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Founding AI Technical Lead

💼 Full-time🗓 2026-06-24

Core

Building an AI-powered diagnostic and implementation layer for small businesses (real estate, hospitality, DTC) that connects to their existing systems to deliver specific, actionable insights via email, SMS, or voice.

Role type

Founding AI Technical Lead (Co-founder)

Builds

AI agent workflows, modular building blocks, and a consulting-to-platform business infrastructure

Domain

Small business operations, Real Estate, Hospitality, DTC

Deliverable

production ML models | product features

Required skills

Full-stack architecture, AI agent orchestration, system integrations (POS, accounting, inventory), zero-to-one product building, client-facing technical communication

Preferred skills

Experience as a founding engineer or technical co-founder

Technologies

Claude API, custom tooling, POS systems (Toast, Square), Accounting software (QuickBooks), Property management (AppFolio), Wellness (Mindbody), CRM (Salesforce)

Responsibilities

Own all technical decisions (architecture, stack, tooling), integrate with client systems, build AI workflows for actionable outputs, design scalable modular architecture, communicate technical concepts to non-technical business owners

Seniority

Founding, hands-on IC

Rewrite
## About the Role You're the first technical hire and the third member of a founding team with decades of experience starting, scaling, and operating real businesses across real estate, hospitality, and DTC. You own every technical decision — architecture, stack, tooling, integrations, and eventually hiring your own team. This is a co-builder role with founding-level equity. Here's what your first month actually looks like: you sit in a room with a restaurant owner who knows their numbers are off but doesn't know where. You connect to their POS, their accounting software, their inventory system. You build the thing that tells them exactly what's wrong and exactly what to do about it — and it shows up in their inbox Monday morning in plain English. No dashboards they'll never check. No logins they'll forget. A clear, specific action they can take before the lunch rush. If that excites you more than optimizing a deployment pipeline, keep reading. ## What You'll Build The AI-powered diagnostic and implementation layer for real businesses: - Connect to the systems small businesses actually use — Toast, Square, QuickBooks, AppFolio, Mindbody, Salesforce — and extract insights the owner has never seen - Build AI agent workflows using Claude API and custom tooling that deliver specific, actionable outputs directly to operators (email, SMS, voice — not dashboards) - Design modular "building blocks" so what you build for client #1 accelerates client #2 and client #3 - Create the technical foundation for a consulting-to-platform business that scales beyond any individual engagement - Sit in rooms with business owners, explain what we're building in language they understand, and iterate based on what they actually use ## Who You Are You've shipped real products to real users — not internal tools for engineers, but things that non-technical people interact with every day. You've built from zero at least once in your career, whether as a founding engineer, a technical co-founder, or the first engineer at a startup.
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