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Strategist, Agent Development - Healthcare

Sierra· Product
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San Francisco, CA, New York, NY$200k - $290kFull-timePosted 3w ago

About the role

Strategist responsible for end-to-end Agent Development life cycle within Sierra’s Healthcare team, partnering with enterprise customers to translate business goals into production AI agents and drive high-impact outcomes.

Responsibilities

  • Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world.
  • Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
  • Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
  • Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.

Qualifications

  • Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
  • Communication. Clear, direct, and persuasive across technical and non-technical audiences.
  • Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
  • Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
  • Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
  • 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.

Skills

Required:Agent Development Life CycleStrategic advisoryCustomer relationship management
Nice to have:Healthcare domain knowledge

Benefits

  • 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
  • Free alphorn lessons
Last updated Sep 30, 2026. Interested? Apply on the company site.
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About Sierra

Better customer experiences. Built on Sierra.

Sierra helps businesses build better, more human customer experiences with AI.

AICustomer ExperienceCustomer SupportVoiceai-agents-and-applicationsorchestrationvoice-ai-stackwing-list-2026
Company profileWebsite

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