Engineering Manager - Case Strategy Engineering

Pivotal Health is the leading technology platform that helps healthcare providers get paid fairly in an increasingly complex reimbursement landscape. Many providers face persistent underpayment from health insurance companies, despite delivering high-quality care. Pivotal Health combines software, data, and service into a seamlessly integrated, AI-driven platform that simplifies 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.

The Role

We’re looking for an Engineering Manager to lead our Case Strategy Engineering team as we expand one of the most consequential areas of Pivotal’s product. You’ll own the engineering systems that turn data, AI, and machine-learning capabilities into better strategies for offers, IDRE selection, position statements, batching, and other critical decisions across the IDR workflow.

You’ll lead an experienced team of engineers and work closely with our Data Science and AI Platform teams to bring new models into production. The team owns the full engineering layer around those capabilities—including data models, databases, APIs, feedback systems, and full-stack product experiences.

This role reports to the Director of Product Engineering. It is a high-accountability role: the problems are ambiguous and the outcomes directly influence customer lift and annual recurring revenue (ARR). The right person will find that combination energizing.

What You'll Do

• Drive the engineering outcomes that improve the incremental reimbursement Pivotal delivers for customers. Connect the team’s technical roadmap to measurable gains in customer value and ARR.

• Own the data models, databases, APIs, services, and full-stack workflows that apply case strategies throughout the IDR process.

• Work with Science and AI Platform to move AI and ML capabilities from experimentation into reliable, usable product experiences.

• Build the systems that capture outcomes, surface useful signals, and feed real-world results back into model development and strategy improvement.

• Set clear priorities, coach engineers, create accountability, and make sound decisions while preserving rigorous technical debate.

• Hire additional engineers and establish roles, ownership boundaries, and operating practices as the team expands.

• Turn ambiguous product and technical problems into clear plans, sequence the work, manage dependencies, and ensure consistent delivery of meaningful improvements.

• Guide architectural decisions across Python services, GCP infrastructure, data systems, LLM-enabled capabilities, and customer-facing applications.

• Apply AI-enabled development tools to explore ideas, prototype solutions, and contribute directly when it accelerates the team or improves technical decisions.

What We're Looking For

• You have spent several years (7+ as an individual contributor and 2+ as a manager) building and leading engineering teams in early-stage environments where structure, roadmap, and technical approach were still being defined.

• You bring a strong individual-contributor foundation and enough technical depth to guide architecture, evaluate tradeoffs, and earn the trust of experienced engineers.

• You have led the delivery of production AI or ML products, or managed engineering work in close partnership with data-science or applied-science teams.

• You understand how to build reliable systems around models, including data pipelines, feedback loops, APIs, monitoring, and product workflows where model outputs are applied.

• You can lead through ambiguity and imperfect data, forming clear points of view without waiting for every question to be resolved.

• You know how to manage an experienced, opinionated team—creating clarity and making decisions without shutting down productive disagreement.

• You connect engineering work to business and customer outcomes and are prepared to own results tied directly to Pivotal’s most important KPI: ARR.

• You communicate technical decisions with precision and can create alignment across Engineering, Science, Product, and other partners.

Extra Credit Experience

• Experience in healthcare, provider reimbursement, revenue-cycle management, claims, or Independent Dispute Resolution.

• Experience with optimization, experimentation, decision systems, strategy models, or feedback-driven ML products.

• Experience scaling an early engineering team or building production AI systems using Python, GCP, and LLMs.

Why You’ll Love Working Here

We’re a collaborative, low-ego team on a mission to make healthcare reimbursement fairer for providers. We offer competitive compensation, including equity, full health coverage, retirement savings plans, flexible time off, and opportunities for company-wide connection and events.

If you’re excited by solving complex problems and making a real-world impact, we’d love to hear from you.