About The Position

This role is for a Technical Sales Specialist at Workleap, focusing on the ShareGate product line. The position is not a traditional technical support role but rather a 'builder' role. The specialist will be responsible for developing systems, training, and assets to empower sales representatives to handle technical aspects of deals independently. The goal is to reinforce value, navigate technical gaps, and contribute to closing deals, while also shaping the product roadmap and improving the efficiency of the sales team through scalable solutions and AI workflows.

Requirements

  • Experience in a customer-facing technical sales role at a B2B SaaS company.
  • Familiarity with the Microsoft 365 platform (governance, migration, or adjacent experience is a strong plus).
  • High business acumen with a track record of influencing deals to close.
  • Strong demo craft, treating it as a discipline.
  • A builder mindset, prioritizing scalable systems and AI workflows over trading personal time.
  • Genuine AI fluency, comfortable building own workflows.
  • Clear, confident communication across various audiences (IT admin to CIO to partner sales rep).
  • Bilingual French/English is a strong asset.

Responsibilities

  • Own the technical track of sales onboarding and ongoing enablement to reduce rep ramp time.
  • Eliminate the single point of failure on technical depth by supporting pre-sales, expansion, and partner-led deals.
  • Deliver standard-setting demos that reps can study and replicate to shorten deal cycles.
  • Act as a technical co-closer, reinforcing value, navigating gaps with roadmap and vision, and maintaining deal momentum.
  • Translate field patterns into structured input for Product Managers and close the loop back to reps on product updates.
  • Support expansion conversations with existing customers and help connect the dots between products.
  • Build reusable assets and AI-powered workflows to increase the team's technical leverage and reduce repetitive tasks.

Benefits

  • Commission eligibility
  • Opportunity to express yourself, evolve, and develop creativity
  • Environment that adapts to daily life and needs
  • Healthy and inclusive work environment
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