TechnicalSalesSpecialist-ShareGate

Company Description 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. Job Description So, what will your new role look like? This isn't the Technical Sales Specialist role of five years ago. We're not looking for someone who just shows up on every technical call. We're looking for a builder. Someone who knows when to jump on a call because the deal demands it, and when to instead build the system, training, or asset that lets a rep handle that same call confidently next time. When you're in a deal, you're not just validating fit. You're reinforcing value, navigating technical gaps with vision and roadmap, and helping close. Responsibilities: Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of technical conversations independently — without routing everything through TSS; Eliminate the single point of failure on technical depth by taking real load off the existing TSS across pre-sales, expansion, and partner-led deals, so no deal stalls waiting on one person; Shorten deal cycles by delivering demos that become the internal standard — the kind reps study, replicate, and learn from; Drive deals to close as a technical co-closer, not just a validator — reinforcing value, navigating gaps with roadmap and vision, and keeping momentum when the answe