Sales Enablement Manager, Strategic & Mid-Market

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.

Flexible 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

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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 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.