Founding AI Engineer

About us We leading telehealth brands recover lost customers with our realtime 1:1 SMS sales team powered by conversational AI. Our platform holds natural, one-to-one SMS conversations with people who started a signup but didn't finish - answering their questions, addressing their hesitations, and guiding them to a decision. We operate on a pure performance model and have grown into a profitable, founder-led company growing 6-7x yoy. The opportunity We're hiring our first ft engineer. You'll inherit a working production system that generates all of our revenue, and your mandate is to make it better: smarter conversations, stronger infrastructure, faster experimentation, and a platform that scales with our growth. The work sits at the intersection of engineering and applied AI. Conversational sales is a genuinely hard problem, every conversation is different, tone matters as much as accuracy, and small improvements compound into real revenue. You'll have full ownership, and immediate feedback on everything you ship. The role is forward-deployed in spirit - you work inside the live production system and sales team every day, close to real conversations and real outcomes, not on a roadmap about them. But it's an internal role: no client demos, no external stakeholders. Your users are our own team and the tens of thousands of people we interact with every ady What you'll do Take ownership of our production AI systems and the infrastructure supporting them Improve conversation quality: analyze live performance, diagnose issues, and ship measurable improvements Build evaluation and testing frameworks so changes can be validated quickly and safely Develop internal tooling for experimentation, QA, and client onboarding Evolve the architecture over time while keeping a live system running smoothly Collaborate closely with the founder on priorities and product direction What we're looking for Experience building and running LLM-powered systems in production Solid software engineering fundamentals: APIs, databases, debugging, system design A pragmatic approach, comfortable improving an existing system rather than insisting on a rewrite The ability to evaluate AI output critically and turn observations into effective changes Excellent written English and communication skills Comfort with autonomy and ownership in a small, fast-moving company Working-hours overlap with North American Eastern Time Bonus points Early-stage or founding engineer experience/ you've been the first or only technical hire before Conversational AI, messaging platforms, or marketing/sales automation background Experience with LLM evaluation methods and prompt testing Familiarity with workflow automation tools such as n8n? Exposure to healthcare or consumer/dtc marketing Why join Full ownership of a revenue-critical AI product, without layers of process Work directly with the founder and shape the technical direction of the company Tight feedback loops between your work and business results Stable, profitable company with a remote-first, low-meeting culture $90,000–$120,000 USD depending on experience and location, + performance-based growth How to apply Tell us about an AI or automation system you've operated in production / a problem you uncovered, how you addressed it, and what changed as a result. Include your resume, LinkedIn, or portfolio. Shortlisted candidates complete a paid work sample based on real, anonymized data.