Chief Technology Officer (Equity-Based | InsurTech)

Location: Connecticut / Remote-friendly (U.S.)
Type: Senior technical leadership — equity-based, pre-raise
Reports to: Founder & CEO

The short version
ORIONN is an early-stage InsurTech company building a data and AI platform that gives independent
insurance agencies capabilities the industry's largest players keep out of reach. The product is already built and
working as a demo. I'm the founder, I've spent 10 years in insurance, and I'm raising a seed round now. (The specifics of what makes our approach different are shared with serious candidates under NDA — see below.) I'm looking for a founding CTO — the most senior technical person in the company, second only to me — to take the platform from working demo to production-grade, secure, scalable product, and to build the engineering function as we grow. This role is equity-based with no salary until we close our seed round — which I'm targeting for mid-to-late Q2 2027, though as with any raise that timing can move. Once funded, it converts to a salaried executive role. I'll be direct about the risk and the upside below, because the right person for this deserves honesty, not a pitch.

What ORIONN is
ORIONN is a data and AI platform for the commercial insurance market. It pairs proprietary industry data with a set of AI-driven tools that streamline how insurance work gets done. The specific components — what the data is, what the tools do, and what makes the approach defensible — are shared with serious candidates once a mutual NDA is in place. Built in FastAPI (Python), with a modular architecture, multiple user portals, and AI integration. It runs today and demos today. The next chapter is making it production-ready — and security is the foundation of everything, because we handle sensitive insurance data.

What you'd lead

• • Technical architecture and roadmap — take the existing codebase to production: database,
• infrastructure, deployment, scale.
• • Security and compliance from the ground up — this is non-negotiable and central. Data security architecture, SOC 2 readiness, encryption, access control. For a platform handling carrier and agency data, security isn't a feature; it's the precondition for the business.
• • AI systems — our AI-driven product features, data pipelines, and responsible-AI practices.
• • Carrier and data integrations — connecting to carrier systems, agency management systems, and data sources.
• • Building the team — as we raise and grow, you hire and lead the engineers who come after you.

Who I'm looking for

• • Deep software engineering experience, with real production systems behind you — not just
• prototypes.
• • Strong security instincts. If "we'll handle security later" makes you wince, we'll get along. Founding CTO — ORIONN, Inc. (Equity-Based | InsurTech) ORIONN, Inc. is an equal-opportunity company. We evaluate candidates on merit and fit, and welcome applicants of all backgrounds. 2
• • Comfortable being hands-on now (writing and shipping code yourself) and a leader later (building a team).
• • Python / FastAPI experience is a strong plus; cloud infrastructure (AWS or similar), databases, and CI/CD expected.
• • AI/ML or LLM integration experience is a meaningful plus.
• • Insurance or fintech background is a bonus, not a requirement.
• • Someone who wants ownership of a problem and a platform — not just a job. Compensation — the honest version
• • Equity: 5%, vesting over 4 years with a 1-year cliff. The cliff means equity is earned over time, aligned with building something real together — your first full year is the mutual trial period, and meaningful ownership accrues as the company and your contribution grow.
• • No salary until we close our seed round, which I'm currently targeting for mid-to-late Q2 2027 (a moving target, as raises always are). Once funded, this becomes a salaried C-level position with market-appropriate compensation, and equity continues to vest.
• • I won't pretend this is a safe bet. It's equity in an early-stage startup that may or may not become something large. I believe in it enough to work without pay myself. I'm looking for someone who sees what I see and wants to build it — and who's protected by real vesting, a clear path to salary, and a genuine ownership stake rather than a promise.

How we'd start
I'd want us to work together for a first stretch before either of us is fully committed — which is exactly what the one-year vesting cliff is built for. It gives us both an honest window to confirm this is the right fit before significant equity is earned, with no awkwardness and no loose ends if it isn't.

About me
Founder and CEO, 10 years in insurance (High Net Worth personal lines and commercial middle-market), entrepreneurial background, currently raising a seed round for ORIONN. I've built the product, the business plan, the investor materials, and the legal foundation. What I need now is a technical leader to build the engine with me.

To apply

Send me a note about yourself, what you've built, and why an early, high-ownership, high-risk technical role appeals to you. Link to your GitHub, portfolio, or anything you're proud of. Serious candidates will sign a mutual NDA before I share the platform and technical details.