Enterprise Sales Engineer, Healthcare

About the role

You will own the end-to-end technical pre-sales process for healthcare customers, translating complex business problems into clear demonstrations of Sierra's AI platform and defining viable solution architectures. You will act as the primary technical advisor during sensitive, high-stakes conversations with health plans, providers, and diagnostics companies, ensuring our agents address the most critical patient interactions with empathy and precision. You will collaborate directly with Product and Agent Engineering to capture customer feedback and drive iterative improvements that keep our solutions industry-leading. You will establish yourself as a trusted GTM leader by anticipating client needs and articulating the business value of AI-driven automation in accessible terms. You will explain technical concepts to both technical architects and executive stakeholders, aligning Sierra's capabilities with strategic priorities in healthcare. You will leverage your experience in demo building and solution design to de-risk adoption and accelerate enterprise decision-making. By representing Sierra in key technical reviews and architecture sessions, you will help shape the future of human-centered AI in a regulated industry.

Key facts

What you'll do

• Conduct discovery sessions to scope complex healthcare use cases and define the technical boundaries of AI agent implementations.
• Build and deliver tailored demos that highlight Sierra's platform capabilities, focusing on compliance, security, and patient empathy for healthcare stakeholders.
• Lead architecture reviews with technical leaders, outlining integration patterns, data flows, and risk mitigation strategies for health systems.
• Partner with Sales to develop compelling value propositions that connect clinical and operational problems to measurable AI outcomes.
• Act as the central technical resource for our healthcare customers, providing clarity on platform limitations, roadmap alignment, and implementation feasibility.
• Work alongside Product and Agent Engineering to translate real-world customer interactions into actionable product requirements and improvements.
• Support enterprise-wide sales cycles by creating technical narratives that resonate with CFOs, CIOs, clinical directors, and compliance officers.
• Document solution designs and proof-of-concept results to build repeatable playbooks for scaling AI across care settings.
• Represent Sierra at customer workshops and executive briefings, ensuring consistent messaging around trust, safety, and regulatory considerations.
• Continuously refine your own expertise by studying healthcare regulations, interoperability standards, and emerging AI applications in patient care.

Requirements

• Hold 5-7+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales within enterprise or regulated environments.
• Demonstrate a proven track record in demo building, client presentations, and managing complex technical sales cycles.
• Show a history of relationship-building with executive and technical leaders in healthcare or similarly regulated sectors.
• Bring experience leading sales processes for Enterprise customers, including scoping, discovery, and solution validation.
• Possess the ability to connect specific business challenges to Sierra's AI solutions and communicate effectively with both technical and non-technical audiences.
• Hold a Bachelor's Degree or higher; preference for degrees in Computer Science or related fields, or equivalent professional experience.
• Have hands-on experience working with modern, highly technical industries where AI, automation, or data interoperability are central to the value proposition.
• Show skill in translating code, technical logic, and user requirements into clear product and engineering requirements for cross-functional teams.
• Exhibit strong written and verbal communication skills, with the capacity to distill complex workflows into actionable insights for diverse stakeholders.
• Maintain a high standard of professionalism, reliability, and discretion when handling confidential patient information and sensitive business data.

Nice to have

• Prior experience with AI-related technologies or work in a similarly modern and technically advanced industry.
• Background in healthcare, insurance, or another regulated industry where compliance and trust are critical.
• Familiarity with healthcare data standards, interoperability frameworks, or patient engagement platforms.
• Experience aligning technical solutions with clinical workflows and operational constraints.
• Track record of influencing C-level stakeholders through thought leadership and data-driven storytelling.

Practical notes

• Full-time position based in San Francisco, CA.
• Candidates must be eligible to work in the United States without sponsorship for this role.
• Travel may be required to meet with enterprise customers and attend industry events as needed.
• Applicants must submit all required materials by the deadlines published on our internal hiring portal.