Supervisor, Microsoft Technology Specialists (Sales Specialist)

Softchoice; Toronto; On-site; CAD 85,000 - 100,000; Full time

Job summary

A leading IT solutions provider in Toronto is seeking a Supervisor for Microsoft Technology Specialists. This role requires strong leadership, customer relationship skills, and a solid understanding of Microsoft technologies. You'll coach a team, manage strategic customers, and collaborate with Microsoft resources to drive success. Ideal candidates will have 3+ years in Microsoft technology sales and excellent communication skills. The position offers a collaborative environment and competitive benefits.

Benefits

Competitive benefits

Flexible work environment

Career development opportunities

Qualifications

• 3+ years in Microsoft technology sales, licensing, or cloud solutions.
• Strong understanding of Microsoft programs (EA, CSP, MCA).
• Excellent communication and relationship building skills.
• Demonstrated ability to coach or lead others.

Responsibilities

• Guide and develop a subset of the Microsoft Technology Specialists team.
• Oversee execution across assigned territories.
• Personally manage a select book of strategic customers.
• Build strong relationships with Microsoft resources and account executives.

Skills

Coaching

Cloud solutions

Customer relationship building

Problem-solving

Microsoft programs knowledge

Education

3+ years in Microsoft technology sales

Bilingual (English/French)

Job description

Supervisor, Microsoft Technology Specialists (Sales Specialist)

Company: Softchoice

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 at work. That 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 recurring operational issues and recommend process improvements.

Sales & Customer Success Enablement

• 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.

Qualifications

• 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.

Additional Requirements

• Occasional travel for customer meetings, team collaboration, or Microsoft field alignment (U.S. & Canada).
• Bilingual (English/French) is an asset.

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.

Not sure if you qualify? Think about applying anyway:

We understand that not everyone brings 100% of the skills and experience for the role.

At Softchoice, we offer opportunities to a diverse group including those with a variety of workplace experiences and backgrounds. Whether you are new to corporate tech, returning to work after a gap in employment, or looking to transition and take the next step in your career, we are excited to learn more about you and encourage you to apply.

Why You’ll Love Working Here:

• The People: You’ll thrive in our collaborative environment, surrounded by incredible colleagues who foster support and innovation, driving our collective success.
• High-Performing Culture: At Softchoice, we are dedicated to achieving our goals and committed to success for our customers and each other.
• Flexibility: Plan your workdays in a way that suits you best.
• Award-Winning Workplace: Proudly recognized as a Great Place to Work for 20 consecutive years.
• Inclusive Culture: We are committed to an inclusive culture where every team member can be their authentic self.
• Competitive Benefits: Benefit from competitive perks that start on day one.

Inclusion & Equal opportunity employment:

We are an equal opportunity employer committed to diversity, inclusion & belonging. People seeking employment at Softchoice are considered without regard to any protected category including but not limited to, race, color, religion, national origin, age, sex, marital status, ancestry, disability, veteran status, gender identity, or sexual orientation.

Require accommodation? We are ready to help:

We are proud to provide interview & employment accommodation during the recruitment and hiring process. If you require any accommodation to apply or interview for a position, please reach out directly to [e-mail] . We are committed to working with you to best meet your needs.

Our commitment to your experience:

We are committed to the safety of all applicants and team members. With that in mind, we have implemented digital interviewing for everyone. We understand that you may need to interview with distractions around you (such as children or furry friends) and we will be doing the same.

Before you start with us, we will conduct a criminal record check, verify your education, and check your references.

When you join Softchoice, we will onboard you remotely. Don’t worry. It's quick, simple and you’ll be connected with your new team in no time.