Microsoft Solutions Sales Specialist (AI)

TL;DR

Microsoft Solutions Sales Specialist (AI): Driving demand and orchestrating the sales cycle for Microsoft-specific solutions with an accent on AI, Cloud, and Security. Focus on architecting business cases for C-level executives and leading virtual pursuit teams to deliver transformative technology roadmaps.

Location: Toronto, ON, CA (Hybrid)

Salary: $105,000–$120,000 annually + 40% Target Incentives

Company

A software-focused IT solutions and services provider that enables organizations to modernize their workplace, migrate to the cloud, and make smarter technology decisions.

What you will do

• Generate demand and build a sales pipeline for Microsoft-specific solutions within a defined territory.
• Manage the full executive sales cycle from discovery to close, including shaping proposals and SOWs.
• Develop business cases, success metrics, and ROI-led adoption plans for measurable impact.
• Architect solution designs for collaboration, productivity, security, and AI platforms.
• Facilitate C-level conversations to align customer business goals with Microsoft initiatives.
• Partner with Microsoft to activate co-sell motions and unlock POC funding and incentives.

Requirements

• 7+ years of demonstrated success in solutions sales specifically focused on Microsoft platforms.
• Proficiency with M365 (Security and Collaboration), Copilot (AI Business Solutions), and Azure.
• Expertise in Teams, Intune/Autopilot, Entra ID, Defender, and Zero Trust concepts.
• Strong knowledge of the Microsoft Cloud Solution Provider (CSP) program.
• Ability to translate high-level executive objectives into structured roadmaps and adoption plans.
• Willingness and ability to travel frequently within the sales district, up to 50% of the time.

Culture & Benefits

• Comprehensive medical and dental care, including an Employee & Family Assistance Program.
• RRSP/DPSP retirement savings plan with company matching.
• Generous paid time off, including vacation, sick leave, parental leave, and volunteer days.
• Flexible work arrangements to help you plan your workdays effectively.
• Inclusive, award-winning workplace culture recognized for 20 consecutive years.