Technical Sales Specialist - Workleap

Responsibilities

• 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

Requirements

• Experience in a customer-facing technical sales role at a B2B SaaS company;
• Genuine AI and agentic fluency - comfortable building your own workflows and explaining complex AI concepts to non-technical audiences, without needing a script;
• Strong demo craft - you treat it as a discipline, not just a deliverable, and your demos become the references others copy;
• High business acumen with a demonstrated track record of influencing deals to close (pre-sales, expansion, or both);
• A builder mindset: you reach for systems and AI workflows that scale your knowledge rather than trading your own time for every problem;
• Clear, confident communication across audiences - from HR leaders to C-suite;
• Bonus: familiarity with HR tech, performance management, or employee engagement solutions.
• Most of this sounds like you? Apply.
• What the Job Comes With
• 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 an

Benefits

Additional Information

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.

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