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Director, Sales Enablement
Category: Sales – SALARY
Brand: Corporate Compass Group
Employment Status: Salary
Starting Rate: $105000.00 CAD
Location: 1 Prologis Boulevard, Mississauga, ON
Posting Date: 2026-05-29T15:00:05.913Z
The Director, Sales Enablement is a senior strategic leadership role responsible for designing, executing, and continuously optimizing the sales enablement strategy that drives sales productivity, revenue growth, and customer impact. This role partners closely with Sales, Marketing, Revenue Operations (COE), Program Management, Onboarding, and Account Management to ensure go-to-market teams are equipped with the tools, frameworks, analytics, and insights required to perform at the highest level. Operating at both a strategic and executional level, the Director ensures alignment between business objectives and frontline sales behaviors, while establishing scalable enablement programs that improve win rates, shorten sales cycles, and accelerate time-to-value post-close.
Now, if you were to come on board as our Director, Sales Enablement we’d ask you to do the following for us:
- Sales Enablement Strategy & Leadership
- Define, lead, and evolve the enterprise-wide sales enablement strategy aligned to revenue and growth objectives
- Partner with senior leadership to shape go-to-market priorities, sales motions, and performance frameworks
- Establish enablement governance, standards, and best practices across the revenue lifecycle
- Strategic Deal Enablement
- Lead enablement support for complex, high-value sales opportunities
- Partner with Sales and COE to ensure deal structures, pricing, and proformas are financially sound and competitively positioned
- Translate deal strategy into executive-level narratives, materials, and frameworks that elevate win rates
- Cross-Functional Alignment & Influence
- Act as a central connector across Sales, Marketing, Revenue Operations, Finance/COE, and Operations
- Ensure consistent messaging, analytics, sales pitches, and coordinated execution across functions
- Influence without direct authority to drive alignment, adoption, and execution quality
- Post-Sale Mobilization & Handoff
- Own the transition from deal close to onboarding and account management
- Develop standardized handoff processes, playbooks, and accountability models
- Reduce risk, accelerate onboarding, and improve customer outcomes post-close
- Performance Measurement & Insights
- Define and track enablement KPIs (e.g., win rates, sales cycle duration, market basket performance)
- Leverage data and insights to continuously improve sales effectiveness
- Translate analytics into actionable guidance for Sales leadership
- Team Leadership & Change Management
- Lead adoption of new tools, processes, and enablement initiatives across the sales organization
- Build, coach, and scale the sales enablement function over time
- Foster a culture of continuous improvement, accountability, and execution excellence
- Executive Communication & Advisory
- Provide regular insights and recommendations to executive leadership
- Advise on sales effectiveness, deal quality, and revenue optimization opportunities
- Serve as a senior advisor on enablement strategy and commercial performance
Think you have what it takes to be our Director, Sales Enablement? We’re committed to hiring the best talent for the role. Here’s how we’ll know you’ll be successful in the role:
- Bachelor’s degree in Business, Commerce, Marketing, or a related field (required)
- MBA or equivalent advanced degree (preferred)
- 10+ years of progressive experience in Sales, Sales Enablement, Revenue Operations, or related commercial roles
- Demonstrated experience supporting or influencing complex, high-value deal cycles
- Strong commercial and financial acumen, including pricing, proformas, and deal economics
- Proven ability to influence and align senior stakeholders across multiple functions
- Experience building scalable enablement programs, tools, and frameworks
What’s in it for you?
- Join an award-winning culture. We have been recognized for being a Great Place to Work, in addition to being selected as a FORTUNE Global 500 Company, Best Workplaces Retail & Hospitality, and FORTUNE World’s Most Admired Companies.
- The opportunities with us are endless. As the world’s largest food and support services company, we offer an extensive range of learning and career opportunities for all our associates.
- Health & Safety. The health and safety of our associates, clients and guests has always been our top priority. We have the right processes in place to ensure our teams have the support they need to stay safe, while helping to keep our guests safe.
- Health Benefits. For our eligible associates, we offer comprehensive health, vision, and dental care coverage.
- A Focus on Mental Health and Wellness. Our Mental Health and Well-Being initiative was created to share credible resources with our associates and the communities we serve on a variety of topics, including mental, physical, spiritual, and financial wellbeing. We also have an Employment Assistance Program which provides our associates with access to 24/7 support, resources, and information.
- We are as diverse as our guests. We believe diverse and inclusive environments support innovation and collaboration, and benefit our associates, clients, and customers. We are committed to Listen, Learn, and Act and our Diversity Inclusion Action Councils (DIAC) are associate led groups that seek to foster inclusion through cultural awareness, engagement and appreciation of diversity. We are Stronger, Together!
Compass Group Canada is committed to nurturing a diverse workforce representative of the communities within which we operate. We encourage and are pleased to consider all qualified candidates, without regard to race, colour, citizenship, religion, sex, marital / family status, sexual orientation, gender identity, aboriginal status, age, disability or persons who may require an accommodation, to apply.
For accommodation requests during the hiring process, please contact ukg.recruitment@compass-canada.com for further information.
This post is also available in:
Français
This post is also available in:
Français

