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Sierra is the 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 leading health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive, high-stakes conversations—from helping members understand benefits to resolving billing questions. Our healthcare agents already reach over 50% of U.S. families.
In this role, you will own the end-to-end technical pre-sales process for strategic healthcare accounts. You'll go deep on a few key accounts, learning each customer's business thoroughly enough to operate as an extension of their team. Your responsibilities include scoping customer use cases, articulating business value, designing and demoing Sierra's platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
You'll coordinate cross-functional resources—bringing in Agent Development, Product, Security, Legal, and Sierra leadership as needed—keeping everyone aligned on customer goals. You'll raise the bar for the SE team by mentoring others, setting standards for demos and pilots, and writing playbooks for strategic deals and GTM processes. Your engagement extends beyond close: you'll stay with accounts through Agent Development handoff, launch, and expansion into new use cases. You'll also share insights from your largest accounts with Product leadership to inform roadmap decisions.
Sierra is primarily in-person, based 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 balance. 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 AR/VR initiatives).
REQUIREMENTS:
- 7+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales
- Proven track record leading the sales process with Strategic customers, consistently closing deals of $1M+
- Demonstrated expertise in demo building, presenting, and GTM functions with customers or clients
- Strong relationship-building skills with prospect stakeholders, including 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 as a regular part of your technical sales motion (discovery prep, solution design, demo and prototype building, technical proposals), with ownership of accuracy
- Experience growing accounts past initial sale and defining customer roadmaps for expansion
- Bachelor's Degree or above (bonus if in Computer Science or related field, or equivalent professional experience)
BONUS QUALIFICATIONS:
- Experience translating code, technical logic, and user requirements to product and engineering requirements
- Prior experience selling a technical AI product
