Senior Engineer

About the Role

Dearest Care is scaling rapidly, and we need a robust technical foundation to deliver consistently exceptional patient and customer experiences. We’re searching for a senior, hands-on engineer who thrives on owning problems end to end — from scoping and designing, through building and shipping, across our full-stack platform. This is a greenfield platform with real adoption. You’ll set architecture, engineering patterns, and development velocity from day one.

Expect to ship quickly alongside intelligent agents, integrate AI directly into the product, build features with healthcare compliance as a core requirement, and collaborate directly with operations and product teams in ambiguous, fast-moving environments. You’ll code alongside our CTO. This isn’t a "sit behind dashboards and guess what matters" role. You’ll talk to advocates and patients, use the product yourself, and ship code that has tangible impact: reducing hospitalizations, ER visits, and chaos for families.

About Dearest Care

Dearest Care was started after our founders' personal journeys navigating the healthcare system for their families. Our vision: everyone deserves a fighter. We blend intelligent software with human advocates, supporting Medicare patients through diagnoses, billing, and care plans. Our mission is supported by investors from Omada, Oscar, and UnitedHealthcare, and guided by a stellar advisory panel with deep expertise in healthcare and technology.

We’re a Series A company operating with a lean, impact-driven mindset, rapid execution, and conscious leadership. Our team is tight-knit and fast-moving, focused on meaningfully improving healthcare navigation.

Responsibilities

• Build and own end-to-end features on a greenfield platform, from design to deployment.
• Set architecture, engineering patterns, and development velocity for the team.
• Integrate AI into the product to drive compliant, operational value in production.
• Develop secure, HIPAA-compliant systems for healthcare applications.
• Collaborate with operations and product teams in high-ambiguity, high-velocity environments.
• Work on the following key projects within your first year:
  • Advocate Workspace (North Star): A comprehensive UI for advocates, featuring a unified inbox (across voice, SMS, email, and video), "Today's Queue" with AI-ranked tasks and risks, and Patient 360 with full health histories.
  • Voice → Actions Engine: From call recording and transcription to automatic task/SOAP note creation, work routing, and safety loops that catch unresolved tasks before readmissions occur.
  • Docu Agent & Billing Rails: Turning time logs and transcripts into clean, compliant CPT/G-codes, building audit trails and explainable workflows. Goal: automate >80% of billing.
  • Chronic Condition Journeys: Disease-specific flows (e.g., Diabetes, CHF, COPD) built into the product, with dashboards proving impact such as "25% fewer readmissions" for specific patient cohorts.
  • Security & Compliance Infrastructure: HIPAA-grade logging, RBAC, consent management, and PHI-safe communications, architected for current direct-to-consumer (D2C) and future B2B use cases.

Requirements

• 5+ years of full-stack development experience with the ability to independently ship complete features — ideally in Python/Django, React/Next.js, and Postgres.
• Own problems, not just code. Take responsibility for features from design through to deployment and value impact over just merging code.
• AI-native mindset: build and ship fast with agent workflows and balance trust and validation for AI output.
• Experience building secure, HIPAA-compliant systems in a regulated healthcare environment.
• Comfortable working with RESTful APIs, relational databases, cloud hosting, and managing CI/CD and deployments.
• Prefer speaking with users over guessing from tickets and measure impact by real outcomes for patients.
• Thrive in high-ambiguity, high-velocity environments.

Nice to Have

• Experience with EHRs, claims systems, or care coordination tools.
• Deep DevOps skills: container orchestration, observability, and security hardening.
• Been among the first five engineers at an early-stage startup.

What Success Looks Like

In 12 months:

• You take full ownership of a major domain (within 45 days) and lead a cross-functional initiative to measurable patient outcome improvements.
• The tools you build let our ops team handle far greater scale efficiently.
• Early technical decisions are enabling fast iteration, not creating bottlenecks.
• You’ve set robust patterns for others to build upon, with a strong compliance and security track record.

Benefits

• Freedom to Build: Own projects completely, from architecture to release. Genuine greenfield ownership with meaningful traction.
• Direct Customer Impact: Your work immediately affects patients, care teams, and partners.
• Entrepreneurial Team: Everyone here has started companies. If you plan to launch your own someday, you’ll learn from the best.
• High-Impact Mission: We’re working to close a $25B+ healthcare navigation gap, with support from leading payers and investors.
• Ownership: High visibility, real autonomy, and a founding equity package.

Pay

Competitive salary + high equity.

Our Vision & Culture

We're building a future where every American has access to a personal healthcare navigator, democratizing access for those contending with chronic illness or healthcare complexity. Our distributed, Americas-based team values diverse perspectives, operational excellence, and delivering truly impactful products.

Our values:

• Human Connection: We foster healthy, supportive relationships—both in our product and on our team.
• Playful Creativity: We bring fun and levity to our work.
• Excellence: In execution, thinking, writing, and communication.
• Radical Candor: Addressing hard issues head-on and uplifting each other.
• Smart Hustle: Competing for our customers with impact, not just effort.
• Conscious Leadership: Guided by the 15 commitments to conscious leadership.

Our story.