Sales Compensation Lead
About The Position
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.
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
Nice To Haves
- Experience with outcome-based, usage-based, or consumption pricing models
- Experience designing compensation plans across global geographies
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
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
