About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

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 a commitment to balancing Family along the way. 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

• Our healthcare 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.

• 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 integrations grounded in real healthcare workflows. Translate customer requirements into clear recommendations on interfaces, data flows, and EHR configuration. Identify assumptions, tradeoffs, and limitations so engineering teams have an actionable implementation plan.

• Resolve customer-specific EHR complexity. Understand how each organization configures and operates its EHR, including scheduling rules, patient identity, permissions, and workflow dependencies. Work with customer analysts, vendor teams, and Sierra engineers to investigate unexpected behavior and resolve integration blockers.

• Guide integration readiness through go-live. Define customer setup requirements, dependencies, and validation criteria. Guide EHR and IT teams through application registration, access provisioning, environment setup, and workflow testing, partnering with engineers to verify that integrations behave as intended.

• Bring EHR expertise to customer discovery. Partner with Sales, Sales Engineering, and Agent Development to assess feasibility, explain integration requirements, and scope achievable projects. Make clear what Sierra supports today and what requires additional configuration or development.

• Shape Sierra’s healthcare integration roadmap. Evaluate vendor capabilities, integration programs, and emerging customer needs. Recommend where to invest, distinguishing reusable platform capabilities from customer-specific configuration and implementation work.

• Make each implementation easier than the last. Turn deployment experience into reference designs, implementation guides, and internal training. Help teams apply proven approaches and recognize when a customer’s requirements call for a different design.

What you'll bring

• 5+ years of experience in healthcare interoperability or EHR implementation, with direct responsibility for designing or delivering integrations at an EHR vendor, health system, healthcare technology company, or implementation consultancy.

• Deep expertise in at least one major EHR ecosystem, such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, or similar systems. You understand its integration options, configuration model, and implementation processes, and can investigate unfamiliar capabilities independently.

• Practical knowledge of patient-access workflows, such as scheduling, registration, or referral management. You can explain how operational rules and customer configuration affect what an integration can do.

• Technical fluency in healthcare integrations. You can read API documentation, interpret requests and responses, and troubleshoot data and configuration issues. You have hands-on experience with relevant approaches such as FHIR, HL7v2, vendor APIs, or file-based exchange, and can explain when to use them.

• A track record of taking third-party integrations through deployment. You have worked through application registration, authentication and permissions, test and production environments, workflow validation, and go-live dependencies.

• Clear communication and independent judgment. You can lead discovery with EHR analysts and operational teams, turn incomplete information into an implementation plan, and explain recommendations to software engineers and business stakeholders. You know when to validate an assumption before committing to an approach.

Even better...

• Epic certifications in areas such as Bridges, Cadence, Prelude, or Interconnect, or comparable expertise in another EHR ecosystem.

• Experience across multiple EHR vendors or health systems, particularly integrating third-party products into patient-access or contact-center workflows.

• Experience using SQL, scripts, or code to investigate integration issues, or working with teams building AI agents for healthcare.

• Hands-on software development experience, including building or extending integrations with EHRs or other healthcare systems.

• Comfortable contributing directly to integration code, including implementing API calls, troubleshooting failures, and writing tests. Experience with TypeScript, Go, or Python is a plus.

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 dependent on country of employment

• 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, may vary by region, 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.