Strategist, Agent Development - Retail

Sierra is the leading platform for customer-facing AI agents, working with large brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The Agent Strategist owns how Sierra's AI agents come to life for customers, transforming their most complex, high-stakes problems into agents that measurably move their business. The Retail team partners with retailers across apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology, with a focus on both support and revenue-generating use cases such as product discovery, cart recovery, and win-back campaigns.

Responsibilities

Own how Sierra's AI agents come to life for customers, from first pilot to a production agent handling thousands of conversations a day; Own the Agent Development Life Cycle: take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production; Be the trusted strategic advisor to enterprise leaders, understanding what success means to their business and shaping their AI strategy; Partner with the customer's working teams day to day: run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch; Directly impact product by surfacing unmet needs from customer work and feeding them back to research and platform

Requirements

Customer obsession: genuine energy being in front of customers, understanding their business and needs, thriving in complex organizations, and building trusted relationships; Communication: clear, direct, and persuasive across technical and non-technical audiences; Strategic problem-solving in ambiguity: strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast; Technical aptitude: comfortable engaging directly with technical concepts, reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion; Ownership and delivery: a track record of running multiple complex, high-visibility projects at once and driving them to outcomes; Interest in retail and consumer experiences: experience in e-commerce, retail technology, marketplaces, or consumer brands, and familiarity with commerce and CX stacks (a strong plus)

Nice to have

Experience building or deploying AI/LLM agents in production, including hands-on work with eval frameworks, agent tooling, RAG, and prompt engineering, working closely with technical counterparts; Experience as a founder, founding team member, or operator; Degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience, and/or an MBA or comparable experience at the intersection of technology and business

Benefits

Flexible (unlimited) paid time off; Medical, dental, and vision benefits for you and your family; Life insurance and disability benefits; Retirement plan dependent on country of employment; Parental leave; Fertility and family building benefits through Carrot; Lunch, snacks, and coffee; Discretionary benefit stipend; Free alphorn lessons; Eligible full-time employees can participate in Sierra's equity plans