Staff Software Engineer, Full Stack (Search)

Sidecar Health is redefining health insurance to make healthcare more affordable, attainable, personalized, and transparent. The Staff Software Engineer will own search end to end, including OpenSearch infrastructure, ingestion pipelines, relevance and ranking, APIs, quality measurement, reporting, and incident response. The role also provides technical leadership across engineering and product while contributing across the stack and using agentic developer tools.

Responsibilities:

• Own our AWS OpenSearch domains: index design, mappings, analyzers, cluster sizing, performance, cost, and upgrades
• Design and evolve our search APIs so that product surfaces can query drugs, practices, and future verticals consistently
• Lead the expansion of search to new content types (labs, imaging centers, and beyond), including the data model and index strategy for each
• Own relevance quality: query understanding, synonyms and terminology handling, typo tolerance, geo-aware ranking, and boosting on quality and cost signals
• Evolve our hybrid search approach, combining lexical and semantic (vector) retrieval in OpenSearch, and decide where embeddings and LLMs do and don't belong in the query path
• Define how we measure search quality (relevance judgments, zero-result rate, click-through, conversion) and build the tooling and experiments to improve it
• Own the pipelines that move data from source systems into OpenSearch, today a combination of batch and streaming, with a roadmap toward near-real-time indexing
• Partner with the teams that own the underlying data on schema, quality, and freshness, and own the triage and feedback loop when search results are wrong or stale
• Instrument pipelines for observability so freshness and correctness issues are caught before members see them
• Be the technical owner and voice for search across engineering, product, and executive stakeholders, tailoring the level of detail to each audience
• Publish search health and quality reporting that leadership can act on
• Write design docs and RFCs, set technical direction, and mentor engineers working on search-adjacent features
• Own incident response for search and drive root-cause fixes
• Use agentic developer tools (e.g., Claude Code, or similar) as a core part of how you work, and build the internal tools search needs: relevance judgment tooling, search analytics dashboards, index management utilities
• Contribute across the stack when needed, understanding how a result travels from index to query to API to the member's screen

Requirements:

• 8+ years of software engineering experience, with significant time spent owning search systems in production
• React and Next.js experience
• Experience with search observability and tooling (OpenSearch Dashboards, custom relevance tooling)
• Background in healthcare data such as provider directories, NPI, drug/formulary data, or fee schedules
• Experience taking a search system from batch to near-real-time indexing