Technical Sales Specialist - 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.

Job Description

So, what will your new role look like?

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.

Responsibilities:

• 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.

A typical week?   

A mix of customer-facing technical sessions where your job is to move deals forward, not just answer questions. Time spent building: training modules, AI workflows, playbooks, reusable assets, so the same problem doesn't land on your plate twice. And real time with Product, surfacing the patterns you're seeing in the field and shaping what gets prioritized. The best version of this week ends with you having done less reactive deal support than the week before, because the system you built last month is now doing the heavy lifting.

What does your future team look like?   

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, our Sales Enablement function, and partner daily with the SDR, AE, AM, Channel, and Product teams across ShareGate.

What are the next challenges awaiting your team?   

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 direct hand in shaping how this function takes form.

Qualifications

• 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).

Salary range: $90–110k CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.
As this is a sales role, it is also eligible for commission — bringing the total on-target earnings (OTE) to approximately $100–120k CAD.

What drives us

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire 

Transparency is how we hire — for you and for us.

Your journey starts with a recruiter conversation, followed by a virtual interview with the hiring manager and one additional interviewer. Next, you'll complete a take-home case study and meet potential teammates to discuss and collaborate on your work. If it's a match on both sides, we move to an offer. Some positions follow a slightly different path — your recruiter will walk you through it on the call if that's the case.

In the spirit of transparency: we use AI to support parts of the process, but every hiring decision remains firmly human.

We're committed to making this an inclusive and thoughtful experience for every candidate. We're looking forward to showing you that.

By applying, you confirm you've read and agree to our privacy policy.

#LI-Remote