Sales Compensation Lead

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. The role Sierra is hiring a Sales Compensation expert to own the design, modeling, and administration of compensation programs across the GTM organization. You will build the compensation infrastructure that motivates a world-class sales team and keeps Sierra's incentive structures tightly aligned with how the business creates value. Sierra's commercial model includes outcome-based pricing, a paid POC phase, and multi-year enterprise contracts, each of which creates nuances that standard compensation frameworks don't handle well. You will need to think from first principles about how to structure incentives that drive the right behaviors across a global and growing GTM team, from initial close through POC delivery, expansion, and renewal. What you'll do - 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 What you'll bring - 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 - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessibl