About this role
Enterprises struggle to turn customer-facing AI pilots into production agents that handle thousands of daily conversations without losing accuracy or falling short of business goals. This role solves that challenge by guiding customer deployments from the initial scope through conversation design, tooling, evaluation, and continuous iteration.
Working at the intersection of product development and direct customer engagement, this strategist takes full ownership of the agent development life cycle. Responsibilities involve serving as a trusted advisor to enterprise leaders, running working sessions, and feeding unmet user needs directly back to research and platform teams. The ideal candidate blends technical aptitude with strong commercial instincts, thriving in ambiguous situations and maintaining a genuine energy for direct customer interaction.
What you will do
- Manage the complete agent development life cycle from initial scoping and conversation design to production launch and continuous iteration.
- Act as a trusted strategic advisor to enterprise leaders by aligning AI initiatives with core business goals.
- Partner day-to-day with customer working teams through collaborative sessions, troubleshooting, and execution.
- Surface unmet customer needs from deployments and feed those insights back to research and platform teams.
- Define evaluation metrics and quality bars to drive measurable outcome improvements week over week.
What you need
- Demonstrated customer obsession through genuine energy for understanding user needs and building trusted relationships within complex organizations.
- Clear, direct, and persuasive communication skills across both technical and non-technical audiences.
- Strong strategic problem-solving abilities in ambiguous environments to break down complex issues and spot risks early.
- Technical aptitude including comfort reading API documentation, understanding data models, and following system architecture discussions.
- Proven track record of ownership and delivery in running multiple complex, high-visibility projects concurrently.
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.
- Degree in Computer Science, Engineering, Mathematics, a related technical field, or an MBA with equivalent practical experience.
Benefits
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for employees and families
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave and fertility/family building benefits through Carrot
- Discretionary benefit stipend and office perks including lunch, snacks, coffee, and free alphorn lessons
Skills and tech stack
Questions candidates ask
What is the compensation and equity structure?
The position offers a salary range of £150K to £245K alongside equity opportunities. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of applicable policies.
Where is the company located?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia including London.
What kind of projects will I work on?
Strategists work on projects like scoping subscription-retention agents for telecommunications companies, standing up end-to-end troubleshooting commerce agents, and redesigning financial services conversation flows for regulated interactions.
What are the core company values?
The company culture is guided by trust, customer obsession, craftsmanship, intensity, and a commitment to balancing family along the way.