Strategic & Mid-Market Sales Enablement Lead

Clio; Toronto; Hybrid; CAD 181,000 - 272,000; Full time

Benefits offered by this job

Hybrid work environment

20 days off per year

Health benefits

Dental and vision insurance

401k matching

Clioversary program

Job summary

Clio, the global leader in legal AI technology, is 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 acts as the dedicated enabler for our Strategic and Mid-Market segment across new business and customer sales.

You’ll design onboarding and ongoing programs, build playbooks, run Gong review rhythms, and partner with Sales, Marketing, Product Marketing and Revenue Operations to keep

Qualifications

• 5+ years of experience in sales enablement or related learning and development
• 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

Responsibilities

• Own enablement for the Strategic and Mid-Market segment across new business and customer sales
• Own measurable rep outcomes including 90-day conversion rate and time to ramp
• Build playbooks and multi-threading frameworks for longer sales cycles
• Run Gong review rhythm to surface coaching themes and content gaps
• Design and maintain role-play and certification content
• Coach managers to reinforce trained behaviors
• Tailor product enablement to Strategic and Mid-Market buyers
• Use generative AI tools to accelerate content creation
• Deliver segment health readouts and partner with Sales Onboarding and Revenue Operations

Skills

Sales enablement

Mid-market sales

Instructional design

Adult learning

Facilitation

Analytics

Project management

Training design

Tools

Gong

Letter AI

Salesforce

Job description

Clio, the global leader in legal AI technology, is 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 acts as the dedicated enabler for our Strategic and Mid-Market segment across new business and customer sales.

You’ll design onboarding and ongoing programs, build playbooks, run Gong review rhythms, and partner with Sales, Marketing, Product Marketing and Revenue Operations to keep