Revenue Operations 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.

Job Description

We're looking for a Revenue Operations 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 Captivate IQ, 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 Rev Ops 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 administrative effort.
• Lead cross-functional projects that improve scalability, governance, and operational efficiency.
• What We Are Looking For
• 3–6+ years of experience (Analyst) or 5–8+ years (Senior Analyst) in Sales Compensation, Revenue Operations, Sales Operations, Finance, or Strategic Operations
• Experience administering variable compensation plans in a high-growth Saa S or technology company
• Strong understanding of sales compensation principles, quota methodology, incentive design, and GTM operating models
• Hands-on experience with a compensation platform such as Captivate IQ, Xactly, Everstage, Forma. ai, Spiff, or similar
• Advanced Excel and/or Google Sheets skills, including complex financial modeling and scenario analysis
• Strong working knowledge of Salesforce CRM
• Experience partnering with Payroll, Finance, and Accounting on commission processing
• Excellent analytical and problem-solving skills with exceptional attention to detail
• Outstanding written and verbal communication skills with the ability to explain complex compensation concepts simply
• Ability to manage multiple priorities in a fast-paced, ambiguous environment
• Bachelor's degree in Finance, Accounting, Economics, Business, Mathematics, Statistics, or a related quantitative field
• Nice to Have
• Experience supporting multiple GTM functions (Sales, SDR, Customer Success, Partnerships, Solutions Engineering)
• Experience with SQL, Sigma, Tableau, Looker, or Power BI
• Familiarity with ARR-based Saa S metrics and forecasting
• Experience implementing or administering compensation software
• Experience using AI tools to improve reporting, automation, and operational efficiency
• What Success Looks Like

Within your first year you will

• Own accurate, on-time commission processing with strong audit controls and minimal manual intervention.
• Become a trusted advisor to Sales, Finance, and Revenue Leadership on compensation-related questions.
• Improve the scalability and automation of our compensation operations.
• Deliver meaningful analysis that influences compensation design, quota planning, and territory strategy.
• Help build compensation programs that are transparent, motivating, and aligned to company growth.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels.

Tailscale's compensation package includes base salary, equity, and comprehensive benefits.

The salary range displayed on each job posting represents the target range for a new hire's base salary.

Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)

_Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications._ We encourage you to help us break that statistic!

What We Offer

An inclusive, flexible environment where you can be your authentic self.

We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company.

And that flexibility in how and when you work empowers our team to integrate work and life.

A competitive total compensation package.

This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

Comprehensive group benefits with no waiting period.

Take advantage of coverage for health, vision, dental, and more for you and your family!

Remote first company —most of our teams work fully remotely.

Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit We Work (or other similar spaces near you).

Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.

Employer-funded retirement contributions.

Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

Connect with other Tailscalars IRL.

Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.

We support intentional in-person connection through team travel and distributed collaboration.

Support for your personal and professional development.

Grow your career thoughtfully with 1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

Paid time off and a healthy work-life integration.

Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!

A build-your-own home office setup.

You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and 500 USD to customize your workstation to make it your own.

Paid parental leave program .

We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

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