Director, Revenue Enablement

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.

We are currently seeking a Director of Revenue Enablement to join our Revenue Operations team. This role is open to candidates across Canada and the U.S.

Revenue Operations drives growth by supporting our revenue-generating and revenue-retaining teams. We are working closely with Channel, Sales, Marketing, Finance, Channel, Customer Enablement and Customer Support to provide insights and recommendations, improve the efficiency of the GTM motions, and enable GTM teams to be innovative and self-sufficient.

Reporting to the VP of Revenue Operations, the Director of Revenue Enablement is responsible for building a modern, high velocity, AI-forward enablement function that supports Clio’s global growth across Sales, Sales Development, Partners, and Customer Success. This leader treats enablement as an operational discipline, not a training function. They diagnose where the GTM system is breaking, build the infrastructure to fix it, and deliver programs that directly improve productivity, velocity, and conversion.

The right leader is fast, analytical, and deeply scrappy with real range. They operate as an organizational leader who can mobilize cross functional teams to drive impact, and as a doer who jumps in to build the model, the content, and the systems themselves. They design field support models that scale and turn complex ideas into clear, actionable guidance that Sales and CS can execute immediately. They can build playbooks from zero and translate ideas from marketing in a succinct and efficient manner. They have a point of view on what great looks like in a multi product environment and know how to operationalize it.

They will influence executive level decisions, partner tightly with Product Marketing, Sales Leadership, Customer Success, and RevOps, and pioneer AI-driven enablement programs that scale globally.

• Design the full enablement operating model for a multi product GTM including field support structure, content strategy, AI-powered workflows, and continuous learning.

• Lead a high performing team that ships fast, measures impact, and acts as a strategic partner to frontline managers.

• Build a data driven review process that evaluates program effectiveness, identifies gaps, and continuously raises the bar on productivity and conversion.

• Create onboarding and continuous development programs that materially shorten ramp and lift performance across every segment.

• Continuously diagnose and evolve the sales process by defining the skills, knowledge, tools, and process changes needed to increase velocity and win rates, leveraging AI, voice analytics, and behavioral insights to surface win-loss patterns and inform real-time coaching and optimization.

• Partner closely with Product Marketing to build original, high quality sales playbooks and training programs that connect positioning, messaging, discovery, objections, and pitches into winning habits across front line teams.

• Stand up a real field support model that provides reps with timely deal support, live coaching, and targeted resources to remove friction.

• In partnership with Customer Marketing and CS Ops, build customer growth and retention playbooks that improve GRR and NRR across segments.

• In partnership with Corporate Events, own the full SKO strategy, design and execution, and refinement and delivery of a high quality program including content, executive presentations, run of show, and all readiness materials that move the GTM org forward.

• Own the enablement content strategy using LetterAI and lead all AI-driven coaching through Hyperbound, providing hands on support and a clear plan for maximizing both tools to ensure the field is fully trained, confident, and ready to execute.

• Serve as a go-to subject matter expert by maintaining deep expertise in Clio’s products, buyers, and customers, while staying current on industry trends, best practices, and emerging technologies in revenue enablement.

• Bachelor's degree in business or a related field. MBA is a plus!

• 10+ years of experience in a senior leadership role leading enablement teams at a SaaS company

• Experience at a company of $400M+ ARR (preferably an SMB SaaS company) 

• Experience driving SKO strategy, design and execution 

• Proven track record of driving operational excellence and outcomes that are tied to specific enablement programs 

• Track record of hiring, developing, and retaining top talent to build high-performing teams

• Strong ability to build future vision and activate direct reports 

• Problem solver who is comfortable operating with ambiguity, autonomy, providing radical feedback and taking ownership

• Analytical problem solver who can build, analyze and discuss quantitative business metrics with finance and RevOps

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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*Our salary bands are designed to reflect the range of skills and experience needed for the position and to allow room for growth at Clio. For experienced individuals, we typically hire at or around the midpoint of the band. The top portion of the salary band is reserved for employees who demonstrate sustained high performance and impact at Clio. Those who are new to the role may join below the midpoint and develop their skills over time. The final offer amount for this role will be dependent on geographical region, applicable experience, and skillset of the candidate.

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.