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Sierra is a leading platform for customer-facing AI agents, serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is based in San Francisco with growing offices across North America, Europe, and Asia.
You will design and build a structured onboarding program for new Account Executives and Sales Engineers with role-specific tracks. You'll deliver onboarding through live sessions, asynchronous content, cohort workshops, certifications, and role-plays. A key focus is introducing AI Fluency at Sierra and helping sellers incorporate AI into daily activities like account research, call prep, call recaps, and pipeline updates. You'll ensure every seller can explain, demo, and credibly speak about how Sierra uses AI so they can engage with customers learning to deploy AI themselves.
You will establish baseline ramp metrics (time to first meeting, first deal, quota attainment, SE readiness) and set targets for reducing them. You'll leverage AI tools to scale enablement: faster content creation, AI-driven role-play and call coaching, and self-serve answers to seller questions. You'll partner with Product, Marketing, Sales Leadership, and Sales Engineering to keep content current as the product and market evolve.
You'll recruit subject-matter experts, including top sellers and SEs, to teach and coach in the program. You'll gather feedback from new hires and managers, iterating on the program quarterly. You'll build the global program so it can be adapted for regional teams, including the London office.
REQUIREMENTS:
- 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 hands-on work in early months, not just manage; 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
PREFERRED:
- Experience running sales kickoff or product launch enablement
- Experience selling or supporting sales in AI, SaaS, or enterprise software
- Familiarity with enablement platforms (Highspot, Seismic, Salesforce, Gong)
- Experience running onboarding through rapid headcount growth, or handing a program to a successor
