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Sales Enablement Manager, Strategic & Mid-Market

Job in Calgary, Alberta, D3J, Canada
Listing for: Clio
Full Time position
Listed on 2026-09-12
Job specializations:
  • Sales
    Sales & Marketing, Business Development
Salary/Wage Range or Industry Benchmark: 130600 CAD Yearly CAD 130600.00 YEAR
Job Description & How to Apply Below
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 work streams

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,…
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