Director, Sales Enablement Jobs in Mississauga, ON
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Mississauga, ON
Director, Sales Enablement
Top Benefits
About the role
The salary range for this position is $105,000 to $125,000. Final compensation will be determined based on relevant skills, experience, qualifications, and internal equity. In addition to base salary, eligible employees may be entitled to other elements of total compensation, which may include group benefits, employer RRSP contributions, and discretionary bonus or incentive programs, where applicable to the role. We are committed to offering competitive compensation and comply with all applicable pay transparency legislation. Further details regarding our total rewards program will be shared by the Talent Acquisition team during the hiring process. Canadian work experience is not a requirement for this role. Please note that artificial intelligence–based tools may be used at certain stages of the recruitment and applicant screening process.
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 Enablementwe’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
Not the right fit? Search for Director, Sales Enablement jobs in Mississauga, ON
About Compass Group
Compass Group PLC is a world leading food and support services company, which serves meals to millions of people in c.35 countries and employs and engages more than 550,000 people globally. The Company specialises in providing food and a range of support services across the core sectors of Business & Industry, Healthcare & Senior Living, Education, Sports & Leisure and Defence, Offshore & Remote, with an established brand portfolio.