Onboarding Lead, Sales Enablement

The role

You will design and build a structured onboarding program for new Account Executives and Sales Engineers. You will deliver training through cohort sessions, workshops, and certifications while using AI tools to scale enablement.

What you will do

• Design and build a structured onboarding program for new Account Executives and Sales Engineers
• Deliver onboarding live and asynchronously via cohort sessions, workshops, certifications, and role-plays
• Introduce AI Fluency and how to incorporate it into daily sales activities
• Ensure sellers can explain, demo and stand behind how Sierra uses AI
• Establish baseline ramp metrics and set targets for reducing them
• Use AI tools to scale enablement through content creation, role-play and call coaching
• Partner with Product, Marketing, Sales Leadership, and Sales Engineering to keep content accurate
• Recruit subject-matter experts to teach and coach in the program
• Gather feedback from new hires and managers to iterate on the program quarterly
• Build the global program to be adapted for regional teams

Required qualifications

• 6+ years in sales enablement at a high-growth B2B software company
• Hands-on onboarding or training experience
• 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
• Strong facilitator, comfortable teaching experienced sellers and executives
• Willing to do the hands-on work in the early months
• Comfortable building from scratch with limited process and few resources
• Able to learn a technical product well enough to teach it credibly
• Hands-on, daily use of AI tools in your own work
• Experience teaching others to adopt new tools and change how they work

Nice to have

• 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

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits
• Lunch, as well as delicious snacks and coffee when working onsite
• Discretionary benefit stipend
• Free alphorn lessons
• Eligible full-time employees can participate in Sierra's equity plans

About the company

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands. The company is primarily an in-person company based in San Francisco.