Director, GTM Planning & Compensation

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. 

We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.

Revenue Operations is a strategic growth engine at Clio, accountable for optimizing how we acquire, expand, and retain revenue globally. We partner with Sales, Channel, Marketing, Customer Success, Finance, Legal, and Customer Support to design scalable GTM systems, align incentives to company strategy, and enable predictable, durable growth. The Revenue Operations team provides executive level insights, drives cross-functional decision making, and continuously improves GTM effectiveness through data, systems, and process excellence across North America, EMEA, and APAC.

We are seeking a Director of GTM Planning and Compensation to own and evolve Clio’s global GTM planning, territory design, and incentive compensation functions as a core lever of growth, performance, and behavior change. This role is available to candidates in Vancouver, Calgary, or Toronto, or remotely across Canada (excluding Québec) and the US.

This role is responsible for translating company and GTM strategy into capacity plans, territories, quotas, and incentive design that drives the right outcomes across Sales, Channel, and Customer Success. You will operate as a strategic advisor to GTM and Finance leadership, balancing competitiveness, simplicity, scalability, and financial discipline.

You will lead capacity planning, territory design and maintenance, and incentive compensation planning, governance, and administration globally, oversee compensation systems and analytics, and build a high-performing sales planning function that scales with  Clio’s rapid expansion. Your work will directly influence revenue predictability, seller behavior, retention, and long-term growth.

GTM Planning, Capacity & Quotas

• Leading GTM capacity planning and quota-setting, translating growth targets into coverage, headcount, and productivity plans across Sales and CS.
• Developing and evolving quota-setting methodologies, ensuring targets are grounded in market opportunity, historical performance, and productivity expectations.
• Partnering with Finance and GTM leadership to model capacity needs, ramp assumptions, productivity, and hiring requirements for annual and long-range planning, including scenario models that show the tradeoffs between headcount, coverage, quotas, productivity, compensation, and revenue before decisions are made.
• Establishing planning frameworks and analytics to monitor capacity, quota attainment, and productivity and inform in-year adjustments.
• Owning quota exceptions, relief policies, and disputes, balancing consistency with practical business judgment.

Territory Design & Maintenance

• Leading territory design and account segmentation, aligning selling resources with company strategy.
• Translating revenue targets into coverage models and account assignments, and identifying where the organization is over- or under-covered and what needs to change.
• Owning ongoing territory maintenance, including account assignments and in-year territory changes.

Compensation Strategy & Plan Design

• Owning and evolving Clio's global GTM compensation and rewards strategy spanning SMB and Enterprise segments, partnering with Sales, Channel, and CS leadership to ensure alignment with company objectives, GTM motions, and growth stages.
• Leading the design, modeling, and optimization of Sales and CS compensation plans, pay mix, quotas, accelerators, SPIFFs, and performance levers that drive desired behaviors, improve productivity, and support multi-year growth.
• Partnering with Finance and Sales/CS Ops to model plan effectiveness, risk, and ROI, leading quarterly and annual compensation effectiveness reviews (attainment distribution, cost of sale, capacity utilization), and ensuring plans support revenue predictability, margin targets, and financial planning.
• Developing and delivering clear, compelling compensation education and enablement programs for leaders, managers, and individual contributors, translating complex compensation concepts into simple, actionable narratives that build trust across GTM teams.

Compensation Administration & Systems

• Ensuring accurate, timely, and compliant compensation processing in partnership with Payroll, Finance, HR, Legal, and RevOps.
• Establishing and maintaining compensation governance, principles, and decision frameworks to ensure consistency, fairness, and scalability.
• Owning compensation communications, including plan documentation, guidelines, timelines, and appeals processes.
• Leading the refinement, governance, and continuous improvement of Clio's compensation and commission system (Forma.ai), driving automation, self-service, and operational excellence across regions.
• Championing automation, self-service, and AI capabilities across planning and compensation to improve accuracy, scalability, and stakeholder experience.

Leadership & Team Development

• Leading, coaching, and developing high-performing GTM planning and compensation teams, fostering accountability, strategic thinking, and continuous improvement.
• Building scalable processes and operating rhythms, including the cross-functional planning calendar with Finance, HR, and GTM leadership, that enable the team to move from transactional execution to strategic impact.
• Supporting change management for new plans, territories, tools, and policies across regions.
• Serving as a role model for cross-functional partnership, ownership, and results-driven leadership.

• 8+ years of experience in SaaS or technology, with direct ownership of capacity planning, territory, quota, and compensation design.
• Demonstrated ability to operate as a strategic advisor to senior GTM and Finance leaders.
• Excellent executive-level communication skills, both written and verbal.
• Experience leading and developing teams, with a focus on coaching and accountability.
• High integrity, sound judgment, and comfort handling sensitive information.
• Ability to thrive in ambiguity, make high-quality decisions with incomplete data, and drive outcomes in a fast-paced environment.
• Action oriented, ownership driven mindset with a strong bias toward impact and results.
• Proven ability to develop presentations with strong visual storytelling.
• Advanced Excel skills.
• Experience in translating measurements into recommendations, and connecting multiple data sources and building dashboards in data visualization tools (CRMA, Looker, Tableau, Google Sheets).
• Knowledge of statistical modeling techniques.
• Fluency in Salesforce data and at least one planning or ICM platform.

What you will find here:

Compensation is one of the main components of Clio’s Total Rewards Program. 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.
Some highlights of our Total Rewards program include: 

• 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

• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years

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Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility 

Our team shows up as their authentic selves, and are united by our mission. 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 believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.

Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.

Learn more about our culture at clio.com/careers

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. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions.

Disclaimer: We only communicate with candidates through official @clio.com email addresses.