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, Sal