Technical Sales Specialist (Microsoft 365)

TL;DR

Technical Sales Specialist (Microsoft 365): Driving revenue and scaling technical sales capabilities for the ShareGate product line with an accent on sales enablement and AI-driven workflows. Focus on building reusable technical assets, delivering high-impact demos, and bridging the gap between field patterns and product roadmap.

Location: Remote (Must be based in Canada)

Salary: $90,000 – $110,000 CAD (plus commissions, OTE ~$100k–$120k)

Company

hirify.global is a Montreal-based tech company specializing in HR platforms and Microsoft 365 migration and governance solutions.

What you will do

• Lead technical sales onboarding and ongoing enablement to empower reps to handle technical conversations independently.
• Drive deals to close as a technical co-closer, reinforcing value and navigating technical gaps with product vision.
• Develop standard-setting demos and reusable technical assets to shorten deal cycles.
• Translate field patterns into structured feedback for Product Managers to shape the product roadmap.
• Create AI-powered workflows and playbooks to scale technical leverage across the sales team.
• Support expansion conversations for existing customers to increase product attach rates.

Requirements

• Experience in a customer-facing technical sales role within a B2B SaaS environment.
• Familiarity with the Microsoft 365 platform (governance or migration experience is a plus).
• Must be based in Canada.
• Proven track record of influencing deals to close with high business acumen.
• Fluency in building AI workflows and a builder mindset for scaling knowledge.
• Strong communication skills for audiences ranging from IT admins to CIOs.

Nice to have

• Bilingual proficiency in French and English.

Culture & Benefits

• Environment that values experimentation, rapid learning, and ownership.
• Culture of trust and mutual support in both success and failure.
• Flexible work environment adapted to daily life and individual needs.
• Inclusive work culture focused on healthy professional relationships.

Hiring process

• Phone Screen.
• Virtual Interview via Microsoft Teams.
• Work Sample.
• Job Offer.