Onboarding Lead, Sales Enablement
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