Sierra - Sales Compensation Lead
Requirements
• Deep expertise in sales compensation design and administration at an enterprise B2B software or AI company, across a range of GTM roles and plan types • Strong financial modeling skills; comfortable owning compensation models at the level of precision Finance expects • Genuine design thinking applied to compensation—able to identify when a plan creates unintended incentives and fix it before it hits the field • Clear and direct communicator who can explain compensation mechanics to a sales rep, a CFO, and a new hire in equal measure • Collaborative by nature—this role touches Finance, HR, Legal, and GTM leadership, and success depends on strong relationships across all of them • Comfortable with ambiguity; helps write the playbook rather than waiting for one to exist • Even better… • Experience with outcome-based, usage-based, or consumption pricing models • Experience designing compensation plans across global geographies • Our values • 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. • Trust: • 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. • Customer Obsession: • 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. • Craftsmanship: • 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. • Intensity: • 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. • Family:
Responsibilities
• Own the end-to-end design and annual refresh of compensation plans across Account Executives, Sales Engineers, and other GTM roles, facilitating alignment across GTM Operations, Finance, and HR • Build compensation frameworks from first principles that reflect Sierra's unique commercial model—outcome-based pricing, paid POC conversion, and multi-year enterprise contract structures • Develop and maintain the financial models that project cost and attainment impact of plan design choices before any plan goes to the field • Track in-year compensation performance, identify design gaps and anomalies, and surface insights that inform ongoing plan adjustments • Own compensation policy and documentation—ensuring reps and managers have clarity on how their plans work at all times • Partner with Finance on expense planning and accruals, and with HR on benchmarking, leveling, and the relationship between base and variable compensation
Benefits
• Location • San Francisco, CA • Location Type • Department • OperationsGTM Operations • $215K – $265K • Offers Equity • 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, Tokyo, 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. • 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 • Retirement plan dependent on country of employment • 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 • Be you, with us
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