Enterprise AI agents · San Francisco
At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Japan, and Sydney.
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 Family. 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.
The role
Sierra is hiring its first Global Head of Sales Enablement to build the programs, content, and systems that make a world-class Sales team even better. This person will build an enablement function that is ahead of the curve — designed for the company Sierra is becoming, not just the one it is today.
This is a builder role. There are strong foundations in place: an onboarding program, a sales bootcamp, core pitch materials — but the opportunity is to take everything to the next level. The right person has done this before at scale and is hungry to do it again.
What you'll do
Own onboarding and ramp for all sales roles — building programs that compress time-to-productivity and equip reps to tell Sierra's story credibly from day one
Lead Sierra's sales bootcamp covering the full motion: pitching, discovery, POC management, competitive positioning, pricing, and the AE/SE/agent development partnership
Build a continuous learning system — certifications, coaching programs, role-specific training tracks, and manager enablement — that raises the skill floor across the entire sales team
Develop and maintain the playbooks that define how Sierra sells: prospecting, discovery, multi-threading, POC management, negotiation, and expansion
Build the measurement framework for enablement — ramp time, quota attainment by cohort, win rates, and program utilization — and hold the function accountable to those numbers
Build and lead a team of enablement professionals, and partner closely with RevOps, Sales Comp, and Deal Desk to ensure operational changes always land with the right enablement behind them
What you'll bring
12+ years in sales enablement or GTM productivity at an enterprise B2B software company, with experience running programs at significant scale
Deep understanding of complex enterprise sales motions, including multi-stakeholder cycles with a services or implementation component
Proven ability to build enablement functions, not just run them — you've started from a foundation and built something that lasted and scaled
Strong people leader who attracts great talent, develops it, and creates a team culture that reflects Sierra's values
Exceptional writer and communicator — can craft a crisp playbook and a compelling training session in equal measure
Hungry to build — brings the ownership mindset and energy of someone who wants to leave something behind that didn't exist before they arrived
Even better…
Experience enabling a team selling into Fortune 500 or Fortune 50 accounts
Familiarity with AI-powered enablement tools and content platforms
Experience building vertical or industry-specific enablement programs
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.
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.
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.