Onboarding Lead, Sales Enablement

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.

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.

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.

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. 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.