About the role
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, Paris, Madrid, Munich, Singapore, Japan, and Sydney. 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 verticals—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. 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 As a member of our Agent Strategist function at Sierra, you will be responsible for partnering with our Agent Product Managers and Agent Engineers to scope, build, and ship AI agents that handle thousands of customer conversations a day. You’ll play a central role in agent development, combining product strategy, conversational design, and customer insight to bring high-quality agents to life. Be a trusted advisor to our healthcare customers and drive their AI strategies. Build, design and refine conversational AI agents, gaining direct exposure to how these products are developed and improved. Drive execution and delivery of multiple complex, high-visibility agent development projects. Coordinate across technical and non-technical stakeholders through the full agent development lifecycle process. Ensure clear communication across all stakeholders while developing strong relationships. Contribute data-driven, strategic insights to customers and internal team decisions. Design, launch, and optimize HIPAA-compliant agents across complex healthcare workflows. Translate operational healthcare challenges into scalable AI solutions and serve as a trusted advisor on AI strategy. Use frontline insights to improve agent performance and contribute to Sierra’s healthcare roadmap. Example projects These are examples of projects our healthcare team has worked on: Lead the project for building AI agents for major health insurance networks that handle detailed questions like "what's my co-pay for a primary care visit?" and "how many physical therapy sessions do I have left?" Ideate and create a roadmap for growing value for large healthcare payers and providers 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. What you'll bring Outstanding Communication Skills: Excellent verbal and written communication skills to convey complex technical information to non-technical stakeholders, fostering collaboration and driving projects forward with clarity. Technical Expertise: Strong understanding of software development, product management and engineering principles, enabling you to act as a strategic partner to customers and internal teams as we turn visionary ideas into agents. Problem-Solving and Analytical Skills: Strong analytical and critical thinking skills to grasp complex concepts, and to identify risks and issues, develop mitigation strategies, and handle unexpected challenges across customer relationships and products. Leadership and Team Management: Proven ability to manage multiple projects simultaneously, leading and inspiring teams to deliver innovative ideas and exceptional agents. Genuine interest in healthcare and improving patient/member experiences. Experience in healthcare technology, health IT or working with healthcare organizations and an understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) are a strong plus Foundational Expertise: Degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience that demonstrates comparable expertise is a strong plus. MBA or comparable experience at the intersection of technology and operations is another strong 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 (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, 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.