About the role
Company Description
Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: The Workleap Agent, our agentic HR platform that helps managers become better leaders, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.
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. 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. Total on-target earnings (OTE) approximately $100,000–$120,000 CAD ;
- LTIP program, share in Workleap's long-term growth.
- RRSP + Family health insurance + telemedicine + annual wellness budget.
- Flexible vacation policy.
- Remote work, with access to our Montreal office.
- In-person gathering twice a year.
- Claude access, for everyone.
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.
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