Technical Sales Specialist - Workleap

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 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: Own every technical moment in the sales cycle — demos, advanced discovery, evaluation sessions — so prospects never leave a conversation with unanswered questions and no opportunity stalls for lack of technical depth; Shorten deal cycles by delivering demos that become the internal gold standard — showcasing the platform's agentic capabilities in a way reps study, replicate, and learn from; Drive deals to close as a technical co-closer — reinforcing the value of the Workleap Platform and Manager Agent, navigating gaps with roadmap and vision, and keeping momentum when the answer isn't a clean "yes, today"; Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of product and AI conversations independently; Shape the product roadmap by serving as the bridge between the field and product leaders — translating technical objections and field patterns into structured input PMs actually use, and closing the loop back to reps when things ship; Compound the team's technical leverage by building reusable assets and AI-powered workflows — modelling internally the same agentic philosophy we sell to our customers; Accelerate Manager Agent adoption by supporting expansion conversations and helping AEs and AMs articulate the value of our agentic approach compellingly. Your Team 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.