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Fractional CTO

Get off Bubble without losing the business that grew on it.

Industry-deep Fractional CTO for insurance, healthcare, regulatory ops, and lending. I make the build/buy/stay call, design the migration, manage the cutover, and run the platform your numbers are tied to. No translation tax. No team to hire.

Book a Compliance & Migration Audit See the three engagements

The wedge

Two judgements AI can't make for you

WHAT to build — including whether to build at all

Vibe coding has become a commodity. Knowing what to type hasn't. Every translation hop — business reality → agency → spec → LLM — loses nuance. You spend the first six weeks teaching a junior what a binder, an endorsement, a treatment plan, or a loan-stage waterfall actually means. By the time their spec reaches the LLM, it's a junior's understanding of your business.

I already speak the four industries I work in. The brief that goes to the agent is direction, not translation. Same agent. Sharper instructions. Better code. And sometimes the right answer is to retire the build entirely and adopt the vertical SaaS that already exists. I'll tell you that on day one.

HOW to build — including how to land it

Architectural decisions, agent direction, sequencing of work, cutover plans, service-level commitments (SLOs), ongoing operation. The operational craft of getting the thing into production and keeping it there against the business KPIs it drives.

Vibe coding produces working software. It doesn't produce the right software for an insurance customer who renews thirty days late, and it doesn't land a cutover at 2am. Engineering is judgement and accountability. I sign up for both.

Industries

The four businesses I don't need translated to me

Domain depth on day one. No six-week onboarding to learn what time-to-bind means, or what a consent record has to prove to an auditor, or why an AIP cycle has three failure modes.

Insurance

I know what a renewal-late-payment edge case does to a broker's cashflow — and which fields the binder system has to capture before cover is bound.

Vocabulary in play: time-to-bind · loss-ratio · premium leakage · MGA binder authority · endorsement cycle · claims-pend-rate

20+ years across FinTech and enterprise systems · ex-CTO at Telrock

Healthcare & dental case management

I know what a consent record has to prove to an auditor, not just what it has to show on screen. I built DentalInker.

Vocabulary in play: consent-completion · recall rate · chair utilisation · hygienist-time-per-patient · treatment-plan acceptance · FP17 (NHS dental claim)

DentalInker case study →

Regulatory & compliance ops

I know what 'evidence' means to a regulator, not just to a developer.

Vocabulary in play: audit-cycle time · evidence-pack turnaround · attestation completeness · control-test-pass-rate · AML alert-clear-rate · breach-notification SLA

Security & application review → · PlanB Backups →

Mortgage & lending

I built a mortgage marketplace in Bubble. I know what a stage-waterfall looks like end-to-end.

Vocabulary in play: time-to-decision · fall-through rate · broker NPS · conversion-by-stage · AIP cycle time · packaging completeness · mandate margin

Mortgage marketplace case study →

If you're not in one of these four, I'll happily tell you who to call. I only take projects in industries I already know.

Accountability

Accountable for the numbers — both kinds

Most consultants ship a platform and hand back a list of latencies. I commit to the SLOs that matter — uptime, response time, throughput on the critical workflows — and I map each one to the business KPI it actually moves.

In insurance, that's quote-to-bind conversion and claims processing throughput. In dental case management, hygienist-time-per-patient and consent-completion rate. In regulated ops, audit-cycle time and evidence-pack turnaround. In lending, time-to-decision and broker NPS. The link from page-load to revenue isn't theoretical — in your industry I already know where the leverage is.

We instrument the link. We report it monthly. We hold the platform to it. If the platform is hitting its numbers and the business isn't, that's a business problem. If the business is hitting its numbers and the platform isn't, that's mine to fix. Either way, you stop debating which.

How we work together

Three engagements, low to high commitment

Start with the audit. Most clients start there. The next two are optional, decided once we both see the lay of the land.

Backing infrastructure

When the engagement needs more than one brain

I'm CTO at Context Is Everything, an AI systems company with the thesis that organisational context — the methodology, customer knowledge, and institutional memory that only your firm has — is what mass-market AI can't replicate. When an engagement calls for it, I bring the CIE team and platform with me.

The team
Robbie MacIntosh (crisis ops and operational transformation) and Spencer Thursfield (commercial and brand) come with me when the engagement needs them. We've been doing this together long enough to move fast.
The methodology
The Contour methodology and Ring Model — CIE's frameworks for separating public context from organisational context — are the structural backbone behind the migration plan when the platform needs to encode proprietary knowledge.
The SASHA platform
A private on-premise LLM trained on your proprietary methodology. Available as the foundation when "AI inside the product" needs to be defensible against generic competitors — claims-triage rules, underwriting patterns, treatment protocols.
Proof

Years in these industries. Not weeks of catch-up calls.

Healthcare & dental

DentalInker case management

A dental case management platform built on Bubble — consent capture, recall workflow, treatment planning.

Mortgage & lending

Mortgage marketplace in Bubble

A two-sided marketplace for mortgage brokers, end-to-end stage-waterfall management.

Regulated workflows

Bullhorn ATS integration

Plugging a regulated recruiting workflow system into Bubble apps — consent capture, audit trail, candidate data lifecycle.

About

I'm Lindsay.

Twenty years in enterprise software, the last decade deep in Bubble — PlanB Backups, sixty Bubble plugins, and the migrations that pay the rent. I'm CTO at Context Is Everything, and these days I take selected Fractional CTO engagements in the four industries above — insurance, healthcare & dental case management, regulatory and compliance ops, and mortgage & lending.

I only take work in those four industries. If your business is close but not exact, I'll be honest about whether I'm the right person. I'd rather lose a sale than overpromise on a domain I don't know.

Book a Compliance & Migration Audit Or just email me

FAQ

Questions worth answering

Why only four industries?

Because depth is what AI changed. Vibe coding produces working software. It does not produce the right software for an insurance customer who renews thirty days late. The translation tax between a generalist's understanding of your business and the agent's prompt is real, and it bleeds the project budget. In four industries I already know cold, that translation tax is zero. In the fifth one, it isn't — so I don't take work there.

Can't I just vibe code the migration myself now?

You can vibe code the software. You can't vibe code understanding the customer. The expensive mistakes in regulated industries aren't bugs — they're shipping the wrong workflow for a customer scenario you didn't know existed, or missing a compliance artefact that surfaces during the next audit. That's the part I'm paid to prevent.

Hire an agency vs you?

An agency adds a translation hop. Your business reality has to be briefed to the agency, then specced by an analyst, then handed to the agent. Each hop loses nuance. I am the hop you're trying to remove — one human, already domain-fluent, directing the agents directly. When I need more bandwidth, I pull from the Context Is Everything team, not from a contractor pool.

What if the right answer is not to migrate?

Then I'll tell you on day one. The audit costs the same. The "buy" path is often right in regulated industries where serious vertical SaaS exists — I'd rather lose a migration project than ship the wrong decision.

What does the relationship look like after the migration?

A retained Fractional CTO seat. We've just rebuilt the platform you'll run for the next five years. Someone has to own the roadmap, the AI direction, the build/buy decisions, and the SLOs. That's the job I want.