Customer Success Training Program Jobs in Toronto, ON

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 seeking a Program Manager, Digital Customer Success to own the execution and evolution of Clio's digital customer success strategy. Working closely with customer success leadership, operations, and cross-functional partners, you will design and run retention and adoption programs that scale across a high-volume SMB base through personalized digital touchpoints, automation, and 1:many resources. Success in this role is measured by churn reduction, NRR impact, and the measurable customer value you create through increased product adoption.

The Scaled Customer Success Program sits within Clio's Customer Success organization and is responsible for the scaled programs, digital journeys, and automated interventions that help a large and diverse customer base thrive across Clio's growing product suite. We work at the intersection of customer success, marketing, product, and data science, creating proactive experiences that drive retention, expansion, and customer value at scale.

• Program Execution & Development: Manage day-to-day execution of digital customer success programs including journey configuration, trigger logic, segmentation, and reporting.

• Process Improvement: Document and maintain playbooks and program governance frameworks. Identify and implement AI-assisted workflows that automate and streamline operations, freeing the team for higher-impact work.

• Program Enablement: Build and maintain internal resources that keep the broader customer success organization informed on program priorities, upcoming launches, and performance.

• Data & Program Insights: Own reporting of program performance including engagement metrics, churn indicators, adoption trends, and NRR impact. Gather and synthesize feedback from AMs and CSMs to inform program iteration.

• Content & 1:Many Programs: Partner with Marketing and Customer Education to align content across email, in-app messaging, and educational resources. Orchestrate 1:many programs that drive engagement and product adoption at scale.

You're organized and operate with a high level of ownership and agency. You bring structure to complex problems and can turn direction into action. You're genuinely excited about AI as a practical tool you reach for every day to eliminate manual work, generate insights faster, and build smarter programs.

• Break complex initiatives into clear, manageable plans

• Work comfortably with data and translate findings into next steps

• Look for every opportunity to automate and accelerate work using AI

• Communicate clearly and manage cross-functional relationships with ease

• Adapt when priorities shift without losing momentum

• 2-4 years of experience in program management, customer success, revenue operations, or a scaled/digital CS model

• Hands-on experience with customer success or marketing automation platforms such as ChurnZero, Gainsight, Totango, or similar

• Demonstrated ability to manage multiple concurrent workstreams with strong attention to detail and consistent follow-through

• Experience building and maintaining playbooks, process documentation, or operational SOPs

• Comfort working with data: pulling reports, building dashboards, and summarizing metrics for stakeholders

• Strong written and verbal communication skills with a bias toward proactive, clear communication

• A genuine interest in AI tools and how they can improve workflows and scale programs more effectively

• Familiarity with the legal technology sector

• Background in customer lifecycle marketing, email automation, or in-app engagement

• Exposure to customer health scoring frameworks or adoption metrics

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, London, New York City and Sydney) to be in office min. twice per week.

• Flexible time off policy, with an encouraged 20 days off per year.

• $2000 annual counseling benefit

• RRSP matching and RESP contribution

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

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

Our team shows up as their authentic selves, and are united by our mission. We are dedicated todiversity, 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 atclio.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.