Customer Success Learning Specialist

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.

Summary

We are currently seeking a Customer Success Enablement Specialist to join our Revenue Enablement team in Toronto, Vancouver, or Calgary.

What Your Team Does

The Revenue Enablement team at Clio equips our sales and customer success organizations with the knowledge, skills, tools, and processes they need to drive revenue growth and deliver exceptional client experiences. We design and deliver onboarding and ongoing programs, run a center of excellence operating model, and partner closely with Sales, Customer Success, Marketing, and Product Marketing to turn product launches into field-ready execution. We are a team that runs on curiosity, data, and a genuine commitment to helping people do their best work.

Who you are

You are a customer success enablement professional who builds programs that actually change what CSMs do in front of customers. You understand the full customer lifecycle, from onboarding through adoption, expansion, and retention, and you know how to translate a product story into the conversations that grow accounts. You bring strong facilitation skills and a data-informed mindset, and you do not wait to be told what to build. You look at the calls, the usage data, and the outcomes, and you come to the table with recommendations.

What you’ll work on

• Build and deliver customer success enablement programs across the lifecycle, covering onboarding, product launches, adoption, expansion, and retention motions
• Translate launch playbooks into CS-specific talk tracks for upsell, cross-sell, and multi-product attach
• Partner with CS Onboarding to sequence the living segment playbook into a 30-60-90 day ramp for new CSMs
• Design and maintain certification content for CS, including role-play scenarios grounded in real expansion and retention conversations
• Run a weekly Gong review rhythm on CS calls to surface coaching themes, objection patterns, and content gaps
• Coach CSM managers on reinforcing trained behaviors so enablement lands in the field, not just in the session
• Deliver a monthly CS enablement health report covering what is working, what is not, and the top unmet needs
• Track program impact against customer success outcomes such as expansion ARR, multi-product attach, retention, and ramp time
• Use generative AI tools to accelerate content creation, role-play design, and iteration
• Partner with Marketing, Product Marketing, and Legal experts to keep CS proof points current and credible
• Other duties as required

What you may have

• 2+ years of experience in customer success, CS enablement, or a related learning and development role
• Experience designing and delivering training for customer-facing teams
• Familiarity with customer success motions such as onboarding, adoption, expansion, and retention
• Knowledge of instructional design principles and adult learning theory
• Strong facilitation and presentation skills with the ability to communicate clearly across all levels of the organization
• Comfort with tools such as Gong, LetterAI, and Salesforce
• Ability to analyze engagement and performance data to drive program improvements
• Strong project management skills with the ability to move multiple workstreams forward simultaneously

Serious bonus points if you have

• Experience in a SaaS or technology company
• Experience enabling expansion, cross-sell, or multi-product attach motions
• Proficiency with generative AI tools (Claude, ChatGPT, or similar) for content development and ideation
• Relevant customer success or enablement certifications
• Experience partnering with Marketing and Product Marketing on content and proof points

This role is a backfill for an existing position.

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

The expected salary range* for this role is $78,200 to $92,000 to $105,800 CAD. There are a separate set of salary bands for other regions based on local currency.

• 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.