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Sierra is a leading platform for customer-facing AI agents, working with major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is headquartered in San Francisco with growing offices across North America, Europe, and Asia. Founded by Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs and AR/VR initiatives), Sierra is transforming how organizations serve customers through AI.
The Healthcare Team focuses on AI agents that reach over 50% of U.S. families, partnering with leading health plans, providers, and healthcare platforms. These agents handle sensitive, high-stakes conversations—helping members understand benefits, resolve billing questions, schedule appointments, and navigate the healthcare system with empathy and strict HIPAA compliance.
In this role, you will:
- Design and deliver production-grade AI agents for healthcare that handle sensitive patient and member interactions while maintaining HIPAA compliance and trust.
- Drive the Agent Development Life Cycle (ADLC) with complete ownership from pilot through deployment and continuous iteration in production environments.
- Partner directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their challenges and build transformative AI solutions.
- Develop deep expertise in healthcare systems and workflows, including EHR integrations, payer/provider operations, benefits eligibility, claims and billing, scheduling, and healthcare data standards.
- Shape the evolution of Sierra's core platform by surfacing unmet needs, prototyping new tools, and collaborating with research, product, and platform teams.
Example projects include building AI agents for major health insurance networks to answer detailed benefits questions, developing voice and chat agents for providers to help members find specialists and schedule appointments, creating conversational intake experiences to replace paper forms, and building agents for healthcare financial platforms to help patients understand billing and financial assistance—all while maintaining HIPAA compliance and PHI/data privacy safeguards.
REQUIREMENTS:
- Experience building and scaling end-to-end production systems
- Strong technical problem-solving skills in fast-changing, ambiguous environments
- Builder and tinkerer's mindset with high agency and creative problem-solving
- Comfort working directly with customers to understand needs and solve real-world problems
- Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences
- Genuine interest in healthcare and improving patient/member experiences
PREFERRED QUALIFICATIONS:
- Experience in healthcare technology, health IT, or working with healthcare organizations
- Familiarity with major EHR ecosystems (Epic, Cerner/Oracle Health, athenahealth), X12 EDI transactions, clearinghouse workflows, scheduling/patient access, practice management, and contact center platforms
- Understanding of healthcare compliance requirements (HIPAA, PHI handling, healthcare data privacy)
- Experience building or deploying AI/LLM systems in production
- Founder or founding engineer background with experience balancing craft, ownership, and speed
- Familiarity with eval frameworks, agent tooling, RAG pipelines, and prompt engineering
- Experience with React, TypeScript, and/or Go
- Prior experience interfacing with customers or leading technical projects with external stakeholders
