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Sierra is building a full sales organization with formal compensation infrastructure, a sign it is moving from founder-led deals toward a scaled enterprise sales machine selling AI agents to large brands.
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.
Own all compensation communications to the field: plan launches, plan documents, policy updates, and payout notices. Every message should be clear, accurate, and on time.
Respond to rep questions quickly and within a defined SLA, and track each request through to resolution so nothing falls through the cracks.
Keep the internal sales compensation team aligned on every plan and policy change, and confirm each change is put into practice in calculations, systems, and processes.
Make sure every rep understands how they are paid through plan training, new-hire onboarding, office hours, and enablement tools (earnings calculators, plan summaries, FAQs, and training decks).
Model the cost, payout, and behavior impact of proposed plan designs and changes, and present tradeoffs that help leaders make decisions.
Support the team on the monthly payroll process, including validating payouts, reconciling against plan terms, and preparing the payroll handoff.
5+ years in sales compensation, commissions operations or a closely related finance/RevOps role, with hands-on involvement in at least one full annual plan design cycle.
Experience with plan architecture and pay mix, including target incentives, measures and weightings, accelerators, and how plan design drives seller behavior.
Strong modeling skills: building plan cost models, payout curves, and scenario analyses that leaders can act on.
A track record of rolling out comp plans and changes to sales teams, including writing plan documents, running trainings, and building self-service enablement tools.
Experience supporting a monthly commission payroll cycle, including payout validation, reconciliation, and payroll handoff.
Experience using Salesforce and sales compensation tools to report on attainment and payouts.
Experience designing compensation for new roles or go-to-market motions at a high-growth company.
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.
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