Enterprise AI Strategist — Flagship Deployment Lead

Socket.dev; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Flexible (unlimited) paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan dependent on country

Parental leave

Fertility and family building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is hiring an Agent Strategist to lead end-to-end deployments for one of our largest enterprise customers. You will own how Sierra's AI agents come to life, balancing product work with customer-facing delivery and driving measurable business outcomes.

The role requires 10+ years in enterprise settings, strong customer obsession, communication, and technical aptitude. You'll partner with executives, manage cross-functional teams, and help shape Sierra's product strategy while ensuring

Qualifications

• 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role.
• Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations.
• Clear, direct, and persuasive communication across technical and non-technical audiences.
• Strong analytical and critical-thinking skills to break down complex problems and adapt quickly.
• Comfortable engaging directly with technical concepts and reading API documentation.
• A track record of running multiple complex, high-visibility projects at once and delivering outcomes.

Responsibilities

• Own the Agent Development Life Cycle from initial scope through conversation design, tooling, and evaluation to launch and production iteration.
• Be the trusted strategic advisor to enterprise leaders and align AI strategy with business goals.
• Partner with the customer's working teams and executives to maintain ongoing alignment on roadmaps.
• Navigate enterprise complexity with cross-functional teams including engineering and product.
• Directly impact product by surfacing unmet needs from customer work and feeding back to research and platform.
• Manage internal resourcing to ensure deployment readiness today and in the future.

Skills

Proven track record

Customer obsession

Communication

Strategic problem-solving in ambiguity

Technical aptitude

Ownership and delivery

Job description

Sierra is hiring an Agent Strategist to lead end-to-end deployments for one of our largest enterprise customers. You will own how Sierra's AI agents come to life, balancing product work with customer-facing delivery and driving measurable business outcomes.

The role requires 10+ years in enterprise settings, strong customer obsession, communication, and technical aptitude. You'll partner with executives, manage cross-functional teams, and help shape Sierra's product strategy while ensuring