Supervisor, Microsoft Technology Specialists (Sales Specialist)

Softchoice

About The Position

The Microsoft Technology Sales Specialist (MTS) Supervisor plays a key leadership role within our Microsoft organization, supporting the Manager of Microsoft Technology Specialists by guiding a small team of MTSs while maintaining ownership of a select set of strategic customers. This role helps ensure consistency in execution across Azure, M365, Copilot, and licensing motions, while enabling MTSs to deliver exceptional customer experience, deepen technical conversations, and advance Microsoft opportunities. The Supervisor is responsible for coaching, daily support, and performance oversight for MTSs who may be earlier in their career, regionally aligned, or supporting specific customer segments. This role is essential to scaling customer coverage, strengthening our Azure and Microsoft solution execution, and establishing a talent pipeline for future senior MTS and leadership roles.

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).
Strong organizational skills with the ability to balance coaching, customer ownership, and internal alignment.
Excellent communication, relationship building, and problem-solving skills.
Ability to influence cross-functionally and collaborate across teams (AEs, MTAs, Inside MS Specialists, SA, CSM).
Track record of strong customer outcomes, revenue impact, and Microsoft alignment.

Nice To Haves

Bilingual (English/French) is an asset.

Responsibilities

Support the Microsoft Sales Manager in leading and developing a subset of the MTS team.
Provide daily coaching on customer conversations, Azure/M365 opportunity development, value positioning, and technical engagement best practices.
Conduct regular 1:1s, call coaching, and opportunity reviews to strengthen performance and consistency.
Identify skills gaps and partner with leadership to implement enablement, certification plans, and readiness programs.
Foster a positive, collaborative team culture that values learning, accountability, and customer obsession.
Oversee consistency in execution across assigned regions or customer segments, ensuring alignment with sales plans and Microsoft priorities.
Support MTSs in developing customer roadmaps, renewal strategies, and pipeline creation across Azure, M365, Security, and Copilot.
Monitor workload distribution, opportunity alignment, and execution gaps within the supervisor's sub-team.
Act as the first escalation point for day-to-day licensing, technical, or customer challenges.
Personally manage a select book of strategic or high-impact customers.
Lead customer discovery, Azure or M365 solution positioning, and renewal/value conversations.
Support key deals where deeper experience or executive presence is needed.
Model best practices in strategic customer engagement for junior MTSs.
Build strong working relationships with Microsoft field resources (AEs, specialists, STUs, PDMs) within the Supervisor's territory or segment.
Foster collaborative working relationships with Softchoice sales management and Account Executives to drive Microsoft growth across assigned territories and customers.
Ensure MTSs are aligned to Microsoft's priorities, funding programs, and co-sell motions.
Participate in Microsoft pipeline calls, planning meetings, and partner strategy discussions as an extension of the Microsoft Sales Manager
Share field insights and feedback to leadership to refine strategy and improve alignment.
Ensure consistent use of tools (SFDC), documentation, and processes across the team.
Review pipeline hygiene, opportunity alignment, licensing recommendations, and contract accuracy for the team's accounts.
Support execution of renewals, Azure consumption planning, and customer lifecycle milestones.
Collaborate with MTAs, Inside Microsoft Specialists, and Professional Services to ensure a seamless customer experience.
Surface recurring operational issues and recommend process improvements.
Guide MTSs in identifying upsell and cross-sell opportunities across Azure, M365 Security, Copilot, and modernization services.
Ensure licensing recommendations connect to customer adoption and long-term value realization.
Assist in coordinating workshops, assessments, funding programs, and technical resources.
Partner with Customer Success and Solution Architecture to reinforce consistent customer lifecycle execution.
Support the development of MTSs to advance into senior MTS or Azure Specialist roles.
Recommend promotions, development plans, and succession paths for high-potential talent.
Contribute to a scalable leadership structure that supports future growth of the Microsoft business.