Staff Engineer, AI Platform at Pivotal Health

ABOUT PIVOTAL HEALTH Pivotal Health is the leading technology platform that helps healthcare providers get paid fairly in an increasingly complex reimbursement landscape. Today, many providers face persistent underpayment from health insurance companies, despite delivering high-quality care. While processes like IDR (Independent Dispute Resolution) were designed to promote fairness, they’re often administrative-heavy, time-consuming, and difficult to navigate without the right tools. Pivotal Health combines software, data, and service into a seamlessly integrated, AI-driven platform that simplifies these complex reimbursement workflows. We help providers efficiently dispute underpaid claims, reduce administrative burden, and recover the reimbursement they’re entitled to; without adding more work to already stretched teams. Our full-service IDR solution is just the starting point. We’re building solutions that enable providers to operate with clarity, control, and confidence across the reimbursement journey. ABOUT THE ROLE We’re hiring a Staff Engineer, AI Platform to build the shared engineering foundations that make AI systems at Pivotal reliable, observable, and easy to adopt across the company. This is a hands-on technical leadership role for someone who wants to build platform infrastructure, not just advise on it. You’ll own key parts of our AI platform surface, including our Agent SDK, AI observability stack, experimentation and evaluation systems, and greenfield internal tooling for MCPs and AI-powered app builders. You’ll report to the Head of AI/ML Engineering and work closely with applied AI, backend, data, product, and operations partners. This role is intentionally designed as a builder-first staff role. Over time, you may help shape and guide a team around these systems, but success in the role does not depend on moving into people management. We see technical leadership and long-term IC growth as first-class paths. Just as important, this role is about helping Pivotal become an AI-first organization. We want someone who is personally excellent at using AI in their own day-to-day work and can turn that instinct into shared workflows, tooling, and habits that raise the company’s overall capability. WHAT YOU’LL DO - Own the evolution of our shared Agent SDK and adjacent developer-facing libraries. - Define the default engineering patterns for agent runtime behavior, tool use, structured outputs, context management, retries, testing, and deployment. - Build the observability layer for AI systems, including tracing, prompt and model version visibility, tool-call telemetry, cost tracking, latency, failure modes, and fallback behavior. - Create practical dashboards, alerts, and operational workflows that let us catch regressions before the business feels them. - Lead the design of our experimentation and evaluation platform for model-backed and agent-backed systems. - Improve how we compare prompts, providers, retrieval strategies, model versions, and workflow designs. - Build greenfield internal tooling that accelerates company-wide AI adoption, especially around MCP-style tools, app-builder patterns, and reusable internal AI primitives. - Help define what great AI-enabled work looks like inside the company by modeling strong usage patterns and turning them into scalable defaults for other teams. - Turn fragile or manual workflows into well-instrumented platform capabilities with good defaults and clear ownership. - Partner with engineers and product teams to identify the highest-leverage shared investments, then drive them from design through production. - Raise the technical bar through architecture work, design reviews, implementation, mentoring, and strong engineering judgment. WHAT SUCCESS LOOKS LIKE In the first 6 to 12 months, strong outcomes in this role would include: - a clearly adopted internal Agent SDK with defaults, documentation, and developer ergonomics - standardized tracing and observability across AI workflows - a lightweight but real release process for model and prompt changes - stronger experiment and regression tooling for both statistical ML systems and agent workflows - less notebook- and runbook-driven operational work - new internal platform capabilities that make it meaningfully easier for teams across the company to adopt AI safely WHO YOU ARE - You are a strong software engineer first, with staff-level judgment and a track record of owning technical systems that multiple teams rely on. - You have deep experience building platform, infrastructure, or developer tooling, ideally in environments where reliability and usability both matter. - You have experience with AI or ML platform problems such as agent runtimes, LLM tooling, inference infrastructure, experimentation systems, evaluation frameworks, or model observability. - You know how to design APIs, SDKs, and reusable abstractions that improve developer velocity without hiding important complexity. - You are an AI power user yourself. You actively use AI to accelerate engineering work, investigation, debugging, design, and knowledge work, and you have strong judgment about where it helps and where it does not. - You are comfortable operating in ambiguous, greenfield areas and can make pragmatic scope decisions without overbuilding. - You can work cross-functionally and lead through influence, clarity, and execution rather than title alone. - You enjoy being close to the code and architecture, even when operating at broad technical scope. WE’D BE ESPECIALLY EXCITED IF YOU HAVE - strong Python experience in production systems - experience with FastAPI or similar backend frameworks - experience with GCP or comparable cloud infrastructure - experience with LLM platforms, agent frameworks, or prompt/version management systems - experience with experimentation, evals, A/B testing, or statistical decision systems - experience with observability stacks such as OpenTelemetry, Langfuse, LangSmith, Braintrust, Helicone, Datadog, Grafana, or similar tooling - experience building internal developer platforms, workflow platforms, or reusable application scaffolding - experience in healthcare, payments, or other operationally complex domains where software quality directly affects business outcomes WHY THIS ROLE IS INTERESTING - The problems are real, not speculative. You’ll be working on AI systems that sit in important operational workflows, not side experiments. - The scope is unusually high leverage. Success here improves how multiple teams across the company build and ship. - The platform surface is real, but still early. You’ll have the chance to define the right foundations before the architecture calcifies. - The role sits close to product and outcomes. You won’t be building platform in a vacuum. - You’ll help shape how the company actually works. Part of the job is making Pivotal much better at using AI across functions, not just building backend systems in isolation. - You can stay deeply technical. If you eventually want to help build a team around this area, great. If you want to remain a staff-level technical leader, that is equally valuable. WHY YOU’LL LOVE WORKING HERE We’re a collaborative, low-ego team on a mission to make healthcare reimbursement fairer for providers. While we primarily hire around our core hubs–Los Angeles and New York–we remain open to exceptional talent outside those regions. Remote and hybrid flexibility varies by role and team, and is outlined in each job description. If you’re excited by solving complex problems and making a real-world impact, we’d love to hear from you. Benefits Include: - Competitive compensation, including equity - Full health, dental, and vision coverage - Retirement savings plan through 401(k) - Flexible time off - Opportunities for company-wide connection and events Ready to Make an Impact? We’re building something meaningful; and we want you on the team. Bring your ideas, curiosity, and drive, and let’s transform healthcare reimbursement together. EMPLOYMENT INFORMATION Work Authorization Candidates must be authorized to work in the United States without current or future employer sponsorship. Equal Employment Opportunity Pivotal Health is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status. Reasonable Accommodations Pivotal Health provides reasonable accommodations for qualified individuals with disabilities in accordance with applicable laws. If you need assistance during the application or interview process, please let us know. Background Checks Employment is contingent upon successful completion of applicable background checks, where permitted by law. At-Will Employment Employment with Pivotal Health is at-will and may be terminated by either party at any time, with or without cause or notice, in accordance with applicable law.