About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

What you’ll do

Design and build a structured onboarding program for new Account Executives and Sales Engineers, with role-specific tracks

Deliver onboarding live and asynchronously: cohort sessions, workshops, certifications, and role-plays

Introduce what AI Fluency means at Sierra and how to incorporate it into daily sales activities (account research, call prep, call recaps, pipeline updates, etc.)

Make sure every seller can explain, demo and stand behind how Sierra uses AI, so they can speak credibly with customers who are learning to deploy AI themselves

Establish baseline ramp metrics (time to first meeting, first deal, quota attainment, SE readiness) and set targets for reducing them

Use AI tools to scale enablement itself: faster content creation, AI-driven role-play and call coaching, and self-serve answers to seller questions

Partner with Product, Marketing, Sales Leadership, and Sales Engineering to keep content accurate as the product and market change

Recruit subject-matter experts, including top sellers and SEs, to teach and coach in the program

Gather feedback from new hires and managers, and iterate on the program quarterly

Build the global program so it can be adapted for regional teams, including our London office

What you’ll bring

6+ years in sales enablement at a high-growth B2B software company, with hands-on onboarding or training experience and experience managing cross-functional programs

Experience designing and delivering onboarding for both quota-carrying sellers and technical sellers

Track record of prioritizing competing requests from senior stakeholders and saying no with data

Track record of tying enablement work to business outcomes, not just completion rates

Strong facilitator, comfortable teaching experienced sellers and executives

Willing to do the hands-on work in the early months, not just manage it, and comfortable building from scratch with limited process and few resources

Able to learn a technical product ([AI agents / enterprise software]) well enough to teach it credibly

Hands-on, daily use of AI tools in your own work, and experience teaching others to adopt new tools and change how they work

Even better…

Experience running sales kickoff or product launch enablement

Experience selling or supporting sales in AI, SaaS, or enterprise software

Familiarity with enablement platforms (e.g., [Highspot, Seismic, Salesforce, Gong])

Experience running onboarding through rapid headcount growth, or handing a program to a successor

Our values

Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.