Customer Support jobs in Canada

Workleap is a Montreal-based tech company on a mission to make work simpler.

Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.

Workleap operates two distinct product lines:

• The Workleap Platform , an AI-powered HR solution designed to drive team performance and boost employee engagement.


• ShareGate , the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.

We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.

As a Small Business Account Executive at Workleap, you’ll be a key player in accelerating revenue growth by bringing our mission-led products to more teams. This is a sales role where consultative selling, strategic thinking, and relationship-building meet to create serious impact. There will be components of full funnel work; in 95% of the case you’ll be owning the client relationship from Product Demo to Close and helping redefine how companies experience work—one conversation at a time.

Responsibilities:

• Manage and close new business opportunities in our SMB segment


• Own your pipeline from end to end— qualifying, demoing, negotiating, and closing;


• Lead thoughtful, strategic discovery calls that align with buyer objectives and uncover pain points;


• Deliver customized demos and business cases that speak to both technical and non-technical audiences;


• Partner closely with SDRs and Marketing to support pipeline development and ABM strategies;


• Collaborate cross-functionally with Product and Customer Success to keep value delivery on point;


• Maintain strong pipeline hygiene and forecasting accuracy in HubSpot;


• Stay sharp through weekly deal reviews, coaching sessions, and enablement initiatives.

You might kick off your Monday refining deal strategy with your SDR , run a discovery call with a prospective customer in Montréal, jump into a feedback sync with the Product team, and close the week by helping a peer prep for a big demo. Every week is different—but always driven by impact, collaboration, and growth.

This is a space where bold thinking is welcomed, autonomy is encouraged, and wins are shared. You’ll have the chance to take ownership, shape how we engage the Francophone market, and continuously test and evolve how we sell.

Within your first year, you’ll become a trusted closer for our SBM deals, and help us refine how we discover, demo, and sell value. You’ll be a go-to for strategic deal collaboration, coaching peers, and contributing to how we continuously improve as a team.

What does your future team look like?

You’ll join a passionate, high-performing sales team that loves to win together. We’re curious, collaborative, and motivated by the real-world impact our solutions bring to modern workplaces. Everyone brings a unique perspective, and we believe we grow stronger when we learn from each other.

At Workleap, we lead with transparency and kindness—we’re big on open communication, supporting each other through challenges, and celebrating the big (and small) wins. We don’t do average—we build and sell products that truly improve how people experience work.

What are the next challenges awaiting your team?

We’ve acquired new products to sell and have redefined our target markets. Unlocking the keys to success in these new areas is top of mind and our #1 challenge these days as it will drive the future of the business.

• 1-2 years of SaaS sales closing experience;


• Strong consultative selling skills and value-based sales approach;


• Proven success with multi-stakeholder deal cycles;


• Excellent demo delivery and executive-level communication skills;


• Experience with pipeline management and forecasting (HubSpot is a bonus);


• Self-starter mindset in a fast-paced, evolving environment.


• Fluency to speak & sell in French;

Assets:

• Background in HR tech, employee experience, or productivity SaaS;


• Experience with tools like Gong, Showpad, and LinkedIn Navigator;


• Exposure to multi-product platforms, integrated solution selling;


• Curious and adaptable mindset — you’re not afraid to test and adopt new AI-driven strategies or tools to optimize your process.

Salary range: $67–$80k CAD.
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.

We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.

Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.

We strive to create a healthy and inclusive work environment. This is everyone’s business.

Our Candidate Experience Flow atWorkleap:
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

We are looking forward to getting to know you!
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