Onboarding Lead, Sales Enablement

Sierra•San Francisco, CA

2d•$210,000 - $255,000

About The Position

Sierra is hiring an Onboarding Lead, Sales Enablement to design and build a structured, global onboarding program for Account Executives and Sales Engineers. The program will include role-specific tracks and be delivered through live and asynchronous formats, including cohort sessions, workshops, certifications, and role-plays. The role will introduce Sierra’s concept of AI Fluency and help sellers incorporate AI into everyday sales activities, while ensuring they can credibly explain and demonstrate Sierra’s use of AI to customers. The Onboarding Lead will establish baseline ramp metrics and targets, use AI tools to scale enablement, and keep materials accurate in partnership with Product, Marketing, Sales Leadership, and Sales Engineering. The role will recruit subject-matter experts to teach and coach, collect feedback from new hires and managers, and iterate on the program quarterly. The program should be designed for global adaptation, including regional teams such as the London office. Sierra is primarily an in-person company based in San Francisco, with offices across North America, Europe, and Asia. The company describes its culture through the values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family.

Requirements

At least 6 years of sales enablement experience at a high-growth B2B software company.
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 declining requests based on data.
Track record of connecting enablement work to business outcomes rather than completion rates alone.
Strong facilitation skills and comfort teaching experienced sellers and executives.
Willingness to do hands-on work in the early months and build from scratch with limited process and few resources.
Ability to learn a technical product, such as AI agents or enterprise software, well enough to teach it credibly.
Daily hands-on use of AI tools and experience teaching others to adopt new tools and change how they work.

Nice To Haves

Experience running sales kickoff or product launch enablement.
Experience selling or supporting sales in AI, SaaS, or enterprise software.
Familiarity with enablement platforms such as Highspot, Seismic, Salesforce, or Gong.
Experience running onboarding through rapid headcount growth or handing a program to a successor.

Responsibilities

Design and build a structured onboarding program for new Account Executives and Sales Engineers, with role-specific tracks.
Deliver onboarding through live and asynchronous formats, including cohort sessions, workshops, certifications, and role-plays.
Introduce AI Fluency at Sierra and teach sellers to apply it to daily sales activities such as account research, call preparation, call recaps, and pipeline updates.
Ensure sellers can explain, demonstrate, and credibly represent how Sierra uses AI to customers.
Establish baseline ramp metrics, including time to first meeting, first deal, quota attainment, and Sales Engineer readiness, and set targets to reduce ramp times.
Use AI tools to scale enablement through faster content creation, AI-driven role-play and call coaching, and self-service 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 Sales Engineers, to teach and coach in the program.
Gather feedback from new hires and managers and iterate on the program quarterly.
Build a global program that can be adapted for regional teams, including the London office.

Benefits

Flexible (unlimited) paid time off.
Medical, dental, and vision benefits for employees and their families.
Life insurance and disability benefits.
Retirement plan dependent on country of employment.
Parental leave.
Fertility and family building benefits through Carrot.
Lunch, snacks, and coffee.
Discretionary benefit stipend.
Free alphorn lessons.
Eligible full-time employees can participate in Sierra's equity plans, subject to applicable plans and policies.