Onboarding Lead, Sales Enablement

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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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,