Fractional CTO

When AI writes the code, judgement and accountability really matters.

I'm Lindsay. I make the build/buy/stay call, design the migration, manage the cutover, and run the platform your numbers are tied to. No team to hire. CTO at Context Is Everything; creator of BernardMoves, PlanB Backups and 60 Bubble plugins.

Lindsay Smith

The wedge

Two judgements AI can't make for you

WHAT to build, including whether to build at all

Every translation, briefing, summary, spec - loses nuance. I already speak the four industries I work in, so the brief that goes to the agent is direction, not translation. Sometimes the right answer is to buy off-the-shelf instead of building. I'll tell you that on day one.

HOW to build, including how to land it

Architecture, agent direction, cutover plans, service-level commitments (SLOs), ongoing operation. Vibe coding produces working software. It doesn't land a cutover at 2am or hold a platform to the business KPIs it drives. Engineering is judgement and accountability. I sign up for both.

Slash the backlog

Your backlog, cleared in a month. Then kept clear.

Week one: plug the agent in

I connect a coding agent to your repo, your error logs and your ticket queue. It reads the lot before it touches anything. You get a ranked list of what is actually broken, not what was shouted about loudest.

Weeks two to four: clear it in tiers

Small, safe fixes ship every day, each one tested and reviewed before it merges. Anything that touches money, customer data or a live AI prompt is written up as a decision for you. It never gets slipped in.

Then: keep it clear

You keep the job. It runs on a schedule, fixes what it is allowed to fix, and sends one report each morning, with a burn-down so you can watch the line go down. Ours runs twice a day on BernardMoves.

Tech debt

Tech debt, paid down while you sleep

The secrets nobody can list

Our Stripe key turned out to live in six places. One prompt and four hours later, we had the inventory. How we did it →

The cloud bill nobody reads

$284 a month down to $88. The saving wasn't the interesting part. What we found along the way was. Read it →

The rebuild everyone is scared of

An AI hiring platform, off Bubble and onto Next.js and AWS, in eight working days. The series →

And the quiet stuff: dependency upgrades, dead code, missing tests on old code, copy that drifted away from the product. The robots do it. You stop noticing it was ever there.

Ops without an ops team

I don't have an ops team. I have an agent at the terminal, and rules it can't talk its way around.

Deploys you can trust

Nothing merges on a red build. Nothing deploys that isn't on main. After every release we check the live system, not the green tick.

Every incident becomes a test

When something breaks, the fix ships with a check that runs on every change after it. The same bug doesn't get a second go.

Bugs found before the screenshot

Every browser error is caught and logged, so we hear about a bug before a customer sends us a picture of it. The setup →

Costs you can see

Every resource is tagged by product, so the bill splits cleanly and a surprise shows up early, not at month end.

Don't sweat the small stuff. The robots have it.

Attention is the scarce thing, not code. I spend mine on the calls that matter: pricing, customer data, design, what to build next. The checks, the reviews and the small fixes run without me. How we keep four apps up with two people →

Workshop

Leave with an agent clearing your backlog.

Hands on, on your own repo. We set up the agent, the guardrails and the morning report together, so it is already running when you leave. Small group, limited places.

Register for the October workshop →

Adopting AI · the strategic question

Knowing how to put AI into your business is the question of the next 24 months.

Every business gets that AI will reshape their cost base. Most are stuck in pilot mode, a Claude prompt here, a ChatGPT workflow there, no system. The companies that get this right won't be the ones with the best models. They'll be the ones who put their own context, methodology, customer knowledge, institutional memory, inside the AI.

That's what I co-founded Context Is Everything for. We systematise the move from "AI is a tool we use" to "AI is in the product we sell." Inside delivery, inside the commercial offer, inside the platform itself.

See how it works at Context Is Everything →

What I bring

A senior brain, a team behind it, and a platform when you need one

20+ years across FinTech and enterprise systems

Your industry isn't a learning project. I've been in the room since long before "Fractional CTO" was a phrase.

Adopting AI is the strategic question. I co-founded a company for it.

Context Is Everything systematises how serious businesses move from "we've tried ChatGPT" to "AI is in our delivery, our product, and our commercial pitch." The Contour methodology, the SASHA platform, and a team that's done it before, available when the engagement calls for it.

SASHA platform available

A private on-premise LLM trained on your proprietary methodology, when "AI inside the product" needs to be defensible against generic competitors.

What you're actually buying

The migration is the means. The destination is a business that can stand on its own.

Stability

Predictable infrastructure. SLOs owned and reported, mapped to the business KPIs that matter in your industry. No 2am outages. No compliance time bomb sitting under the business.

Growth-ready

A platform that takes 10× customers, a new product line, a new geography, or an acquirer's due diligence, without rewriting again.

AI inside the team

Build 5× faster with directed AI agents. Lower headcount, better margin, faster cycle time. The efficiency story.

AI inside the product

New capabilities your customers will pay for. A repositioned commercial pitch, AI-native broker platform vs we have software. Higher acquisition multiple. The revenue story.

Numbers you can put on a contract

Platform SLOs mapped to the business KPIs they drive, time-to-bind, FP17 completion, AIP cycle time, audit-cycle time. If platform misses, fixing it is in scope. If business misses with platform green, that's a different conversation. Either way, you stop debating which.

What clients say

Read more testimonials
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