Strategic & Mid‑Market Sales Enablement Lead

Clio; Calgary; Hybrid; CAD 183,000 - 275,000; Full time

Benefits offered by this job

Health benefits

Dental insurance

Vision insurance

Hybrid work environment

20 days off per year

401k matching

Job summary

Clio, the global leader in legal AI technology, seeks a Strategic and Mid-Market Sales Enablement Manager to empower the Revenue Enablement team across new business and customer sales. You will own segment outcomes, build playbooks, and ensure content stays aligned with evolving sales motions.

You will design role-plays, certifications, and multi-threading frameworks, while coaching managers to reinforce training in the field; use AI tools to accelerate content creation and delivery.

Qualifications

• 5+ years in sales enablement, mid-market or strategic sales, or related learning 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.

Responsibilities

• 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.

Skills

Sales enablement

Strategic selling

Mid-market selling

Instructional design

Facilitation

Gong

Salesforce

Data analysis

Tools

Gong

Salesforce

Letter AI

Job description

Clio, the global leader in legal AI technology, seeks a Strategic and Mid-Market Sales Enablement Manager to empower the Revenue Enablement team across new business and customer sales. You will own segment outcomes, build playbooks, and ensure content stays aligned with evolving sales motions.

You will design role-plays, certifications, and multi-threading frameworks, while coaching managers to reinforce training in the field; use AI tools to accelerate content creation and delivery.