Senior Sales Specialist - Windows and Device Sales

Microsoft•Toronto, ON

1d•CA$142,800 - CA$214,900

About The Position

With a vision to build and sell Microsoft AI‑powered platforms, cloud services, and devices through a broad partner ecosystem, the Windows and Device Sales (WDS) organization brings together sales, technical expertise, and partners to help customers achieve meaningful business outcomes with Microsoft technology. WDS plays a critical role in shaping and delivering the endpoint platform that powers modern, secure, and AI‑enabled work. WDS works across Microsoft’s commercial ecosystem, including OEMs, silicon partners, distributors, resellers, and services partners, to drive Windows platform adoption, strengthen technology security and help customers realize long‑term value from their device and endpoint investments. This role contributes to a multi‑billion‑dollar business and plays a direct role in securing and expanding Windows as a trusted enterprise endpoint platform. You will work with customers to modernize their environments, adopt AI‑driven workflows, and build confidence in Windows as the foundation for future innovation. As a Windows and Device Sales Specialist, you will strengthen and expand Windows within Microsoft’s largest and most strategic customers. You will help them define and modernize their endpoint strategy in an era shaped by AI, security threats, and rapid platform competition. You will operate as a trusted advisor to senior IT and business leaders, anchoring engagement with the CIO while expanding influence across CTO, CISO, and AI transformation leaders to ensure Windows remains the trusted platform for secure, AI‑driven work. In this role, you will lead high‑impact, time‑bound customer engagements where Windows platform decisions are at risk or strategically critical. You will articulate the value of Windows across security, resiliency, management, and AI workloads; orchestrate partners and internal teams to deliver proof and outcomes; and translate successful customer engagements into repeatable best practices that can be scaled across industries and partner ecosystems. This opportunity will allow you to deepen executive‑level consultative skills, expand your technical and platform expertise across the Windows ecosystem, and play a visible role in protecting and expanding Microsoft’s commercial footprint in priority accounts. Microsoft’s mission is to empower every person and every organization on the planet to achieve more. As employees we come together with a growth mindset, innovate to empower others, and collaborate to realize our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.

Requirements

Bachelor's Degree in Computer Science, Information Technology, Business Administration, Information Security, or related field AND 6+ years experience in technology-related sales or account management OR equivalent experience.
6+ years solution or services sales experience.
Demonstrated experience in leading technical and executive‑level customer conversations, translating complex platform concepts into clear, outcome‑oriented guidance for CIO, CTO, CISO, and AI transformation leaders.
Background in technical sales, solutions architecture, GBB or platform Specialist roles, where credibility across both business outcomes and technical depth was required.
Experience with Microsoft Security and compliance technologies, including Microsoft Defender, Entra, Purview, identity and access management, and Zero Trust principles, with the ability to translate technical capabilities into business value and risk reduction outcomes.
Experience with Windows platform expertise, including Windows Pro and Windows 11 Enterprise, with the ability to articulate differentiated value across security, manageability, performance, and AI for enterprise and commercial customers.
Experience advising customers on Windows 11 lifecycle strategy, including hardware refresh planning, security posture improvements, and operational readiness.
Demonstrated experience of modern endpoint management and workplace transformation strategies with expertise in Microsoft Intune, Configuration Manager and cloud-native management. Able to advise senior leaders on device management modernization, security, operational efficiency and AI readiness, guiding customers through strategic platform decisions and transformation roadmaps.
Understanding of AI-ready Windows devices, including Copilot+ PCs, NPUs and specialized AI silicon. Able to translate platform and hardware innovation into measurable business outcomes, productivity gains and competitive advantage for customers evaluating next-generation endpoint strategies.

Nice To Haves

Master's Degree in Business Administration (i.e., MBA), Information Technology, Information Security, or related field AND 8+ years experience in technology-related sales or account management OR Bachelor's Degree in Computer Science, Information Technology, Business Administration, Information Security, or related field AND 12+ years experience in technology-related sales or account management OR equivalent experience.

Responsibilities

Lead Windows endpoint strategy with senior executives: Leverage your technical expertise to lead strategic Windows discussions with CIOs, CTOs, CISOs and AI leaders, translating technology capabilities into business value.
Defend and extend Windows in competitive environments, deepen insights on why customers adopt alternative platforms, articulate fact based & differentiated platform value to protect the Windows socket.
Modernize endpoint management and identity architectures, helping customers decouple from legacy environments, improve total cost of ownership, and unlock AI‑driven workflows at scale.
Lead high‑impact customer engagements across discovery, envisioning, proof, and value realization, with clear entry criteria, success measures, and exit plans.
Deliver impactful wins that demonstrate real Windows AI value, converting customer outcomes into evidence such as case studies, reference architectures, and repeatable industry scenarios.
Orchestrate across internal teams and partners, working closely with account teams, engineering, and OEM/channel partners to ensure clarity of roles, clear hand-offs, escalation process, and accelerated outcomes.
Provide structured feedback and insights from customer engagements to inform product, go‑to‑market, and partner strategy, identifying patterns that can scale across similar customers.
Embody our Culture & Values