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 Strategic and Mid-Market Sales Enablement Manager to join our Revenue Enablement team. This role reports to the Senior Manager, Sales Enablement and is the dedicated enabler for our Strategic and Mid-Market segment across new business and customer sales.
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, Marketing, Product Marketing, and Revenue Operations 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 segment enabler who understands that Strategic and Mid-Market selling lives between velocity and complexity. Deals run longer, involve more stakeholders, and reward consultative selling, so you build enablement that helps reps think on their feet while still moving deals forward efficiently. You do not wait to be told what to build. You study the calls, the pipeline, and the win and loss patterns, and you bring recommendations. You own outcomes for your segment, not just the delivery of sessions.
What you’ll work on
Own enablement for the Strategic and Mid-Market segment across new business and customer sales, covering both dedicated reps and their managers
Own measurable rep outcomes for the segment, including 90-day conversion rate, multi-product attach, and time to ramp
Build playbooks, discovery and multi-threading frameworks, objection handling, and value-based positioning for longer, more consultative cycles
Run a consistent Gong review rhythm on Strategic and Mid-Market calls to surface coaching themes, objection patterns, and content gaps
Design and maintain role-play and certification content grounded in real Strategic and Mid-Market conversations
Coach front-line managers on reinforcing trained behaviors so enablement lands in the field
Tailor product and multi-product enablement to the Strategic and Mid-Market buyer, including vertical and use-case depth
Use generative AI tools to accelerate content creation, role-play design, and iteration
Deliver a regular segment health readout covering what is working, what is not, and the top unmet needs
Partner with Sales Onboarding, Product Marketing, and Revenue Operations to keep proof points and playbooks current
Other duties as required
What you may have
5+ years of experience in sales enablement, mid-market or strategic sales, or a related learning and development role
Experience designing and delivering training for consultative, multi‑stakeholder sales teams
Familiarity with mid-market and strategic sales motions and the metrics that drive them
Knowledge of instructional design principles and adult learning theory
Strong facilitation and presentation skills across all levels of the organization
Comfort with tools such as Gong, Letter AIand Salesforce
Ability to analyze engagement and performance data to drive program improvements
Strong project management skills across multiple concurrent workstreams
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
Experience in legal tech or a comparable regulated industry
Relevant sales or enablement certifications
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
Versatile 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
The expected salary range for this role is $130,600 to $195,800 USD. Initial placement within the range is informed by geographic region, experience, and skillset, with room to progress as impact and tenure grow. Final offer amounts will vary based on candidate profile.
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 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.
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📌 Sales Enablement Manager, Strategic & Mid-Market (Ontario)
🏢 Clio
📍 Ontario