About this role
Professionals who thrive at the intersection of complex customer needs and technical problem-solving will find a natural home in this role. Sierra builds customer-facing AI agents for major global brands, transforming how companies handle customer service and drive retail revenue.
This strategist position sits on the retail team, where agents handle everything from order management to product discovery and in-store support. The team works directly with enterprise clients to shape AI strategy, manage the complete agent development lifecycle, and translate high-stakes business goals into production systems that scale.
What you will do
- Own the agent development life cycle from initial scope through conversation design, tooling, evaluation, and continuous production iteration.
- Act as a trusted strategic advisor to enterprise leaders, understanding their business goals and shaping their AI strategy.
- Partner day-to-day with customer working teams by running working sessions and troubleshooting issues to keep builds on track.
- Directly impact product development by surfacing unmet customer needs and feeding them back to research and platform teams.
- Design and launch specialized agents including order management assistants, shopping advisors, in-store support voice agents, and outbound campaigns.
What you need
- Demonstrate customer obsession with genuine energy for understanding client needs and building trusted relationships in complex organizations.
- Communicate clearly, directly, and persuasively across both technical and non-technical audiences.
- Apply strategic problem-solving skills in ambiguous environments to break down complex problems and adapt to rapid changes.
- Possess technical aptitude to engage directly with technical concepts such as API documentation, data models, and system architecture.
- Bring a proven track record of running multiple complex, high-visibility projects simultaneously and driving them to successful outcomes.
Nice to have
- Experience in e-commerce, retail technology, marketplaces, or consumer brands with familiarity in commerce and CX stacks.
- Hands-on experience building or deploying AI/LLM agents in production using eval frameworks, agent tooling, RAG, and prompt engineering.
- Background as a founder, founding team member, or operator who balances craft, ownership, and speed.
- A degree in Computer Science, Engineering, Mathematics, a related technical field, or an MBA with experience at the intersection of technology and business.
Benefits
- Flexible (unlimited) paid time off
- Medical, dental
Skills and tech stack
Questions candidates ask
What is the location policy for this role?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
What is the compensation for this position?
The salary ranges from $200K to $290K with offers of equity included.
Who are the founders of Sierra?
The company was co-founded by Bret Taylor, who serves as Board Chair of OpenAI, and Clay Bavor, who previously led Google Labs.