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

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 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.
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 RoleNavigating 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
Qualifications
Proven success selling IT services and/or professional services
Strong exposure to Microsoft ecosystem (Azure, Dynamics 365, ERP-adjacent solutions)
Experience within 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
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