Staff Software Engineer, Full Stack (Search)

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

Must reside in California for consideration

About the Role

Search is how our members find care. Every day, members use Sidecar Health to search for drugs and medical practices, compare options, and make decisions about their health and their money. As we expand into new verticals like labs and imaging centers, search becomes even more central to the member experience.

We're hiring a Staff Software Engineer to own search at Sidecar Health end to end: the OpenSearch clusters, the ingestion pipelines that feed them, the relevance and ranking logic, the APIs that serve results, and the reporting that tells the business how well search is working. You'll be embedded in the Member Experience engineering team, and you'll be the person the company turns to for every decision about search.

This is a hands-on role for a search specialist. You know Elasticsearch/OpenSearch deeply, you've tuned relevance in production, and you can explain a ranking tradeoff to an executive as clearly as you can to an engineer.

What You'll Do

Own search architecture and implementation

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

Drive relevance and ranking

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

Build and modernize search data pipelines

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

Communicate and lead

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

Ship with agentic tools

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

What You'll Bring

8+ years of software engineering experience, with significant time spent owning search systems in production

Nice to have

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. This is not required; we'll teach you the domain.

Experience taking a search system from batch to near-real-time indexing

What You'll Get

Competitive salary, bonus opportunity, and equity package

Comprehensive Medical, Dental, and Vision benefits

A 401k retirement plan

Paid vacation and company holidays

Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $200,000 - $240,000. Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.