About ShareGate ShareGate is the leading Microsoft 365 migration and governance platform, trusted by over 100,000 IT pros for its unmatched simplicity. It offers the simplest, most reliable, and most affordable way to move business data to Microsoft 365. Whether migrating from Google Workspace, file shares, Exchange Online, SharePoint On-Premises, or tenant-to-tenant, ShareGate gets the job done, without surprises.

From cloud transformation to M A integration, it keeps things just damn simple. ShareGate also helps organizations stay in control once their data is migrated. Its powerful governance features let users assess environments, uncover issues, and apply fixes on the spot, so everything stays clean, secure, and optimized.

It lays the groundwork for safe Microsoft Copilot deployment within organizations. ShareGate is developed by Workleap Technologies, a Montréal‑based software company. Your role This isn't the Technical Sales Specialist role of five years ago.

We're not looking for someone who just shows up on every technical call. We're looking for a builder — someone who knows when to jump on a call because the deal demands it, and when to instead build the system, training, or asset that lets a rep handle that same call confidently next time. When you're in a deal, you're not just validating fit.

You're reinforcing value, navigating technical gaps with vision and roadmap, and helping close. Your impact: Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of technical conversations independently — without routing everything through TSS ; Eliminate the single point of failure on technical depth by taking real load off the existing TSS across pre-sales, expansion, and partner-led deals, so no deal stalls waiting on one person ; Shorten deal cycles by delivering demos that become the internal standard — the kind reps study, replicate, and learn from ; Drive deals to close as a technical co-closer, not just a validator — reinforcing value, navigating gaps with roadmap and vision, and keeping momentum when the answer isn't a clean "yes, today" ; Shape product roadmap by translating field patterns into structured input PMs actually use — and closing the loop back to reps when things ship ; Accelerate Migrate-to-Protect attach by supporting expansion conversations with existing customers and helping AEs and AMs connect the dots between products ; Compound the team's technical leverage by building reusable assets and AI-powered workflows so the same problem stops landing on the team's plate twice. Your team You'll join the AI Sales Enablement team, reporting to the Senior Manager, AI Sales Enablement.

You'll work alongside our existing Technical Sales Specialist and our Sales Enablement function, partnering daily with the SDR, AE, AM, Channel, and Product teams across ShareGate. We're rebuilding what Technical Sales means at ShareGate — from a reactive deal-support function into a builder function that scales the technical capability of the entire sales team. You'll have a direct hand in shaping how this function takes form.

What you'll bring Experience in a customer-facing technical sales role at a B2B SaaS company ; Familiarity with the Microsoft 365 platform (governance, migration, or adjacent experience is a strong plus) ; High business acumen with a track record of influencing deals to close ; Strong demo craft — you treat it as a discipline, not just a deliverable ; A builder mindset: you reach for systems and AI workflows that scale your knowledge rather than trading your own time for every problem ; Genuine AI fluency — comfortable building your own workflows, not just using tools at surface level ; Clear, confident communication across audiences, from IT admin to CIO to partner sales rep (bilingual French/English is a strong asset). Most of this sounds like you? Apply.

What the job comes with Base salary: $90,000–$110,000 CAD + variable.

Technical Sales Specialist - ShareGate