers you didn't hire - and making it work anyway.
09
High Output, High Maintenance
Hiring brilliant engineers who are difficult to work with.

Part 4: Managing the Founder

10
The Weekly Pivot
Founders change priorities constantly. That's their job.
11
Saying No
The features that'll kill you and the conversations that save you.
12
Translating for the Room
Communicating technical tradeoffs so non-technical people actually get it.

Part 5: Surviving Yourself

13
The Bottleneck Is You
Recognizing when you're the thing slowing everything down.
14
"I'll Just Fix It Myself"
The trap of doing instead of delegating.
15
What Success Looks Like
It's not what you think.

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?

Buy the Book - £12 See all options

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.

"I was mortified. I felt awful. I felt called out. I felt seen. I felt exposed. I felt under-qualified. Plainly; I felt stupid."

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?

Buy the Book - £12 See all options

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."

Michael Rispoli

Fractional CTO, Host of CTO Confidential

"Your first 3 engineering hires will define your culture more than any manifesto. Hire for clarity of thought over years of experience."

Gagan Deep Singh

CTO

"Less 'how to scale a 200 person org,' more 'how to survive being the only adult in the room when everything is on fire.'"

Gino Ferrand

Founder, GILD

"First-time CTO hiring is brutal because you're making irreversible people decisions with almost no signal and no margin for error."

Harish Ramakrishnan

Founder, JobsifyAI

"It blows my mind how tech companies promote without training."

Tessa Kriesel

Developer Relations

"The hardest parts are the things nobody writes about because they happen before there is a team, a process, or anything that resembles stability."

Dan Bedford

CEO, Connexion

"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."

Gagan Deep Singh

CTO

Get the playbook - from £12

About Me

I've made every mistake in this book

Ben Howdle

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 16+ 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."

Chase Croft

Head of Product

"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."

Nick Simpson

Founder, WorkMade

"The API we built together was still the foundation they built new products on, years after I'd left."

Jamie Edwards

CEO, Kayako

Choose Your Package

Get the playbook

~25,000 words. Read it in a weekend, reference it for years.

Book Only

£12
  • The First CTO in PDF, ePub, and Mobi
  • 15 chapters, intro, outro, plus Frameworks & FAQs
  • DRM-free, read anywhere
Buy the Book - £12
Complete Package

Playbook + Toolkit

£79

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
Buy the Toolkit - £79

Both packages include instant delivery via email. DRM-free.

Purchasing power parity pricing applied automatically based on your location.

Also available on Amazon

Kindle · Paperback

Need a senior CTO in your corner?

The book is the lightest-touch version of how I work with founders. If you need ongoing strategic support, architecture reviews, or hands-on engineering leadership, I offer fractional CTO engagements starting at £6,000.

Learn about working together

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

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The First CTO - from £12

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