Microsoft Specialty Sales Executive

Softchoice • Toronto, ON

63d • $90,000 - $120,000

About The Position

Are you ready to be at the frontline of the most critical technology vendor for the majority of organizations?  Microsoft holds a critical position for many organizations across key solutions such as AI, Data, Security, Cloud, Collaboration, and Productivity, shaping the future of how organizations harness cutting-edge technology and creating competitive advantages.  As a pivotal member of our team, you won’t just be selling solutions—you’ll be empowering our customers to unlock the full potential of their Microsoft investments by helping create value across the Microsoft technology stack. 

At Softchoice, your influence will reach far beyond licensing and contracts. You’ll have the unique opportunity to architect and deliver solutions that become the backbone of our customers’ success, transforming how they enable their people to do more effective and efficient work at every corner of their technology landscape. Through our world class approach that leads customers on a journey by leveraging technical and licensing expertise, alongside deep alliances with Microsoft and their complimentary partner ecosystem, you’ll help organizations move from vision to execution. 

As a Customer Solution Architect - Microsoft Workplace, you will be the trusted advisor who brings clarity to complex challenges, guiding senior executives to align on a transformative Microsoft solutions roadmap. You’ll be instrumental in shaping business cases that deliver reduced operational costs, improved security posture, improved productivity and collaboration—while mapping out the tangible roadmap milestones that drive executive buy-in and long-term adoption. 

In this role, you’ll quarterback a high-performing team of account executives, solution architects, licensing and technical experts, orchestrating seamless collaboration to deliver solutions tailored precisely to each customer’s unique needs. You’ll facilitate boardroom-level discussions, influence strategic decision-making, and see your recommendations come to life in ways that redefine what’s possible for your clients. 

If you’re passionate about making a lasting impact, eager to champion Microsoft solution adoption, and thrive on building relationships that fuel innovation—this is your chance to be the catalyst for real change, helping organizations across industries shape their futures with confidence and clarity.

Requirements

• The ideal candidate will bring 7+ years of demonstrated success in solutions sales, specifically focused on Microsoft platforms. This experience should include a proven track record in selling multi-vendor integrated solutions and professional services, as well as supporting enterprise / upper commercial RFPs, proposals, and executive presentations.
• Proficiency with M365 (Security and Collaboration), Copilot (AI Business Solutions) and Public Cloud (Azure Solutions)
• Proficiency with Teams, Intune/Autopilot, Entra ID, Defender, and Zero Trust concepts
• Proficiency with Microsoft Cloud Solution Provider (CSP) program and associated services to drive adoption across Modern Work, Security, and Cloud technologies
• The candidate should possess the ability to translate executive-level objectives into a well-structured roadmap and adoption plan. They must be able to present a clear narrative connecting multiple solution areas to desired business outcomes, and have the ability to communicate business value to executive stakeholders.
• Proven capability in leading virtual pursuit teams and coordinating partner co-selling and funding efforts is essential.
• The candidate should be familiar with Microsoft platforms and how to advocate for Professional and Managed Services that help customers deploy, adopt, and manage those platforms.
• Willingness and ability to travel frequently within a designated Sales District, up to 50% of the time.

Nice To Haves

• Relevant certifications will be rewarded.

Responsibilities

• Generate demand and build sales pipeline for Microsoft-specific solutions in a defined territory including ownership of the Revenue and Gross Profit attainment.
• Own the executive sales cycle from discovery to close: map business problems to offers, orchestrate virtual teams (pre‑sales architects, delivery, partners), shape proposals/SOWs, and negotiate to signature.
• Lead with value/ROI: you will build business cases, success metrics, and adoption plans for measurable impact.
• Take a services-led approach to help clients architect and design architecture as it relates to collaboration, productivity, security, and AI solution platforms
• Help customers define best practices and key processes and systems to provide guidance on Microsoft best practices and efficiencies
• Facilitate C-level conversations to enhance understanding of Microsoft and bring alignment at customers to specific Microsoft initiatives
• Partner co‑sell & funding: align with Microsoft to unlock workshops, customer incentives, and POC funding motions that accelerate deals.
• Pipeline discipline: maintain accurate Salesforce hygiene and weekly cadence on funnel adds and sufficiency; leverage Sales Ops dashboards.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed