Industry-deep across insurance, healthcare, regulatory ops, and lending — and the consultancies that serve them.
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 translation tax. No team to hire. CTO at Context Is Everything; creator of PlanB Backups and 60 Bubble plugins.
Or if your platform is how you deliver, visit Context Is Everything →
The wedge
Vibe coding has become a commodity. Knowing what to type hasn't. Every translation hop — business reality, agency, spec, LLM — 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.
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.
Where I work
What I bring
Your industry isn't a learning project. I've been in the room since long before "Fractional CTO" was a phrase.
Robbie MacIntosh (crisis ops and transformation) and Spencer Thursfield (commercial and brand) come with me when the engagement calls for it. The Contour methodology and Ring Model are 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
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.
A platform that takes 10× customers, a new product line, a new geography, or an acquirer's due diligence — without rewriting again.
Build 5× faster with directed AI agents. Lower headcount, better margin, faster cycle time. The efficiency story.
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.
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.
Same conversations keep coming up. AI that works in a demo but not in production. Apps that outgrew their platform six months ago. Projects that failed before anyone opened an editor. I write about the stuff I actually see.
Five layers that separate a working agentic system from a chatbot with delusions of competence. We learned this the hard way.
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The concentrated version: seven lessons and three surprises from migrating a production Bubble app to a custom stack with AI.
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Nobody mentions the responsibilities until they’re yours. Hosting, security, backups, CI/CD—all of it.
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When building is cheap, the cost of building the wrong thing goes up, not down. The economics have flipped.
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