Supervisor, Microsoft Technology Specialists (Sales Specialist)

TL;DR

Supervisor, Microsoft Technology Specialists (Sales Specialist): Guiding a team of Microsoft Technology Specialists while overseeing a portfolio of strategic customers with an accent on Azure, M365, Copilot, and licensing. Focus on coaching MTSs, deepening technical conversations, and advancing Microsoft opportunities.

Location: Toronto, ON, CA or Montreal, Quebec, CA. Occasional travel for customer meetings, team collaboration, or Microsoft field alignment (U.S. & Canada).

Company

hirify.global is a software-focused IT solutions and services provider.

What you will do

• Support the Microsoft Sales Manager in leading and developing a subset of the MTS team.
• Provide coaching on customer conversations, Azure/M365 opportunity development, value positioning, and technical engagement best practices.
• Personally manage a select book of strategic or high-impact customers.
• Build strong working relationships with Microsoft field resources (AEs, specialists, STUs, PDMs) within the Supervisor’s territory or segment.
• Ensure consistent use of tools (SFDC), documentation, and processes across the team.
• Guide MTSs in identifying upsell and cross-sell opportunities across Azure, M365 Security, Copilot, and modernization services.

Requirements

• 3+ years in Microsoft technology sales, licensing, cloud solutions, or a similar customer-facing Microsoft role.
• Strong understanding of Microsoft programs (EA, CSP, MCA), Azure fundamentals, and M365 solutions.
• Demonstrated ability to coach, mentor, or lead others (formal leadership experience preferred but not required).
• Excellent communication, relationship building, and problem-solving skills.
• Ability to influence cross-functionally and collaborate across teams (AEs, MTAs, Inside MS Specialists, SA, CSM).
• Fluency in English is required.

Nice to have

• Bilingual (English/French) is an asset.

Culture & Benefits

• Collaborative environment with supportive colleagues.
• Dedicated to achieving goals and committed to customer success.
• Flexibility in planning workdays.
• Recognized as a Great Place to Work.
• Committed to an inclusive culture.
• Competitive benefits starting on day one.