Revenue Compensation Analyst

About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role We're looking for a Revenue Compensation Analyst to join our Revenue Operations team. This is a highly visible role at the intersection of Sales, Finance, People, and Revenue Operations that directly impacts how we motivate and reward our go-to-market organization. You'll own the end-to-end administration of our Revenue compensation programs, from monthly commission processing and audits to annual plan implementation, while partnering closely with Revenue Leadership on compensation design, quota modeling, and incentive strategy. This role is ideal for someone who enjoys balancing operational excellence with strategic problem solving. You'll ensure every salesperson is paid accurately and on time while helping shape compensation programs that drive the right behaviors and support the company's growth. Key Responsibilities Own Revenue Compensation Operations Manage the end-to-end commission process, ensuring accurate and timely monthly payouts across all variable compensation plans. Validate commission calculations through detailed audits of Salesforce, compensation systems, and payroll data. Partner with Payroll and Finance to deliver accurate commission payments and support monthly close activities. Administer CaptivateIQ, including participant management, quota uploads, territories, crediting rules, rate tables, and plan configuration. Maintain compensation documentation, plan logic, calculation methodologies, policies, and audit procedures. Partner on Compensation Strategy Partner with Revenue Operations and Revenue Leadership to design, model, and refine sales compensation plans, SPIFFs, accelerators, and incentive programs. Build financial models to evaluate plan economics, quota attainment, payout curves, and cost of compensation. Support annual compensation planning, quota setting, territory planning, and compensation rollouts. Conduct market benchmarking and analyze industry trends to ensure compensation programs remain competitive and effective. Evaluate the effectiveness of current plans and recommend improvements that better align incentives with company objectives. Deliver Insights Through Analytics Develop recurring reporting on attainment, payouts, commission spend, quota performance, and sales productivity. Analyze compensation data to identify trends, risks, and opportunities across segments, roles, and territories. Build scenario models to evaluate changes in compensation plans, quota methodologies, and organizational structure. Partner with Revenue Leadership, Finance, and RevOps to provide recommendations that improve performance and drive business outcomes. Support the Go-to-Market Organization Serve as the primary point of contact for compensation questions from sales managers and individual contributors. Investigate and resolve commission disputes professionally, accurately, and with strong customer service. Manage compensation letters, SPIFF administration, opportunity splits, territory changes, and quota assignments. Ensure new hires, promotions, transfers, and terminations are accurately reflected across compensation systems. Improve Systems & Processes Continuously identify opportunities to automate manual processes and improve data quality. Partner with cross functionally to enhance integrations between Salesforce, commission platforms, HRIS, payroll, and ERP systems. Leverage AI and automation tools to improve reporting, streamline workflows, and reduce administr…