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.

What You'll Bring

• 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

• Base salary: $90to $110k . 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.


• 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 as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

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