Director of Client (Customer) Success

The Director of Client Success is responsible for ensuring client satisfaction, retention, and long-term value across our client base, primarily law firms. This is an Executive-level role that builds strong, trusted relationships with key stakeholders, understands client business goals, and ensures clients achieve meaningful outcomes from our legal software platform.

Leading a team of five Client Success Managers, the Director will establish best practices and processes for client engagement, adoption, risk management, renewals, and expansion. They will define and execute the client success strategy, while fostering a culture of accountability, client advocacy, and continuous improvement. Working cross-functionally with Sales, Implementations, Support, Product, and Renewals, this role serves as the voice of the client internally. The ideal candidate thrives in a fast-paced environment rapidly evolving product features, and who can execute tasks quickly and efficiently while working both independently and as part of a team.

About LEAP
LEAP is the leading provider of Legal Practice Productivity Solutions in the world and is part of ATI – one of the largest international LegalTech companies. For more than 30 years, our curiosity and commitment to continual improvement have kept us reimagining productivity tools for lawyers and their staff to support our guiding purpose, which is to ‘Help lawyers who help people.’ The market-leading software we develop, and support is used by more than 100,000 lawyers and their staff in small and medium-sized law firms.

Working alongside our international team of passionate high achievers, you’ll join a fast-growing technology business where things seldom stay the same for long. With more than 1000 smart, caring and ambitious ‘LEAPsters’ working together across Australia, Canada, the United States, the United Kingdom, the Republic of Ireland, Poland and New Zealand, you’ll be in good company here.

KEY RESPONSIBILITIES AND ACCOUNTABILITIES

• Manage, lead, and mentor the Client Success team
• Oversee processes for minimizing churn, managing client risk, and driving product value, ensuring retention revenue growth and satisfaction
• Develop and maintain deep expertise in LEAP, including legal content, AI capabilities, and integrated partner solutions
• Understand the LEAP product ethos, value proposition, and position in the marketplace, confidently communicating this to clients and external stakeholders
• Work with varying departments to implement, test, and measure initiatives and product updates aimed at improving adoption, client experience, and retention
• Educate and empower clients on LEAP’s innovative features through client webinars, newsletters, and best practice initiatives, driving early adoption, efficiency, and productivity

• Identify at-risk clients using health indicators, usage data, and engagement signals, and lead proactive intervention strategies to mitigate churn
• Serve as the senior escalation lead for high-risk client situations, guiding de-escalation, coordinating cross-functional efforts, and protecting client relationships and retention
• Provide structured feedback to LEAP teams on client needs, trends, and pain points, and lead cross-departmental collaboration to resolve issues
• Measure, analyze, and report on client product adoption KPIs, engagement metrics, and success outcomes
• Maintain regular client engagement processes throughout the lifecycle, ensuring clients are maximizing LEAP’s capabilities and implementing success strategies where adoption is low
• Recruit, onboard, and develop new members for the Client Success team

REQUIRED QUALIFICATIONS

• 5+ years of experience in a similar client-facing role with a technology company
• Experienced seasoned manager with outstanding leadership, mentoring, and recruiting skills
• Ability to leverage data to inform and support critical decisions
• Familiarity with dealing with client conflict in a positive manner
• Exceptional organizational skills and self-discipline
• Positive and professional attitude
• Ability to leverage cross-functional business and technical resources to provide timely issue resolution
• An aptitude for quick learning
• An in-depth knowledge of the latest versions of Word, Excel and Outlook
• Superb communication skills, both written and verbal
• A passion for technology

Preferred (but not required):

• An understanding of Legal Accounting rules and bookkeeping
• Familiarity with Gainsight and Tableau
• Knowledge of QuickBooks and/or Xero
• A thorough understanding of varying law firms' culture and expectations

BENEFITS

What you'll get

Why work at LEAP?

There are endless opportunities within our business to progress and grow your career and full training is provided so an aptitude and hunger to learn is essential. We offer:

• Competitive compensation with a base salary and a bonus structure. The base salary band for this role ranges from: $100,000 CAD - $140,000 CAD annually. Salary will be based on level of experience.
• Excellent group insurance benefits
• RRSP with employer matching
• Generous Paid Time Off (PTO), including starting at 4 weeks’ vacation, sick days, floater/personal days and volunteer days
• Hybrid working model at our beautiful and modern downtown Toronto office as well as work from home days
• Collaborative and inclusive work environment filled with learning and support

At LEAP,

We care about what we do and the people we work with

We continually improve to be the best

We NEVER EVER GIVE UP!

At LEAP we are committed to fostering an inclusive and accessible environment. We are dedicated to building a workforce that reflects the diversity of the community in which we live, including those with disabilities. LEAP is committed to providing accommodations in all parts of the hiring process. If you require accommodation, we will work with you to meet your needs