Sales Enablement Manager, Strategic & Mid-Market in Winnipeg

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. 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.

Who you are:

• You are a segment enabler who understands that Strategic and Mid-Market selling lives between velocity and complexity.
• You build enablement that helps reps think on their feet while still moving deals forward efficiently.
• 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 AI and 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:

• 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.

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.