Strategist, Agent Development - Travel, Transportation and Hospitality
About this role
The Travel, Transportation and Hospitality team builds customer-facing AI agents for major airlines, hotel chains, and travel companies to transform guest experiences and drive business growth. Managing the agent development life cycle from initial pilot to production deployment, the strategist owns conversation design, tooling, evaluation, and continuous iteration while advising enterprise leaders. Operating within a small and collaborative environment, the strategist collaborates directly with technical counterparts and customer working teams to shape AI strategy and deliver measurable business outcomes.
What you will do
- Manage the complete agent development life cycle from scoping and conversation design to production launch and continuous iteration.
- Serve as a trusted strategic advisor to enterprise executives to align AI capabilities with business goals.
- Collaborate daily with customer working teams to run working sessions and maintain build timelines.
- Troubleshoot agent performance issues and tune systems for optimal real-world outcomes.
- Surface unmet customer needs to internal research and platform teams to guide product evolution.
What you need
- Demonstrate genuine customer obsession through building trusted relationships and understanding complex business needs.
- Communicate clearly and persuasively across both technical and non-technical audiences.
- Apply strong analytical and critical-thinking skills to solve strategic problems in ambiguous environments.
- Show technical aptitude by engaging directly with concepts like API documentation, data models, and system architecture.
- Bring a track record of running multiple complex, high-visibility projects simultaneously and driving them to successful outcomes.
Nice to have
- Experience building or deploying AI/LLM agents in production with evaluation frameworks, agent tooling, RAG, and prompt engineering.
- Background as a founder, founding team member, or operator balancing craft, ownership, and speed.
- A degree in Computer Science, Engineering, Mathematics, a related technical field, or an MBA with equivalent practical experience.
Benefits
- Offers Equity
Skills and tech stack
Questions candidates ask
What is the remote work policy?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
What is the salary range for this role?
The salary range for this position is $200K to $290K, alongside offered equity.
What kind of customers does the team work with?
The Travel, Transportation and Hospitality team supports some of the largest airlines, hotel chains, rental car brands, cruise lines, and travel tech companies in the world.
What is the team culture like?
The team is small and scrappy, supporting each other with deliverables while being guided by core values that include trust, customer obsession, craftsmanship, intensity, and family.