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Director of Sales Enablement

GDI Integrated Facility Services - 4 Jobs
Mississauga, ON
Posted 2 days ago
Job Details:
Full-time
Management

Join the GDI Family!

One provider. One solution. All your facility maintenance services.

GDI provides unequalled capability and expertise in the facility services sector across Canada and the United States. Our broad knowledge and competencies in integrated facility services will contribute to the success of our business partners. With nearly a century of experience, our excellent service delivery distinguishes us from other facility services providers. Our team of over 30,000 individuals offer innovative cleaning techniques, best-in-class capabilities, and unrivaled experience.

The Senior Sales Enablement Leader - Pursuit Management at GDI will lead the end-to-end strategy, content, and execution for high-value, competitive pursuits. This individual will work closely with sales executives, operations leaders, estimations and marketing teams to drive excellence in RFP responses, proactive proposals, and strategic deal positioning.

This role is critical to increasing win rates, shortening sales cycles, and elevating GDI's market positioning during complex procurement events.

Key Duties:

Pursuit Management Leadership

  • Own and lead GDI's pursuit management framework for large and strategic opportunities (RFPs, RFIs, unsolicited proposals).
  • Facilitate pursuit kickoffs, strategy sessions, and win-theme development with cross-functional teams.
  • Serve as a deal coach for regional and national account sales teams, offering input on deal strategy, solutioning, and value proposition alignment.
  • Manage production timelines and final submissions, ensuring proposals are client-centric, on-brand, and compelling.

Sales Enablement & Content Strategy

  • Support and develop pursuit playbooks, reusable content libraries, and RFP response templates aligned with GDI's brand and service excellence.
  • Support sales onboarding and ongoing training for pursuit management best practices.
  • Collaborate with Marketing, Operations, and other key stakeholders to gather and tailor win themes, case studies, KPIs, and differentiators for target sectors.

Operational Efficiency & Analytics

  • Establish metrics to track pursuit outcomes, win/loss analysis, and feedback for continuous improvement.
  • Create a scalable, repeatable system for content updates and pursuit execution using tools like Microsoft D365, and SharePoint.
  • Partner with Operations, Legal, and Estimations for compliance and pricing strategy support.

Requirements:

Must-Have Qualifications

  • 5-10+ years of experience in sales enablement, strategic pursuit management, or proposal management within B2B services or similar industries.
  • Proven track record of managing successful RFPs and large deal pursuits (>$1M) in a service-driven environment.
  • Deep understanding of facilities services, outsourcing, or professional services procurement cycles.
  • Outstanding communication, editing, and executive storytelling skills.
  • Expertise in Microsoft Office Suite, Canvas, Adobe Acrobat, and collaboration tools; or proposal automation tools a plus.

Preferred Qualifications

  • Experience supporting field and enterprise sales in a matrixed organization.
  • Familiarity with SLAs, unionized labor requirements, and facilities compliance standards.
  • Strong grasp of commercial pricing strategies and contract structures.

Key Attributes for Success

  • Operates as a proactive internal consultant and partner to the sales field.
  • High attention to detail with the ability to juggle multiple pursuits and deadlines.
  • Strategic mindset with a roll-up-your-sleeves attitude.
  • Strong project management, people influencing, and deadline execution skills.
  • Passion for elevating the customer experience in every touchpoint of the sales cycle.

GDI Services Inc. is an equal opportunity employer.

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