Sales Compensation Lead

About the Company

Sierra is creating a platform to help businesses build better, more human customer experiences with AI. Founded by Bret Taylor and Clay Bavor, the company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family.

Responsibilities

• Own the end-to-end design and annual refresh of compensation plans across GTM roles
• Build compensation frameworks reflecting unique commercial models like outcome-based pricing
• Develop and maintain financial models to project cost and attainment impact
• Track in-year compensation performance and identify design gaps
• Own compensation policy and documentation for clarity across the organization
• Partner with Finance on expense planning and HR on benchmarking and leveling

Requirements

• Deep expertise in sales compensation design at an enterprise B2B software or AI company
• Strong financial modeling skills with high precision
• Ability to apply design thinking to identify and fix unintended incentives
• Clear and direct communication skills for diverse stakeholders
• Collaborative mindset to work across Finance, HR, Legal, and GTM leadership
• Comfort with ambiguity and building playbooks from scratch

Preferred Qualifications

• Experience with outcome-based, usage-based, or consumption pricing models
• Experience designing compensation plans across global geographies

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits
• Life insurance and disability benefits
• Retirement plan
• Parental leave
• Fertility and family building benefits
• Lunch, snacks, and coffee
• Discretionary benefit stipend
• Free alphorn lessons