About us

• At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, France, Singapore, and Japan.

• We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.

• Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

About the Healthcare team

• Healthcare is one of Sierra's fastest-growing industries—our agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.

• Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. We're proud that our work with partners like Sutter Health, Stellarus, and R1 RCM is demonstrating what's possible when conversational AI truly understands context and nuance.

• Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.

What you'll do

• Design and deliver production-grade AI agents for healthcare: You'll build and ship highly performant, reliable, and empathetic AI agents that handle sensitive patient and member interactions. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands.

• Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments serving healthcare payers, providers, and platforms.

• Partner with healthcare leaders: You'll work directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their most pressing challenges - from managing high call volumes to reducing administrative burden and building AI agents that transform how they operate at scale.

• Navigate healthcare complexity: You’ll develop deep expertise in healthcare systems and workflows, including integrations across EHR and patient access platforms, payer and provider operations, and common healthcare data and interoperability standards. You’ll become fluent in the nuances of benefits and eligibility, claims and billing, scheduling and intake, and translate that understanding into exceptional, trustworthy AI experiences.

• Build the future of the platform: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare.

Example projects

These are examples of projects our healthcare team has worked on:

• Build AI agents for major health insurance networks that handle detailed questions such as, "What's my co-pay for a primary care visit?" and "How many physical therapy sessions do I have left?"

• Develop voice and chat agents for healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location;

• Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics;

• Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates;

• Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility - all while maintaining HIPAA compliance and strong PHI/data privacy safeguards.

• Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions;

What you'll bring

• Experience building and scaling end-to-end production systems.

• Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.

• A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.

• Comfort working directly with customers to understand their 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.

Even better...

• Experience in healthcare technology, health IT or working with healthcare organizations

• Familiarity with healthcare systems: Major EHR ecosystems (e.g., Epic, Cerner/Oracle Health, athenahealth); X12 EDI transactions and clearinghouse workflows; scheduling/patient access, practice management, and contact center platforms.

• Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy).

• Experience building or deploying AI/LLM systems in production.

• Have been a founder or founding engineer—you know what it means to balance craft, ownership, and speed.

• Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering.

• Prior experience with React, TypeScript, and/or Go.

• Previous roles where you interfaced with customers or led technical projects with external stakeholders.

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

• Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

• Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.

• Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

• Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

What we offer

We want our benefits to reflect our values and offer the following to full-time employees:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• Retirement Plan (e.g., 401K, pension) with Sierra match

• Parental Leave

• Fertility and family building benefits through Carrot

• Lunch, as well as delicious snacks and coffee to keep you energized

• Discretionary Benefit Stipend giving people the ability to spend where it matters most

• Free alphorn lessons

These benefits are further detailed in Sierra's policies and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

Be you, with us

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Compensation Range: $180K - $390K