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Sierra is a leading platform for customer-facing AI agents, serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The healthcare team specifically partners with health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive patient interactions—from benefits education to billing resolution. These agents already reach over 50% of U.S. families.
In this Enterprise Sales Engineer role, you will own the end-to-end technical pre-sales process for strategic healthcare accounts. You will scope customer use cases, articulate business value, design and demo Sierra's platform, lead technical and architecture reviews, and serve as the trusted technical expert throughout the sales cycle. You'll work with deal sizes of $1M+, managing relationships with C-suite executives and technical leaders. You'll decide when to involve Agent Development, Product, Security, Legal, and other Sierra leaders, keeping everyone aligned on customer goals.
Beyond the initial sale, you'll stay engaged through Agent Development handoff, launch, and expansion to new use cases. You'll mentor other sales engineers, set standards for demos and pilots, write playbooks for strategic deals and GTM processes, and share insights from your largest accounts with Product leadership to inform roadmap decisions.
Sierra is primarily in-person, headquartered in San Francisco with growing offices across North America, Europe, and Asia. The company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family. Co-founders include Bret Taylor (Board Chair of OpenAI, former co-CEO of Salesforce, former CTO of Facebook) and Clay Bavor (18 years at Google, led Google Labs and Project Starline).
REQUIREMENTS:
- 7+ years in Sales Engineering, Solutions Engineering, or customer-facing technical sales
- Proven experience leading sales processes with Strategic customers, consistently closing deals of $1M+
- Demonstrated expertise in demo building, presenting, and GTM functions
- Strong relationship-building skills with C-suite executives and technical leaders
- Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams
- Ability to leverage AI tools efficiently in technical sales (discovery, solution design, demo building, proposals) while owning accuracy
- Experience growing accounts post-sale and defining customer roadmaps
- Bachelor's degree or above (Computer Science or related field preferred, or equivalent professional experience)
BONUS:
- Experience translating code, technical logic, and user requirements to product and engineering requirements
- Experience selling technical AI products
