Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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!
About the Role
This is a high-impact individual contributor role on our platform team, building large-scale data pipelines and distributed systems that power Sidecar Health's core product. You'll take full ownership of complex, ambiguous problems from architecture through production — designing, shipping, and running the systems you build. If you're a strong senior engineer who thrives on end-to-end ownership and wants your work to matter in healthcare, this is the role for you.
**MUST BE BASED IN CALIFORNIA**
What You'll Do
- Design and own high-throughput, distributed data pipelines and platform infrastructure from concept through production
- Decompose large, ambiguous initiatives into structured, executable plans that the team can move on in parallel
- Write production-grade Python — strongly typed, well-structured, and built to last — not scripts or notebooks
- Optimize SQL at scale: query tuning, data modeling, and understanding execution plans
- Architect across boundaries — defining contracts between frontend, backend services, and infrastructure
- Be a technical resource and mentor for junior engineers, and partner directly with leadership on roadmap and technical decisions
- Instrument systems for observability — knowing what to monitor, not just how to read a dashboard
What You'll Bring
- 5+ years of professional software engineering experience with full ownership of production systems
- Strong proficiency in Python (mypy, Pydantic, proper abstractions) and SQL at scale
- Deep experience building and operating distributed data pipelines and event-driven architectures
- Hands-on AWS experience: Lambda, SQS, IAM, CloudWatch, and cost-aware design
- Docker as a first-class practice
- Habitual, fluent use of AI tools (Claude, Cursor, etc.) as part of your daily workflow
- Observability experience with Datadog or equivalent
- Familiarity with FastAPI, Django, SQLAlchemy, Celery, or Infrastructure-as-Code (Terraform, CDK) is a strong plus
- Bachelor's or Master's degree in Computer Science, Information Systems, or a related field
The Reality
This is a startup. We move fast. We prioritize impact over polish. We expect:
- Bias for action — ship, learn, iterate
- Ownership — you design it, build it, run it
- Pragmatism — solve real problems, not theoretical ones
- Resilience — ambiguity comes with the territory
Healthcare is complex and broken. The work matters.
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.
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
- Must be based in California
- 5+ years professional software engineering experience with full ownership of production systems
- Strong proficiency in Python (mypy, Pydantic, proper abstractions)
- Strong proficiency in SQL at scale (query tuning, data modeling, execution plans)
- Deep experience building and operating distributed data pipelines and event-driven architectures
- Hands-on AWS experience: Lambda, SQS, IAM, CloudWatch, and cost-aware design
- Docker as a first-class practice
- Habitual, fluent use of AI tools (e.g., Claude, Cursor) in daily workflow
- Observability experience with Datadog or equivalent
- Familiarity with FastAPI, Django, SQLAlchemy, Celery, or Infrastructure-as-Code (Terraform, CDK)
- Bachelor's or Master's degree in Computer Science, Information Systems, or related field
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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