Founding Customer Success Engineer

About Cair Health Backed by Y Combinator, Foundation Capital, Soma Capital, and other amazing investors, Cair Health has raised over $3M to build the agent-operated revenue cycle management platform for healthcare. We're at $1M+ ARR, profitable, and grew 21x last year. Our customers include clinics, MSOs, digital health companies, EHRs, FQHCs, billing companies, and more. Day to day, we work with operations leaders, heads of RCM, billers, and sometimes engineers. But the product itself is deeply technical, and every account eventually needs someone who can configure the system, troubleshoot integrations, or work directly with a customer's engineering team on our APIs and their data flow. About the role We're hiring our first Customer Success Engineer to own the technical relationship with every customer we bring on. Some days you're forward deployed helping a customer through a live issue. Other days you're heads down configuring an account or customizing a setup. Sometimes you're the one guiding a customer's engineers through our API. As our first hire in this function, you'll build the playbooks, tooling, and agents that every future CSE hire inherits. What you'll do Own the technical relationship for a portfolio of customers, from onboarding through ongoing support Debug and resolve issues that span product, integration, and configuration. Escalate to our platform team only when it actually needs them Customize customer setups to fit their revenue cycle workflows Guide customers' engineers and IT teams through our APIs and integrations Get forward deployed when needed: on customer calls, in their systems, solving problems live Write code and build agents/skills to scale yourself. We're agent-operated, so use that same approach internally to automate repetitive customer work Turn customer pain points into clear, prioritized input for product and engineering Build the playbooks and docs for customer success at Cair Required You'll need a CS degree or equivalent hands-on experience and 3+ years in a technical, customer-facing role (solutions engineering, forward deployed engineering, implementation, or technical customer success). Comfortable writing Python (or similar), SQL, and React on the front end Working knowledge of REST APIs Experience with AWS, GCP, Docker, Git, etc. Hands-on experience building or working with AI agents Comfortable with ambiguity, ok jumping between a config change and a live escalation in the same day Strong communicator, can talk to engineers and non-technical operators in the same conversation Nice to have Experience with EHR integrations, claims/billing systems, or healthcare APIs Early-stage startup experience wearing multiple hats Healthcare or RCM background