Strategist, Agent Development – Flagship Deployment

About the role

As an Agent Strategist on a Flagship Deployment, you will own the end‑to‑end delivery of Sierra’s AI agents for one of its largest enterprise customers. You will translate high‑stakes business problems into AI‑driven solutions, working closely with both product and engineering teams while acting as a trusted advisor to senior customer executives.

Key responsibilities

• Own the full Agent Development Life Cycle from scope definition through design, tooling, evaluation, launch and continuous iteration.
• Serve as the strategic advisor to enterprise leaders, shaping AI strategy and ensuring alignment with business outcomes.
• Manage cross‑functional teams—including engineering, product, procurement, and compliance—to navigate technical and commercial negotiations.
• Drive financial success by optimizing value exchange, increasing revenue upside for Sierra, and improving margins.
• Partner with Sales on commercial strategy and identify new business opportunities within the deployment.

Required profile

• 10+ years of enterprise‑facing experience delivering high‑impact results, preferably in an embedded account model.
• Strong customer obsession with a proven ability to build trusted relationships at the executive level.
• Excellent communication skills, able to convey complex technical concepts to both technical and non‑technical audiences.
• Demonstrated ownership and delivery of multiple high‑visibility projects simultaneously.
• Experience leading or managing business units, forward‑deployed teams, or comparable general‑management responsibilities.

Required skills

• API documentation
• Data models
• System architecture
• Evaluation frameworks
• Agent tooling
• RAG (Retrieval‑Augmented Generation)
• Prompt engineering

What we offer

• Unlimited paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance, disability coverage, and retirement plan
• Parental leave and fertility/family‑building benefits
• Flexible, in‑person work environment based in San Francisco