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.
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 the technical authority of the entire sales organization — someone who understands our agentic platform deeply, speaks the language of AI fluently, and knows when to jump on a call because the deal demands it, and when to step back and build the system, training, or asset that lets a rep handle that same conversation confidently next time. When you're in a deal, you're not just validating fit — you're the technical voice that builds trust, reinforces value, and helps close.
Your impact:
You'll join the Workleap Sales team, reporting to the Sales Manager. You'll be the bridge between Sales and Product — working closely with product leaders to stay sharp on our agentic roadmap, and with AEs, AMs, and SDRs to translate that expertise into closed deals. We're building Workleap's technical sales function from the ground up — and you'll be one of its architects. As our platform evolves into a fully agentic solution, technical expertise in the sales cycle becomes central. You'll have a direct hand in shaping how this function takes form, particularly around Manager Agent and positioning our AI vision with prospects.
Most of this sounds like you? Apply.
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.
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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Based on 5,577 disclosed Sales salaries on RoleSuite, the role pays a median of $123K/year, with most offers between $83K and $170K (10th–90th percentile: $65K–$230K).
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