Staff Software Engineer, Full Stack (Member Benefits)

Sidecar Health is redefining health insurance to make healthcare more affordable, accessible, personalized, and transparent. The Staff Software Engineer will own scalable data pipelines, third-party integrations, production APIs, and full-stack internal tools supporting provider, benefit, and pricing data, while setting technical direction and mentoring engineers.

Responsibilities:

• Own and evolve the production services and APIs that power provider, benefit, and pricing experiences for members, partners, and internal teams, including the data flows into Snowflake and out to third-party consumers
• Design, build, and operate third-party integrations as resilient production services (idempotent, retry-safe, and observable), handling schema drift, malformed data, and partner-specific quirks gracefully
• Build full-stack internal products that automate repetitive, high-volume operational work (e.g., pricing adjustments for benefit amounts) — turning manual processes into scalable, self-service applications with clear UX and audit trails
• Ensure the production services handling large volumes of medical provider data meet a high bar for correctness, latency, data quality, and auditability
• Set technical direction for service architecture and integration patterns — evaluate and introduce modern architectural approaches (service-oriented design, API contracts, event-driven systems, workflow orchestration, etc.) where they solve real problems
• Act as a technical unblocker across teams: review designs, pair on hard problems, and help other engineers ship product features rather than stall
• Drive engineering standards for production reliability: SLOs, observability, alerting, testing, and safe deployment practices (feature flags, canary releases, fast rollbacks)
• Take part in and help shape on-call and incident response: lead root-cause analysis and drive the fixes that prevent repeat incidents
• Partner closely with product, operations, and pricing stakeholders to translate ambiguous business needs (like "automate this pricing process") into durable product capabilities and production services
• Mentor engineers and raise the technical bar through code review, design docs, and hands-on collaboration

Requirements:

• MUST BE BASED IN CALIFORNIA, OREGON OR WASHINGTON
• This role is not eligible for sponsorship
• 10+ years of professional software engineering experience, with a track record of owning data-intensive systems in production
• Deep experience building and operating data pipelines at scale; ingestion, transformation, and delivery
• Hands-on experience building and maintaining third-party integrations, including handling unreliable or inconsistent external data
• Experience building internal tools/platforms that automate operational workflows for non-engineering teams
• Strong fundamentals in distributed systems, data modeling, and modern architectural patterns for processing data at scale
• Demonstrated ability to operate as a technical leader: setting direction, unblocking others, and influencing without direct authority
• Comfort with ambiguity; you can take a loosely defined operational pain point and turn it into a well-scoped technical solution
• Strong communication skills; able to explain a data architecture tradeoff to both engineers and non-technical stakeholders
• Fluent, disciplined use of AI-assisted tooling to move faster, with the rigor to verify correctness, security, and quality before it ships
• Snowflake experience strongly preferred
• Experience with healthcare data (provider directories, NPI, claims, fee schedules, or benefits data)
• Familiarity with workflow orchestration tools (Airflow, dbt, Step Functions, etc.)