AI Agent Strategist — Retail, End-to-End Deployment

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

Benefits offered by this job

Unlimited PTO

Medical, dental, vision benefits

Life insurance

Retirement plan

Parental leave

Fertility benefits

Lunch, snacks, and coffee

Discretionary benefit stipend

Alphorn lessons

Job summary

Sierra is seeking an Agent Strategist to bring Sierra’s AI agents to life for large retailers and brands. You will bridge product, agent-building, and customer-facing work, translating business needs into agents that perform at scale across thousands of conversations daily.

You’ll sit with executives, design strategic approaches, and lead sessions with customer teams to keep projects on track. This role demands strong communication, ownership, and a customer-obsessed mindset.

Qualifications

• Customer obsession with understanding client goals and building trusted relationships.
• Clear, direct and persuasive communication across technical and non-technical audiences.
• Strategic problem-solving in ambiguous environments and fast-changing contexts.
• Technical aptitude to discuss APIs, data models, and system architecture.
• Track record of owning multiple high-visibility projects to outcomes.
• Interest and experience in financial services and improving customer experience.

Responsibilities

• Own the Agent Development Life Cycle from scope to design, tooling, evaluation and production deployment.
• Serve as trusted strategic advisor to enterprise leaders and shape AI strategy.
• Partner with the customer’s teams day-to-day, run sessions, troubleshoot, and keep builds on track.
• Directly influence product by surfacing unmet needs from customer work.

Skills

Customer obsession

Communication

Strategic problem-solving

Technical aptitude

Ownership and delivery

Financial services interest

Education

CS/Engineering/Math degree or equivalent

MBA or related experience

Job description

Sierra is seeking an Agent Strategist to bring Sierra’s AI agents to life for large retailers and brands. You will bridge product, agent-building, and customer-facing work, translating business needs into agents that perform at scale across thousands of conversations daily.

You’ll sit with executives, design strategic approaches, and lead sessions with customer teams to keep projects on track. This role demands strong communication, ownership, and a customer-obsessed mindset.