Strategist, Agent Development - Flagship Deployment
San Francisco, CA, New York, NY$200k - $290kFull-timePosted 4w ago
About the role
Lead end-to-end deployment for large-scale Sierra AI agent deployments with enterprise customers, owning the Agent Development Life Cycle from scope to launch and iteration, and aligning strategic objectives with customer success and financial outcomes.
Responsibilities
- Own the Agent Development Life Cycle: scope, conversation design, tooling, evaluation, launch, and continuous production iteration; translate business goals into high-performing agents.
- Be the trusted strategic advisor to enterprise leaders; understand success metrics and shape AI strategy accordingly.
- Partner with the customer's working teams and executives day to day; oversee program management and long-term roadmap alignment.
- Navigate enterprise complexity with cross-functional teams (engineering and product); manage discussions with procurement, compliance, and senior executives.
- Directly impact product by surfacing unmet needs from customer work to research and platform teams.
- Manage internal resourcing to ensure deployment is adequately staffed today and in the future.
- Drive financial success for both customer and Sierra; optimize value exchange and margins; work to reduce cost to serve over time.
- Partner with Sales on commercial strategy; identify opportunities and align resources to close new business within deployments.
Qualifications
- 10+ years of relevant enterprise customer-facing experience, ideally in a dedicated embedded model with a named enterprise account.
- Customer obsession and ability to thrive in complex organizations; build trusted relationships.
- Clear, direct, and persuasive communication across technical and non-technical audiences.
- Strategic problem-solving in ambiguity with strong analytical and critical-thinking skills.
- Technical aptitude: comfortable engaging with technical concepts, APIs, data models, and system architecture.
- Ownership and delivery track record of running multiple complex, high-visibility projects.
Skills
Required:Enterprise stakeholder managementStrategic problem-solvingTechnical aptitude
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 and snacks/coffee
- Discretionary benefit stipend
- Free alphorn lessons
Last updated Sep 23, 2026. Interested? Apply on the company site.
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
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