Sr. Director - Microsoft Services

SHI International Corp.•Stratford, ON

3d•Hybrid

About The Position

The Senior Director, Microsoft Services is accountable for the success, growth, and strategic direction of SHI’s Microsoft Services practice, spanning Modern Work, Azure, Security, Data, and AI. This role leads the practice as a business, with ownership of service maturity, headcount planning, utilization, delivery quality, and measurable client outcomes. The Senior Director sets strategy, builds delivery and leadership capability across internal teams and partner ecosystems, and ensures services remain modern, scalable, well-governed, and aligned with evolving Microsoft platforms and enterprise customer needs.

Requirements

Executive-level communication skills with the ability to align stakeholders across sales, delivery, engineering, and partner teams.
Strategic leadership that sets clear direction, builds followership, and drives measurable business outcomes.
Strong judgment and analytical thinking when navigating ambiguity, competing priorities, and tradeoffs.
Credibility and influence as a trusted advisor to enterprise clients.
An innovation mindset that improves services and delivery models while maintaining governance, quality, and organizational readiness.
Strong business acumen, including operating a services practice with accountability for utilization, capacity, pipeline health, and profitability.
High standards for accountability, execution, and follow-through across complex, cross-functional initiatives.
Willingness to travel to SHI, partner, and customer events (approximately 25%).
Ability to scope, plan, and govern complex Microsoft services engagements across Modern Work, Azure, Data, and AI.
Experience partnering closely with internal sales/presales teams and Microsoft field organizations on strategic pursuits.
Ongoing commitment to maintaining technical and leadership currency through continuous learning and relevant certifications.

Nice To Haves

10+ years of leadership experience within a technology services organization, with a focus on Microsoft solutions.
Deep understanding of enterprise Microsoft platforms, such as Exchange Online, Microsoft Entra ID, SharePoint Online, Windows 365, and Azure infrastructure.
Proven track record of leading and scaling technical services teams and service offerings.
Experience delivering complex enterprise programs with strong delivery governance.
Exposure to data platforms and AI applications; familiarity with infrastructure as code is a plus.
Ability to clearly communicate complex technical concepts to executive and cross-functional audiences.

Responsibilities

Set and execute a clear strategic vision for the Microsoft Services practice, translating market trends and Microsoft platform signals into prioritized investments and repeatable offerings.
Establish and maintain delivery standards, governance models, and best practices to ensure consistent, scalable, and high-quality outcomes.
Drive continuous improvement across service delivery, quality, and operational readiness to improve customer satisfaction and overall practice health.
Lead the evolution of service offerings across Modern Work, Azure, Security, Data, and AI to ensure engagements are outcome-driven, well-governed, and aligned to enterprise needs.
Build, lead, and retain high-performing teams of engineers, architects, and delivery leaders, with clear career paths and expectations for delivery excellence.
Own skills development and leadership coaching to ensure teams can deliver modern Microsoft services reliably and at scale.
Ensure strong technical currency across Microsoft’s portfolio through a disciplined approach to training and relevant certifications.
Serve as an executive advisor to enterprise clients, connecting business priorities to Microsoft strategies that drive adoption, value realization, and sustained outcomes.
Provide executive oversight for complex programs, ensuring strong delivery governance, risk management, and accountability to scope, timelines, budgets, and quality standards.
Partner with sales and presales teams on strategic pursuits, shaping scope, delivery approach, and proposals that clearly articulate business outcomes.
Ensure a world-class customer experience through proactive communication, executive visibility, and consistent delivery excellence.
Maintain a platform-aware perspective across Microsoft’s enterprise portfolio to ensure services align with Microsoft roadmaps and customer demand.
Collaborate with Microsoft field and partner teams to drive joint solutions and enablement, strengthening SHI’s enterprise delivery capabilities.
Collaborate across Cloud, Data, AI, and Security teams to deliver integrated outcomes and avoid siloed delivery.
Ensure delivery teams are equipped with modern architectures, reference patterns, and readiness guidance to keep engagements secure, supportable, and repeatable.
Drive growth of professional services revenue by shaping offerings, supporting strategic pursuits, and expanding enterprise client relationships.
Own practice operations, including utilization, capacity planning, and pipeline health, to maximize performance and profitability.
Develop and maintain executive relationships with key clients and partners to drive trust, retention, and growth.
Ensure engagements are scoped responsibly, with clear assumptions, success criteria, and measurable outcomes.