Technical Sales Specialist - ShareGate

Workleap

Remote regions

Canada

Salary range

$66,138–$80,868/yr

Benefits

Responsibilities:

  • Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement.
  • Shorten deal cycles by delivering demos that become the internal standard.
  • Shape product roadmap by translating field patterns into structured input PMs actually use.

A Typical Week:

  • A mix of customer-facing technical sessions where your job is to move deals forward.
  • Time spent building: training modules, AI workflows, playbooks, reusable assets.
  • Real time with Product, surfacing the patterns you're seeing in the field.

Qualifications:

  • Experience in a customer-facing technical sales role at a B2B SaaS company.
  • High business acumen with a track record of influencing deals to close.
  • A builder mindset: you reach for systems and AI workflows that scale your knowledge.

Workleap

Workleap, founded in 2006, builds simple products that matter to users through its Workleap Agent HR platform and ShareGate, a Microsoft 365 migration and governance solution. The company fosters a culture that values those excited by hard problems and shaping the future.

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