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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 company is headquartered in San Francisco with offices across North America, Europe, and Asia.
As an Agent Strategist on the Travel, Transportation and Hospitality (TTH) team, you will own the complete agent development lifecycle for Sierra's customers — from initial scoping through conversation design, tooling, evaluation, launch, and continuous production iteration. You will translate business goals into agents that measurably move customer outcomes and tune relentlessly for real-world performance.
Key responsibilities include:
- Own the full agent development lifecycle, taking agents from initial scope through conversation design, tooling, and evaluation to launch and continuous iteration in production. You'll have real ownership and autonomy over outcomes.
- Serve as a trusted strategic advisor to enterprise leaders, sitting shoulder-to-shoulder with customer executives to understand what success means to their business and shape the AI strategy to get them there.
- Partner with customer working teams day-to-day, running working sessions, troubleshooting agents as issues arise, and making calls that keep builds on track for launch.
- Directly impact product by surfacing unmet needs from customer work and feeding them back to research and platform teams to shape Sierra's direction.
Recent example projects include: scoping and launching subscription-retention agents that outperform human agents; building commerce agents that troubleshoot devices end-to-end while personalizing recommendations; redesigning conversation flows for regulated financial services interactions; partnering with product on net-new agent architectures using live customers as design partners; and defining evaluation and quality bars that drive measurable weekly outcome lifts.
The TTH team is small and scrappy. Every engineer is product-led; every PM tinkers with prototypes; every strategist can own an agent end-to-end. You'll set the standard for going beyond your role and help build the travel industry of the future.
REQUIREMENTS:
Must-have:
- Customer obsession with genuine energy for being in front of customers, understanding their business and needs, thriving in complex organizations, and building trusted relationships.
- Clear, direct, and persuasive communication across technical and non-technical audiences.
- 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 including reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in design discussions.
- Track record of running multiple complex, high-visibility projects simultaneously and driving them to outcomes.
Highly valued:
- Hands-on experience building or deploying AI/LLM agents in production, with direct familiarity with eval frameworks, agent tooling, RAG, and prompt engineering.
- Founder, founding team member, or operator experience — ability to balance craft, ownership, and speed.
- Degree in Computer Science, Engineering, Mathematics, or related technical field, or equivalent practical experience; MBA or comparable experience at the intersection of technology and business.
