Enterprise AI Agent Strategy Lead

Sierra; San Francisco (CA); On-site; USD 140,000 - 190,000; Full time

Benefits offered by this job

Unlimited PTO

Medical, dental, and vision benefits

Retirement plan

Parental leave

Lunch and snacks

Job summary

Sierra is building a customer-first AI platform and seeks an Agent Strategist to bring Sierra’s agents to life for large customers. You will own the end-to-end lifecycle of agent development, from scope through conversation design to production release and continuous improvement.

You will advise enterprise leaders, run sessions with customer teams, and ensure the agent strategy aligns with business goals. This role blends product, technology, and customer success with a focus on financial

Qualifications

• Customer obsession and ability to understand customer business needs.
• Clear, direct, persuasive communication across technical and non-technical audiences.
• Strategic problem-solving in ambiguity with analytical thinking.
• Technical aptitude to discuss API documentation and data models.
• Ownership of multiple high-visibility projects delivering outcomes.
• Interest in financial services and improving the end customer experience.
• Experience building or deploying AI/LLM agents in production.
• Founding or operating experience balancing craft, ownership, and speed.
• Degree in CS/Engineering/Math or MBA or equivalent experience.

Responsibilities

• Own the Agent Development Life Cycle from scope to production and iteration.
• Be the trusted strategic advisor to enterprise leaders.
• Partner with customer teams daily to troubleshoot and keep builds on track.
• Directly influence product by feeding back customer needs to research and platform.

Skills

Customer obsession

Communication

Strategic thinking

Technical aptitude

Project ownership

AI/LLM familiarity

Financial services domain

Education

Computer Science or related technical field

MBA or comparable business experience

Tools

Eval frameworks

Agent tooling

Job description

Sierra is building a customer-first AI platform and seeks an Agent Strategist to bring Sierra’s agents to life for large customers. You will own the end-to-end lifecycle of agent development, from scope through conversation design to production release and continuous improvement.

You will advise enterprise leaders, run sessions with customer teams, and ensure the agent strategy aligns with business goals. This role blends product, technology, and customer success with a focus on financial