Strategist, Agent Development - Retail
San Francisco, CA, New York, NY$200k - $290kFull-timePosted 3w ago
About the role
Strategist responsible for end-to-end development of Sierra’s AI agents for retail clients, from scoping and conversation design to production deployment and ongoing optimization, partnering with enterprise leaders and cross-functional teams to drive measurable business outcomes.
Responsibilities
- Own the Agent Development Life Cycle from initial scope through conversation design, tooling, evaluation, launch and continuous iteration in production
- Be the trusted strategic advisor to enterprise leaders; understand success metrics and shape AI strategy accordingly
- Partner with customer’s working teams daily; run sessions, troubleshoot issues, and keep build on track for launch
- Directly impact product by surfacing unmet needs from customer work and feeding them back to research and platform
- Surface unmet needs from customer work, and feed them back to research and platform to shape Sierra’s roadmap
- Launch and manage projects such as order management agents, shopping/recommendation integration, in-store voice agents, booking/payments/outbound agents, marketplace dispute handling, and outbound campaigns (cart recovery, win-back, churn, renewals)
- Study and implement improvements to agents to drive CSAT, containment, revenue generation, and efficiency across channels (voice, SMS)
Qualifications
- Customer obsession with building trusted relationships in complex organizations
- Clear, direct, persuasive communication across technical and non-technical audiences
- Strategic problem-solving in ambiguity with strong analytical and critical-thinking skills
- Technical aptitude to engage with API documentation, data models, system architecture, and engineering tradeoffs
- Ownership and delivery history of multiple complex, high-visibility projects
- Interest in retail and consumer experiences; familiarity with commerce and CX stacks (e.g., commerce platforms, order management systems, contact center software)
- Experience building or deploying AI/LLM agents in production and working with AI tooling is a plus
- Founding/operational experience and technical/business balance is a plus
- Degree in CS/Engineering/Math or equivalent practical experience; MBA or related experience at tech-business intersection is a plus
Skills
Required:Agent development lifecycle managementStrategic advisoryProblem solving in ambiguityTechnical 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, snacks, and coffee
- Discretionary benefit stipend
- Free alphorn lessons
Last updated Sep 30, 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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