Technical Sales Specialist - Workleap

3 weeks, 2 days ago
Full-time
Senior
Customer and Technical Support
Workleap

Workleap

Workleap provides a comprehensive employee engagement software platform designed to enhance the productivity and collaboration of hybrid teams through tools for talent management, performance management, recognition, and onboarding.

Internet Software & Services
251-1K
$93M raised

Description

  • Own technical moments throughout the sales cycle, including demos, advanced discovery, and evaluation sessions.
  • Deliver demos that set the standard for the sales team and help shorten deal cycles.
  • Act as a technical co-closer by reinforcing value, navigating roadmap discussions, and maintaining deal momentum.
  • Lead the technical track of sales onboarding and ongoing enablement to reduce rep ramp time.
  • Serve as the bridge between Sales and Product by translating field objections and patterns into product feedback.
  • Build reusable assets and AI-powered workflows that scale technical knowledge across the team.
  • Support expansion and adoption conversations for Manager Agent and the Workleap Platform.
  • Collaborate with AEs, AMs, SDRs, sales leadership, and product leaders to move deals forward and shape the function.

Requirements

  • Experience in a customer-facing technical sales role at a B2B SaaS company.
  • Genuine AI and agentic fluency, including the ability to build workflows and explain complex AI concepts to non-technical audiences.
  • Strong demo craft with the ability to create reference-quality demos.
  • Demonstrated track record of influencing deals to close in pre-sales, expansion, or both.
  • High business acumen and comfort navigating technical and commercial discussions.
  • A builder mindset focused on systems and AI workflows that scale knowledge.
  • Clear, confident communication across audiences from HR leaders to C-suite executives.
  • Familiarity with HR tech, performance management, or employee engagement solutions is a plus.

Benefits

  • Base salary of $90k to $110k CAD, with commission bringing total on-target earnings to approximately $100k–120k CAD.
  • LTIP program with long-term growth participation.
  • RRSP plus family health insurance, telemedicine, and an annual wellness budget.
  • Flexible vacation policy.
  • Remote work with access to the Montreal office.
  • In-person company gatherings twice a year.
  • Claude access for everyone.

Interested in this position?

Apply directly on the company website

Apply Now

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