Account Director (Individual Contributor) – Microsoft-Focused IT Services | Toronto

Job Description

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.

What You’ll Be Doing

• 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

What Makes This Opportunity Unique

• 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 <1% globally
• Ability to deliver end-to-end solutions (strategy → modernization → 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

Territory & Deal Profile

• 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

Compensation & Benefits

• 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

What’s Challenging About This Role

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