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.
Skills Required
- 8+ years of software engineering experience
- Significant experience owning search systems in production
- Must reside in California
- React experience
- Next.js experience
- Experience with search observability and tooling, including OpenSearch Dashboards or custom relevance tooling
- Healthcare data experience, such as provider directories, NPI, drug or formulary data, or fee schedules
- Experience transitioning search indexing from batch to near-real-time
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
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Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
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Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
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Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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