[Hiring] Technical Sales Specialist @Workleap

Role 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 answer isn't a clean "yes, today";
• Shape product roadmap by translating field patterns into structured input PMs actually use — and closing the loop back to reps when things ship;
• Accelerate Migrate-to-Protect attach by supporting expansion conversations with existing customers and helping AEs and AMs connect the dots between products;
• Compound the team's technical leverage by building reusable assets and AI-powered workflows so the same problem stops landing on the team's plate twice.

A typical week? A mix of customer-facing technical sessions where your job is to move deals forward, not just answer questions. Time spent building: training modules, AI workflows, playbooks, reusable assets, so the same problem doesn't land on your plate twice. And real time with Product, surfacing the patterns you're seeing in the field and shaping what gets prioritized. The best version of this week ends with you having done less reactive deal support than the week before, because the system you built last month is now doing the heavy lifting.

What does your future team look like? You'll join the AI Sales & Enablement team, reporting to the Senior Manager, AI Sales & Enablement. You'll work alongside our existing Technical Sales Specialist, our Sales Enablement function, and partner daily with the SDR, AE, AM, Channel, and Product teams across ShareGate.

What are the next challenges awaiting your team? We're rebuilding what Technical Sales means at ShareGate. From a reactive deal-support function into a builder function that scales the technical capability of the entire sales team. You'll have direct hand in shaping how this function takes form.

Qualifications

• 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 — you treat it as a discipline, not just a deliverable;
• A builder mindset: you reach for systems and AI workflows that scale your knowledge rather than trading your own time for every problem;
• Genuine AI fluency — comfortable building your own workflows, not just using tools at surface level;
• Clear, confident communication across audiences, from IT admin to CIO to partner sales rep (bilingual French/English is a strong asset).

Requirements

• Salary range: $90–110k CAD.
• This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.
• As this is a sales role, it is also eligible for commission — bringing the total on-target earnings (OTE) to approximately $100–120k CAD.

Benefits

• At Workleap, we build together, we trust each other, and we support each other in success or failure.
• You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.
• We strive to create a healthy and inclusive work environment. This is everyone’s business.

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, and 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.