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Salary
$180k – $390k per year
Location
In office (San Francisco, New York)
Seniority
Staff · 8+ years exp
Employment
Full-Time
Overview
Company
Impact
Profile match
Sierra, formerly known as Sierra Trading Post, is a major American off-price retailer operated by The TJX Companies. The company offers a wide selection of discounted activewear, outdoor recreation gear, footwear, apparel, and home goods from top name brands.

About us

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 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

  • 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

  • As a Software Engineer working on Healthcare Interoperability at Sierra, you will design and build the core healthcare integration primitives that enable Sierra agents to safely connect with EHRs and other healthcare systems of record.

  • Own production integrations with systems such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, and other healthcare platforms, including FHIR, HL7, APIs, flat files, and customer-specific integration patterns.

  • Build reusable platform capabilities for healthcare data access, write-back workflows, authentication, authorization, auditability, observability, testing, and deployment across customers.

  • Partner closely with Agent Engineers to help them design and ship healthcare workflows such as appointment scheduling, patient intake, care navigation, CRM updates, clinical task routing, and other read/write agent actions.

  • Serve as a technical SME with customers’ EHR, IT, security, and operations teams, translating complex interoperability requirements into clear implementation plans and durable Sierra platform capabilities.

  • Help define Sierra’s standards for safe healthcare agent actions, including validation, idempotency, permissions, human-in-the-loop review, escalation, and PHI/data privacy safeguards.

What you'll bring

  • 8+ years of hands-on software engineering experience, including experience operating at or above the level of Senior Software Engineer.

  • Deep experience shipping production healthcare integrations under HIPAA, security, privacy, and compliance constraints.

  • Strong technical fluency with healthcare interoperability standards and patterns, including FHIR, HL7, OAuth/SMART-style authorization, patient identity, data mapping, audit logs, and EHR-specific APIs.

  • Experience building integrations with one or more major EHRs or healthcare platforms, such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, or similar systems.

  • Strong product and platform judgment: you know what should become a reusable primitive, what should remain customer-specific, and how to design abstractions that survive real-world healthcare complexity.

  • Comfort working directly with customers, including EHR analysts, security teams, technical executives, and operations leaders, while staying deeply hands-on in the code.

  • Degree in Computer Science or related field, or equivalent professional experience.

Even better...

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

  • 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 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.

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