Staff Site Reliability Engineer

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 Site Reliability Engineer to define and strengthen how reliability, scalability, and operational excellence are built into Pivotal’s platform.

This is a senior individual contributor role with broad influence across engineering. You’ll work hands-on with our infrastructure and production systems while setting the technical direction for reliability across the company. You’ll help us evolve from a rapidly growing platform into one that can scale predictably, recover gracefully, and meet the high standards of availability, security, and auditability required in healthcare.

You’ll partner closely with software, data, AI, security, and product teams to design resilient systems, improve observability, reduce operational risk, and make reliability a shared engineering responsibility. You’ll bring the technical depth to solve our most difficult infrastructure challenges and the leadership to establish practices that raise the bar for the entire organization.

If you’re energized by complex distributed systems, greenfield infrastructure work, and the opportunity to shape reliability at a pivotal stage of company growth, this is the role for you.

What You'll Do

• Set Pivotal’s reliability strategy: Define the technical vision and roadmap for reliability, availability, scalability, and operational readiness. Establish clear service-level objectives and help teams make informed tradeoffs between reliability, velocity, and cost.

• Design resilient, scalable infrastructure: Guide and implement improvements to our cloud architecture, deployment systems, networking, compute, storage, and other shared infrastructure. Ensure our systems can scale with increasing product usage, data volume, and workflow complexity.

• Build world-class observability: Develop a cohesive approach to metrics, logs, traces, dashboards, and alerting. Give engineers the visibility they need to understand system behavior, identify emerging issues, and resolve production incidents quickly.

• Improve incident response and resilience: Establish effective incident management, on-call, postmortem, and disaster recovery practices. Lead the response to complex incidents and ensure lessons result in durable improvements to our systems and processes.

• Reduce operational toil through automation: Identify recurring manual work and build systems, tooling, and automation that make operating Pivotal’s platform safer and more efficient. Improve deployment workflows, capacity management, infrastructure provisioning, and production diagnostics.

• Embed reliability across engineering: Partner with software, data, and AI engineers to improve system design, production readiness, and failure handling. Create reusable patterns, tooling, and standards that allow teams to build reliable services without becoming dependent on a centralized operations function.

• Strengthen security and compliance: Work closely with security and compliance stakeholders to protect sensitive healthcare and financial data. Help ensure our infrastructure, access controls, audit trails, and operational practices meet applicable regulatory and customer requirements.

• Provide technical leadership: Serve as a trusted technical partner to senior engineers and engineering leaders. Lead architecture reviews, mentor engineers, clarify complex tradeoffs, and raise the standard for infrastructure and operational engineering across the organization.

Who You Are

• 8+ years of experience in site reliability engineering, infrastructure engineering, platform engineering, or operating large-scale production systems

• Deep knowledge of cloud infrastructure, distributed systems, networking, containers, orchestration, infrastructure as code, and modern deployment practices

• Experience designing, building, and operating highly available systems in a fast-growing production environment

• Strong understanding of observability, service-level objectives, capacity planning, incident management, disaster recovery, and performance engineering; Hands-on and technically credible, with the ability to debug complex issues across application, infrastructure, network, and data layers

• Experienced in creating automation and internal tooling that reduces operational toil and improves developer productivity

• Comfortable influencing architecture and engineering practices across teams without relying on formal authority

• A thoughtful communicator who can translate operational risk and technical tradeoffs for engineering, product, security, and business stakeholders; Pragmatic about balancing reliability, delivery speed, complexity, and cost

• Comfortable operating in ambiguity and building from scratch - you’re energized by greenfield work, not slowed down by it

Extra credit if you have

• Experience operating infrastructure that handles healthcare, financial, or other sensitive and regulated data

• Familiarity with HIPAA, PHI, SOC 2, data privacy, auditability, and security controls

• Experience supporting data-intensive, AI, or machine learning systems in production

• Experience with multi-region architecture, high-volume asynchronous workflows, or complex distributed processing systems

• A track record of introducing SRE practices at an early-stage or high-growth company

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.