We pair 30+ years in the founder's chair and the C-suite, as COO, CFO, CRO, and CTO, with today's AI to turn what is in your head into something real. Get hands-on with a live mockup session, chart the path with an AI Strategy Sprint, or bring us in as your fractional Chief AI Officer.
Talk to usWhere to start
Most leaders are already using AI to turn ideas into something they can see and touch. The quickest way in is a live mockup session. Get on a call with us and watch what is in your head become a working prototype, right there on the screen. It is a low-pressure way to get your feet wet, and you walk away with something real to build on.
Get your feet wet. In one working session we turn what is in your head into a clickable prototype, live, and hand you something your developers can build from.
Explore Live Mockup →Turn AI uncertainty into a costed, prioritized roadmap your team can actually act on.
Explore the Sprint →Embedded AI leadership that takes the roadmap and executes it, without a full-time hire.
Explore Fractional CAIO →What We Build
Design and deploy intelligent workflows that eliminate manual processes across sales, marketing, support, and operations.
Unified dashboards consolidating Stripe, Salesforce, and accounting data with MRR tracking, cohort analysis, and AI-powered querying.
Automated lead enrichment, scoring, deduplication, and real-time research that turns raw data into qualified conversations.
Sentiment analysis, intelligent ticket routing, and personalized auto-responses that prioritize urgent issues automatically.
AI-generated content pipelines with multi-layer QA agents that catch hallucinations and enforce accuracy.
Connect disparate systems — CRMs, payment processors, APIs — into unified, queryable platforms.
Purpose-built tools: tax filing systems, release notes platforms, subscription trackers, onboarding flows.
Founder-level operational strategy: KPIs, process design, financial controls, team scaling, M&A readiness.
Solutions We've Built
Lead intelligence that catches buying signals before your competitors do. Revenue platforms that finally consolidate the chaos of Stripe, Salesforce, and accounting into one honest picture. Support systems that know which customers are about to blow a gasket — and respond before they do. Content pipelines with AI agents checking AI agents, because getting the technology right is only half the battle. These systems work not because they were built by a developer, but because they were designed, pressure-tested, and refined by someone who has sat in the C-suite, managed the P&L, and knows what actually moves a business forward.
Get to know me
Hi, I'm Chris Labatt-Simon, principal of Fair Winds Strategies, and a founder-turned-operator with a love for building AI-powered platforms that actually work. I've spent 30+ years leading technology companies — as a CEO who built a $12M business from scratch (Inc 500, multiple years), as CIO driving operational transformation across 150-person organizations, and as COO & CFO scaling a SaaS company to 50%+ growth. I've sat in the trenches, the C-suite, and on boards of both startups and non-profits — so I see things from every angle. But I've never coasted on experience. I stay deep in the latest approaches to sales, marketing, support, finance, app development, and AI — combining modern, forward-thinking strategy with the pattern recognition that only comes from decades of doing it for real.
Learn More →“Chris's experience acts as a cheat code for startups on the path to success… As my second and a crucial member of my C-suite, Chris has given us a serious competitive advantage that helped make us a recognized name in our space.”
Jason Nadaf, Founder & CEO, SureDone
“Chris played an integral role in the acquisition of several businesses… He transformed our web design department from an expense to a revenue generator and introduced numerous strategies to optimize efficiency.”
Jim Boykin, Founder & CEO, Internet Marketing Ninjas
Insights & Articles
My wife used to buy books from Barnes & Noble online. This was the late nineties. The deal was something like spend twenty dollars, get twenty dollars off, new...
A practical 90-day framework showing exactly how a fractional Chief AI Officer audits shadow AI, deploys multi-agent systems, and delivers measurable ROI for mid-market companies.
The complete technical stack a fractional Chief AI Officer deploys in mid-market companies. From model selection to agent orchestration to production monitoring.
