Why you’ll love Softchoice:
We are a software-focused IT solutions and services provider that equips organizations to be agile and innovative, and for their people to be engaged, connected, and creative t means moving them to the cloud, helping them build the workplace of tomorrow, and enabling them to make smarter decisions about their technology. By doing these things we help them create success for their customers and their people.
We stand proudly for our people and support their success through career development and advancement. We are recognized and respected for our culture of inclusion and belonging, continuously striving to do what’s good for our people and communities.
About the Role
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.
Key Responsibilities
Team Coaching & Development
• 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.
Territory Support & Execution
• 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.
Customer Ownership
• 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.
Microsoft Alignment
• 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.
Operational Excellence
• 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…
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