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

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.

• Flexible (unlimited) paid time off

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• Parental leave

• Fertility and family building benefits through Carrot

• Free alphorn lessons