Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

Senior Sales Compensation Analyst In this role, you'll own a meaningful share of Clio's monthly commission execution while also partnering with the Director of Revenue Compensation on plan design, policy, and the strategic questions that shape how we incentivize our GTM organization. We work closely with Sales, Marketing, Finance, Channel, Customer Enablement, and Customer Support to provide insights and recommendations, improve efficiency of GTM motions, and enable GTM teams to be innovative and self-sufficient.

Sales

Compensation sits at the heart of that — turning strategy into the plans, quotas, and incentives that move the business, and ensuring every rep is paid accurately and on time. Who you areYou take pride in getting commission execution right — accurate payouts, clean audits, well-documented processes — and you're equally comfortable stepping back to ask bigger questions about plan design, quota setting, and what the data says about our GTM motion. You may come from a sales compensation background, a strategic RevOps or finance role, or a management consulting firm — what matters is that you bring both operational discipline and strategic curiosity.

Partner with the Director of Revenue Compensation on the design, modeling, and refinement of sales compensation plans, SPIFFs, and incentive structures — translating GTM strategy into plan mechanics that drive the right rep behavior.



Investigate and resolve commission inquiries from sales reps and managers in a timely, qualified manner, building trust with the GTM organization. Diagnose patterns across attainment, payout, and pipeline data to surface insights and recommend changes to plan design, quota setting, and territory construction.

Prepare and validate sales data used by payroll for commission and incentive calculations, meeting weekly deadlines. Identify and lead process and system improvements (commission tooling, documentation, controls, policy) to scale the comp function as Clio grows. Maintain comprehensive documentation of plan logic, calculation methodology, audit procedures, and policy decisions. 4+ years of progressive experience in sales compensation, revenue operations, business operations, strategic finance, or management consulting.

Working knowledge of Salesforce (CRM).

Advanced

Excel and Google Sheets modeling skills, including the ability to build scenario models and plan simulations from scratch. Solid commercial and financial acumen — able to model plan economics, weigh trade-offs (cost of comp, motivational pull, fairness), and connect plan design to GTM strategy and company OKRs.



Excellent communication and stakeholder management skills, with the confidence to present recommendations to senior Sales, Finance, and RevOps leaders.

A bachelor's degree in Economics, Finance, Accounting, Business, Statistics, or a related quantitative field. Decision quality — keeps projects and priorities tied to Clio's OKRs and the team's main initiatives. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.

Competitive, equitable salary with top-tier health benefits, dental, and vision insurance Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin and Sydney) to be in office minimum twice per week. Flexible time off policy, with an encouraged 20 days off per year. EAP benefits for you and household members, including counseling and online resources 401k matching and Child Education Savings Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility We are dedicated to diversity, equity and inclusion.

We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency.

📌 Senior Sales Compensation Analyst (Winnipeg)
🏢 Clio
📍 Winnipeg