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Tailscale is seeking a Revenue Operations Analyst to join its Revenue Operations team. This role sits at the intersection of Sales, Finance, People, and Revenue Operations, directly impacting how the company motivates and rewards its go-to-market organization.
You will own the end-to-end administration of Tailscale's revenue compensation programs, managing monthly commission processing, audits, and annual plan implementation while partnering closely with Revenue Leadership on compensation design, quota modeling, and incentive strategy.
Key responsibilities include:
**Revenue Compensation Operations**: Manage the complete 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 payments and support monthly close activities. Administer CaptivateIQ, including participant management, quota uploads, territories, crediting rules, rate tables, and plan configuration. Maintain comprehensive compensation documentation, plan logic, calculation methodologies, policies, and audit procedures.
**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 compensation costs. Support annual compensation planning, quota setting, territory planning, and compensation rollouts. Conduct market benchmarking and analyze industry trends to ensure programs remain competitive and effective.
**Analytics & Insights**: 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 and organizational structure. Partner with Revenue Leadership, Finance, and RevOps to provide recommendations that improve performance.
**Go-to-Market Support**: Serve as the primary point of contact for compensation questions from sales managers and individual contributors. Investigate and resolve commission disputes professionally and accurately. 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.
**Systems & Process Improvement**: Continuously identify opportunities to automate manual processes and improve data quality. Partner cross-functionally to enhance integrations between Salesforce, commission platforms, HRIS, payroll, and ERP systems. Leverage AI and automation tools to improve reporting and streamline workflows. Lead cross-functional projects that improve scalability, governance, and operational efficiency.
Ideal candidates have 3–6+ years of experience in Sales Compensation, Revenue Operations, Sales Operations, Finance, or Strategic Operations. Experience administering variable compensation plans in high-growth SaaS or technology companies is essential. Strong understanding of sales compensation principles, quota methodology, incentive design, and GTM operating models required. Hands-on experience with compensation platforms such as CaptivateIQ, Xactly, Everstage, Forma.ai, or Spiff is necessary. Advanced Excel and Google Sheets skills, including complex financial modeling and scenario analysis, are required.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
