GTM Operations, Planning

ABOUT US 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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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 - Own our GTM planning processes end-to-end, including annual and quarterly planning, quota and target setting, and capacity and headcount planning across the go-to-market organization. - Partner with GTM and Finance leadership to develop revenue forecasts, performance goals, and resource allocation plans that support company growth objectives. - Own sales compensation and incentive programs, including plan design, administration, and quota setting. - Deliver actionable GTM performance insights by identifying key business drivers, opportunities, and risks, and translating them into recommendations that improve efficiency, productivity, and execution. - Serve as a strategic partner to GTM, Finance, and Operations leadership, driving cross-functional alignment on goals, building stakeholder buy-in, and enabling effective decision-making and execution across the organization. WHAT YOU’LL BRING - 5–8 years of experience: background in private equity, venture capital, investment banking, or consulting, plus business planning or strategic finance experience at a high-growth technology company. - Exceptional financial modeling and analytical skills, with a demonstrated ability to build forecasts, evaluate business performance, and translate complex data into actionable recommendations. - Experience owning or supporting annual planning, revenue forecasting, sales compensation, or other business planning processes. - Strong executive communication and stakeholder management skills, with a track record of influencing decisions and building alignment across senior cross-functional stakeholders. - A highly structured, detail-oriented problem solver who can navigate ambiguity, independently drive initiatives, and balance analytical rigor with practical business judgment. EVEN BETTER... - SQL proficiency and experience with BI tools such as Hex, Tableau, or similar analytics platforms. - Prior ownership of GTM planning processes, including sales compensation and quotas. - Previous startup or 0 to 1 operational experience in a high-growth AI or SaaS environment. 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.