Onboarding Lead, Sales Enablement
- Location
- San Francisco, CA · On-site
- Job type
- Full-time
- Level
- Lead / Staff
- Experience
- 6+ years
- Listed
- 18 days ago
Skills & highlights for this role
- Sales enablement at a high-growth B2B software company
- Hands-on onboarding or training experience
- Cross-functional program management
- Onboarding design for quota-carrying sellers and technical sellers
- Tying enablement work to business outcomes
- Strong facilitation for experienced sellers and executives
- Ability to learn and teach a technical AI agent / enterprise software product
- Daily hands-on use of AI tools and experience teaching adoption
Also useful
- Sales kickoff or product launch enablement
- Selling or supporting sales in AI, SaaS, or enterprise software
- Enablement platforms such as Highspot, Seismic, Salesforce, or Gong
- Running onboarding through rapid headcount growth
- Handing off an enablement program to a successor
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
What We Offer
We want our benefits to reflect our values and offer the following to full-time employees:
- 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 through Carrot
- Lunch, as well as delicious snacks and coffee to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
Be You, with US
- We're working to bring the transformative power of AI to every organization in the world.
- To do so, it is important to us that the diversity of our employees represents the diversity of our customers.
- We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team.
- We encourage you to apply even if your experience doesn't precisely match the job description.
About US
Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands - including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank - to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
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.
- Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
- Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
- Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
- Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
Equal opportunity and legal notices
We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
From Sierra's careers page, first listed on Rolev.ai on October 23, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
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Common questions
Where is the Onboarding Lead, Sales Enablement job at Sierra located?
This Onboarding Lead, Sales Enablement position at Sierra is located in San Francisco, CA (On-site). Always check Sierra's application page for specific state eligibility or relocation policies.
What qualifications are required for Onboarding Lead, Sales Enablement at Sierra?
For the Onboarding Lead, Sales Enablement role, Sierra highlights 6+ years of relevant experience; experience with Sales enablement at a high-growth B2B software company, Hands-on onboarding or training experience, Cross-functional program management, Onboarding design for quota-carrying sellers and technical sellers, Tying enablement work to business outcomes, Strong facilitation for experienced sellers and executives. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Onboarding Lead, Sales Enablement position at Sierra?
This listing links directly to Sierra's Ashby application page. You can apply directly on Sierra's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.