Softchoice · 4 days ago
Supervisor, Microsoft Technology Specialists (Sales Specialist)
North Dakota, United States
Full-time
Hybrid
Mid, Senior Level
3+ years expSoftchoice is a software-focused IT solutions and services provider that helps organizations innovate and engage their people. The Microsoft Technology Sales Specialist Supervisor plays a key leadership role, guiding a team of specialists and managing strategic customer relationships to enhance Microsoft solution execution and customer experience.
Cloud ComputingCollaborationInformation Technology
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
Qualification
Required
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
Fluency in English is required for this position, as the candidate will have to collaborate daily with unilingual English-speaking colleagues and clients outside Quebec
Preferred
Bilingual (English/French) is an asset
Benefits
Competitive Benefits
Company
Softchoice
Softchoice provides technology services and solutions for people to be engaged, connected, and creative at work.
1001-5000 employees
H1B Sponsorship
Softchoice has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
2022 (2)
2021 (1)
2020 (1)
Funding
Current Stage
Public CompanyTotal Funding
unknownKey Investors
Birch Hill Equity Partners
2024-12-31Acquired
2021-05-27IPO
2013-01-01Private Equity
Leadership Team
Andrew Caprara
President & CEO
Jeff Reis
SVP - IT & Workplace
Recent News
2025-12-30
2025-12-18
Company data provided by crunchbase