Technical Sales Specialist

Workleap

Remote regions

Canada

Benefits

Unlimited PTO

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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."

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.

Compensation:

  • Base salary: $90–110k CAD, with total on-target earnings (OTE) approximately $100–120k CAD.
  • LTIP program, RRSP, family health insurance, telemedicine, and annual wellness budget.
  • Flexible vacation policy and remote work with access to our Montreal office.

Workleap

Workleap is a Montreal-based tech company that builds simple HR and productivity software, including the Workleap Agent and ShareGate, used by over 15,000 companies. The team values builders and intentional growth, focusing on impact and iteration.

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