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

Pivotal Health is investing heavily in AI as a core strategic capability to transform healthcare operations. We are building intelligent systems that automate complex workflows, improve decision-making, and drive measurable business outcomes across the organization.

As a Senior Applied AI/ML Engineer, you will design, build, and improve production AI systems that solve complex healthcare and operational challenges. You will work at the intersection of machine learning, software engineering, product development, and business operations to deliver scalable AI-powered solutions.

This is an applied AI engineering role—not research in isolation. You will own systems end-to-end, from experimentation and model development through deployment, evaluation, monitoring, and continuous improvement. Your work will directly influence critical products, workflows, and business decisions across Pivotal Health.

We are looking for product-oriented engineers who thrive in ambiguous environments, move quickly from ideas to execution, and are excited to build AI systems that create measurable impact. Whether your background is rooted in machine learning engineering, LLM applications, agentic systems, or intelligent workflow automation, success in this role requires strong technical judgment, a bias toward shipping, and a commitment to continuous improvement.

What You'll Do

Own and improve production AI systems. Design, build, deploy, and optimize AI/ML solutions that support critical healthcare products and operational workflows.

Build LLM-powered applications. Develop production systems involving large language models, retrieval, structured generation, tool use, orchestration, and agentic workflows.

Develop intelligent workflow automation. Create AI-powered systems that automate complex, multistep processes and improve the speed, consistency, and quality of operational decision-making.

Own solutions end-to-end. Take projects from problem definition and experimentation through development, deployment, monitoring, and ongoing optimization.

Design evaluation and experimentation frameworks. Create testing methodologies, benchmarks, and feedback loops that improve model quality, system performance, reliability, and business outcomes.

Translate business problems into scalable systems. Partner with product, operations, data, and engineering teams to define success metrics and turn complex requirements into production-ready AI solutions.

Optimize model and workflow behavior. Improve prompts, retrieval strategies, model selection, system logic, and application performance through continuous experimentation.

Build reliable AI infrastructure. Contribute to the architecture, observability, testing, versioning, rollout safety, and operational reliability of AI-powered systems.

Work with complex healthcare data. Build solutions that operate effectively across structured and unstructured information while maintaining high standards for accuracy, privacy, security, and compliance.

Accelerate AI adoption across the organization. Apply AI tools and best practices to improve team productivity and help establish scalable, AI-native ways of working.

Balance speed with rigor. Deliver impactful systems quickly while maintaining high standards for quality, reliability, safety, and maintainability.

Who You Are

• 5–8+ years of experience building software systems in production environments, with a strong track record of owning and delivering complex technical solutions.

• Experience building and operating applied AI, machine learning, LLM-powered, or agentic systems in production.

• Strong software engineering background, particularly with Python and backend systems that support production-scale AI applications.

• Experience designing and interpreting experiments, evaluation frameworks, benchmarks, or performance measurement systems.

• Proven ability to translate complex operational requirements and real-world data into reliable, scalable, and shipped products.

• Understanding of production engineering practices, including testing, monitoring, observability, system reliability, and safe rollouts.

• Product-oriented mindset with the ability to navigate ambiguity, make thoughtful technical decisions, and drive initiatives from concept through deployment.

• Strong communication and collaboration skills, with the ability to partner effectively across engineering, product, data, and operational teams.

Extra Credit Experience

• Experience building AI-powered products in healthcare, insurance, financial services, or another regulated industry.

• Experience working with healthcare data, clinical documentation, insurance claims, or healthcare operational workflows.

• Familiarity with explainable AI and systems where accuracy, transparency, fairness, and defensibility are important.

• Experience with model fine-tuning, embedding models, vector databases, retrieval systems, or AI evaluation platforms.

• Experience building document intelligence, decision-support, workflow automation, or human-in-the-loop AI systems at scale.

This position is not eligible for employer-sponsored work authorization. Applicants must be legally authorized to work in the United States on a permanent basis without the need for current or future visa sponsorship.*

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.