Head of Sales Enablement

  • Category: Operations Executive Jobs
  • Location: Toronto, Ontario
  • Job Type: Full Time / Part Time
  • Salary: Estimated: $ 18K to 24K
  • Published on: 2025/09/16

We are working with a high-growth tech company that is leading in their space! Their business management software is helping their customers maximize profits. They are profitable and growing, with over 3000 business owners on their platform.

Report into CRO

Develop and Implement Sales Training Programs: Design, create, and deliver a comprehensive range of sales training programs aimed at reducing sales ramp time and enhancing performance in achieving sales quotas and productivity.

Establish Metrics for Program Impact: Set up metrics to evaluate the effectiveness of sales enablement programs.

Collaborate on Sales Onboarding Programs: Work with Sales, Marketing, Product, and Revenue Operations teams to create a world-class sales onboarding and continuous enablement program, focusing on product knowledge, sales methodology, and tool adoption.

Work closely with the entire GTM leadership team to define sales enablement and onboarding strategy.

Equip Sales Teams for Success: Ensure sales teams have the necessary content and skills to position the value of offerings across various buyer personas effectively and successfully execute deal cycles.

Identify Skill Gaps and Develop Content: Build strong relationships with sales and product leadership to identify needs and skill gaps, and develop enablement content and deliverables to address them.

Design Partner Onboarding Tracks: Collaborate with marketing and partnership teams to design, develop, and deliver partner onboarding tracks.

Build strong internal relationships to align teams, and successfully drive projects and revenue goals.

REQUIREMENTS

10+ years of experience leading successful and global sales enablement programs.

Experience working in a high-velocity SaaS environment

Strong executive presence, including excellent written and verbal communication skills and stakeholder management abilities.

Deep understanding and ability to coach on sales competencies, methodologies, and frameworks.

A problem solver who is comfortable operating with ambiguity and autonomy, taking ownership of tasks and projects.

Naturally proactive, with a bias towards action while developing forward-looking roadmaps.

Director-level experience.

A leadership philosophy focused on people and culture development.

Exceptional strategic thinker with a hands-on approach to execution, capable of translating visionary concepts into actionable plans that deliver measurable results.

Collaborative mindset with a proven ability to build and nurture relationships at all levels of the organization, fostering a culture of innovation, accountability, and excellence.

Entrepreneurial spirit with a passion for driving innovation and challenging the status quo.

Located in Toronto but hybrid/flexible WFH arrangements

BENEFITS

Opportunity to lead and influence the marketing function

Competitive compensation including equity

4-day work week

Hybrid remote with 2X a week in office located in Markham

Joining a company that puts people and culture first


Company Name: The Leadership Agency

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