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About the Role

Clio is seeking a Sr. Manager, Sales, Enterprise to lead and grow the Enterprise Account Executive team in Toronto. This role involves coaching, developing, and empowering AEs to sell legal technology solutions to prestigious law firms and corporate legal departments, shaping strategy, and elevating sales execution.

Responsibilities

• Lead, coach, and develop a team of Enterprise Account Executives to consistently exceed quota.
• Drive the strategy and execution of sales plays across top-tier named accounts, while refining repeatable sales motions and documenting best practices.
• Partner with your team on high-impact conversations with senior decision-makers, from managing partners to innovation leads to C-suite executives.
• Create a culture of excellence in enterprise selling, with mastery of value-based, consultative approaches.
• Collaborate cross-functionally with Legal Architects, product, R&D, marketing, and customer success to shape solutions and ensure a unified go-to-market approach.
• Hire, onboard, and scale a world-class team of Enterprise AEs.
• Own pipeline health, forecast accurately, and provide market insights to guide leadership decisions.
• Represent Clio at industry forums and client events, positioning both yourself and your team as thought leaders in legal AI.

Requirements

• Proven sales leader who thrives in complex, consultative enterprise environments.
• Experience navigating the legal market and commanding the room with senior partners, general counsel, and C-level executives.
• Track record of coaching enterprise sellers to success.
• Deep understanding of shaping and closing large, multi-stakeholder deals.
• Motivated by building high-performing teams and delivering outsized results.
• A history of exceeding targets as both an enterprise seller and a sales leader with experience building or scaling teams in high-growth environments.
• Demonstrated experience managing and coaching high-performing Enterprise Account Executives in B2B SaaS, ideally within legal tech or adjacent verticals.
• Proven ability to earn trust and build strong executive-level relationships within AmLaw 100 firms or Fortune 500 corporate legal departments.
• Deep expertise in complex, multi-threaded enterprise deals with long sales cycles and significant deal values.
• Strong leadership presence, with exceptional communication, coaching, and motivational skills.
• Comfort operating in a high-growth, rapidly evolving environment.
• Willingness to travel to support team members in the field, attend client meetings, and represent Clio at strategic events.
• Growth mindset when it comes to process improvement and new technologies, especially AI.

Skills

• Sales leadership
• Enterprise sales
• Coaching
• Team development
• Strategic planning
• Sales execution
• Consultative selling
• Value-based selling
• AI technology
• Legal technology
• B2B SaaS sales
• Executive relationship building
• Pipeline management
• Forecasting
• Communication
• Motivation

Location

• Toronto

Work Type

• Hybrid

Experience Level

• Sr. Manager
• Enterprise seller
• Sales leader

Salary/Compensations

• Expected salary range: $108,800 to $163,200 CAD
• Expected new hire commission range: $108,800 to $163,200 CAD
• Commissions are uncapped

Benefits

• Competitive, equitable salary
• Top-tier health benefits, dental, and vision insurance
• Flexible time off policy, with an encouraged 20 days off per year
• $2000 annual counseling benefit
• RRSP matching
• RESP contribution
• Clioversary recognition program

About the Company

• 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.
• Clio is a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations.
• Clio is on a mission to transform the legal experience for all.
• Clio is the global leader in legal AI, building the platform that powers the future of legal work.
• With the scale, data, and ambition to redefine how the legal industry operates, we are advancing a comprehensive strategy that spans the full lifecycle of legal work—from knowledge and insight to execution and outcomes.
• At the center of this vision is the Intelligent Legal Work Platform, the legal industry’s first System of Action.
• By combining Clio’s core product suite with Clio Work and AI-native capabilities, the platform turns information into insight and insight into action.
• As we expand into the enterprise, Clio for Enterprise extends this foundation to support the complexity, scale, and operational rigor of global organizations through solutions like Clio Operate and Vincent by Clio.
• Backed by industry-leading data and intelligence, Clio is building the infrastructure that enables legal teams to operate with greater speed, confidence, and impact.
• Clio’s leadership and momentum have been recognized globally.
• In 2022, we achieved Centaur status, a milestone reached by fewer than 200 private SaaS companies worldwide.
• We are a proud honoree of the Forbes Cloud 100 and Fortune’s Future 50, have been named Innovator of the Year, and are a Platinum Club member of Canada’s Best Managed Companies.
• We are consistently recognized as one of Canada’s Top 100 Employers and a Top Employer for Young People, with our international offices also earning placements on Great Place to Work’s Best Workplaces lists.
• Headquartered in Vancouver, Canada, Clio has grown to more than 2,000 employees across offices in Toronto, Calgary, Dublin, Manchester, Sydney, Barcelona, and Bogotá—bringing together diverse perspectives to solve one of the world’s most complex and impactful professional challenges.
• Join Clio and help define the future of legal work through AI.
• Learn more at clio.com/careers.

Equal Opportunity

• 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.