About this role
Professionals who thrive in client-facing environments and possess a strong technical aptitude will enjoy shaping conversational AI systems for major enterprises at Sierra. The team builds a platform for customer-facing AI agents, helping global brands transform how they serve buyers and scale operations. Day-to-day tasks involve managing the full development lifecycle of these agents, serving as a trusted advisor to enterprise leaders, and partnering with customer teams from initial pilot to production launch.
This role exists to bridge the gap between technical execution and business strategy, ensuring that customer challenges translate into effective conversational agents. Candidates should bring a mix of strategic problem-solving skills, direct communication abilities, and an eagerness to engage closely with technology.
What you will do
- Manage the complete agent development lifecycle from initial scope and conversation design to production launch and continuous iteration.
- Advise enterprise leaders by understanding their business objectives and shaping the AI strategy required to achieve them.
- Partner with customer working teams through daily sessions and troubleshooting to keep agent builds on schedule.
- Surface unmet customer requirements and feed them back to research and platform teams to guide product development.
- Scope and launch specialized subscription-retention agents or commerce tools that handle complex, regulated interactions.
- Define evaluation metrics and quality bars to drive measurable performance lifts in agent outcomes over time.
What you need
- Demonstrate customer obsession through a genuine energy for understanding business needs and building trusted relationships.
- Communicate clearly and persuasively across both technical and non-technical stakeholder groups.
- Apply strategic problem-solving skills to navigate ambiguity, break down complex issues, and adapt to fast-moving changes.
- Maintain technical aptitude with the ability to read API documentation, understand data models, and follow engineering tradeoffs.
- Show a proven track record of running multiple complex, high-visibility projects simultaneously and driving them to completion.
Nice to have
- Experience building or deploying AI and LLM agents in production with tools like eval frameworks, agent tooling, RAG, and prompt engineering
- Background as a founder, founding team member, or operator who balances craft, ownership, and speed
- Degree in Computer Science, Engineering, Mathematics, or a related technical field, or an MBA or comparable business experience
Benefits
- Flexible unlimited paid time off
- Medical, dental, and vision benefits for employees and families
- Life insurance and disability benefits
- Parental leave and fertility and family building benefits through Carrot
- Lunch, snacks, and coffee at the office
- Discretionary benefit stipend and free alphorn lessons
Skills and tech stack
Questions candidates ask
What is the work location policy?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. Employees work from these offices rather than remotely.
What compensation is offered for this role?
The position includes a salary ranging from $200K to $290K alongside offers for equity. Eligible full-time employees can participate in company equity plans.
What kind of projects will I work on?
Strategists scope and launch subscription-retention agents for telecommunications companies, set up commerce agents for device troubleshooting, and redesign conversation flows for regulated financial services. You also partner with product teams on net-new agent architectures using live customers as design partners.
What are the core company values?
The company is guided by values of trust, customer obsession, craftsmanship, intensity, and a commitment to balancing family along the way. These principles dictate accountability, empathy, and responsiveness to customers and teammates.