Manager, Microsoft Operational Excellence in Winnipeg

At Softchoice, a World Wide Technology (WWT) company, we work together to make a new world happen. As an IT solutions provider serving U.S. commercial and SMB organizations, as well as the entire Canadian market, we help organizations turn ambition into real‑world outcomes through the delivery of secure cloud, AI, software and digital workplace solutions that enable agility, innovation and growth.

The Manager, Operational Excellence is responsible for leading the operational execution of Microsoft's licensing business and ensuring customer transactions are completed accurately, efficiently, and in alignment with Microsoft program requirements and internal business standards. This role provides people leadership and operational oversight across the full licensing transaction lifecycle, including quoting, contract creation and maintenance, ordering, amendments, renewals, and other related licensing activities.

A key focus of the role is establishing and maintaining strong operational controls. This includes partnering with Microsoft and internal compliance teams, monitoring adherence to program and contractual requirements, maintaining audit readiness, and ensuring compliance requirements are consistently applied throughout each transaction.

The successful candidate will bring strong operational judgment, licensing knowledge, and a continuous‑improvement mindset. They will strengthen the business through disciplined execution, clear accountability, effective controls, and thoughtful improvements to processes and tools.

What You'll Do:

• People Leadership and Team Development: Lead, coach, develop, and retain a high‑performing Microsoft Operations team. Establish clear objectives, expectations, and accountabilities aligned with department and business priorities. Conduct regular one‑on‑one meetings, performance discussions, development planning, and objective monitoring.
• Operational Leadership and Execution: Lead the day‑to‑day execution of Microsoft licensing operations across quoting, contracting, ordering, amendments, renewals, and ongoing agreement maintenance. Ensure transactions are completed accurately, on time, and in accordance with Microsoft requirements, customer commitments, and internal standards.
• Microsoft Program and Transaction Compliance: Partner with Microsoft to understand changes to licensing programs, operational requirements, transaction rules, and partner obligations. Translate Microsoft requirements into clear internal procedures, controls, training, and operational practices.
• Operational Excellence and Continuous Improvement: Identify opportunities to simplify processes, eliminate unnecessary steps, improve quality, and reduce operational risk. Lead practical improvements to workflows, documentation, controls, reporting, and supporting tools.
• Cross-Functional Partnership and Stakeholder Management: Build effective working relationships with Microsoft and internal stakeholders across Sales, Customer Success, Finance, Legal, Compliance, IT, Enablement, and other business areas.
• Governance, Risk, and Business Management: Identify operational, compliance, financial, and customer risks within the processes managed by Microsoft Licensing Operations. Establish mitigation plans, monitor corrective actions, and elevate material risks appropriately.

What You Will Bring to the Table:

• At least three years of progressive experience in licensing operations, customer operations, sales operations, or a related technology environment.
• Demonstrated people‑leadership experience, including coaching, performance management, talent development, and workload planning.
• Strong experience managing complex, high‑volume, transaction‑based operations.
• Practical knowledge of software licensing, contract processing, quoting, ordering, renewals, and agreement maintenance.
• Experience interpreting external program or partner requirements and translating them into internal processes and controls.
• Strong analytical and problem‑solving skills, with the ability to identify root causes and drive issues through resolution.
• Proven ability to work cross‑functionally with Sales, Finance, Legal, Compliance, IT, Customer Success, and external partners.
• Strong written and verbal communication skills, including the ability to communicate operational risks and requirements to senior stakeholders.
• A strong customer focus balanced with appropriate attention to compliance, accuracy, financial risk, and contractual obligations.
• Post‑secondary education in business, operations, technology, or a related discipline, or equivalent relevant experience.

Compensation: A reasonable estimate of the current base pay range for this position in Canada is $95,000 to $110,000, annually + 12% as target incentives. Actual salary will be based on a variety of factors, including location, experience, skill set, education, and related certification.

Benefits: Softchoice offers a comprehensive and competitive benefit plan to all full‑time employees, which includes medical and dental care, employee & family assistance program, RRSP/DPSP retirement savings plan with company matching, life and disability insurance, vacation and sick leave, holidays, parental leave, volunteer days, bereavement leave, and employee discount program.

We are 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.