Account Director; Individual Contributor – Microsoft-Focused IT Services

Join a well-established ~$100M IT services and managed services provider that’s scaling its Toronto-based sales team while driving broader North American growth. With deep Microsoft expertise and a strong delivery engine, the company is now investing in formal sales structure, leadership, and go-to-market strategy.

This is a high-impact opportunity for a consultative, outcome-driven seller who thrives in complex environments and wants visibility into real growth.

• Owning and driving net-new logo acquisition across mid-market to small enterprise accounts ($50M–$2B revenue).
• Leading consultative, multi-threaded sales cycles across:
  • Cloud (Azure)
  • Managed Services
  • Data & AI
  • Dynamics 365 (ERP/CRM)
  • Application Modernization
  • Security
• Diagnosing complex business and technical challenges and mapping solutions across the Microsoft ecosystem.
• Partnering closely with Microsoft on co-sell motions, target accounts, and pipeline development.
• Collaborating with technical SMEs and delivery leaders to build proposals and close sophisticated, outcome-based deals.

• High-visibility role within a growing Toronto team tied to broader North American expansion.
• ~80% Microsoft-based revenue with partner distinctions placing the organization among the top less than 1% globally.
• Ability to deliver end-to-end solutions (strategy to modernization to managed services), competing with firms like Deloitte and Accenture.
• Strong delivery infrastructure—sellers are supported by experienced technical teams.
• Proven track record of winning and expanding complex engagements, including displacing large global SIs.

• Based in Toronto with North American coverage (primarily U.S.
  
  -focused accounts).
• Deal range:
  • Entry: ~$1K MRR
  • Core engagements: $20K–$60K MRR
  • Larger projects: up to ~$1M+
• Sales cycles range from transactional to enterprise-level, depending on scope and urgency.

• Base Salary: $120K–$150K CAD
• OTE: ~$240K–$300K CAD (uncapped, ~50/50 split)
• Extended health benefits (medical, dental, vision)
• HSA-style options
• RRSP matching
• Strong employer contribution toward benefits

Navigating complex, technical buying environments while selling across a broad Microsoft ecosystem. Top performers are able to:

• Diagnose interconnected systems (often starting with ERP)
• Sell business outcomes vs. point solutions
• Lead stakeholders through ambiguity and long-cycle decisions

• Proven success selling IT services and/or professional services
• Strong exposure to Microsoft ecosystem (Azure, Dynamics 365, ERP-adjacent solutions)
• Experience with in a mid-sized MSP or IT services firm strongly preferred
• Highly consultative, business-outcome focused approach
• Comfortable owning deals end-to-end and partnering with technical teams
• Bachelor’s degree preferred