Account Executive - ShareGate

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: The Workleap Agent, our agentic HR platform that helps managers become better leaders, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

ShareGate is growing fast, and we're building the sales team that takes us further. As an Account Executive, New Business, you own the full sales cycle — from discovery to close — with IT, security, and procurement decision-makers navigating real complexity inside Microsoft 365. This isn't a transactional role. We're looking for someone who can build a business case, navigate a buying committee, and earn the trust of multiple stakeholders across a 60–90 day cycle. And if you have the ambition to match, this role is a clear on-ramp toward an Enterprise motion.

• Build and manage a robust new business pipeline in HubSpot, maintaining deal hygiene and forecast accuracy that the whole team can rely on;
• Lead deep consultative discovery with IT, security, and procurement buyers to surface real M365 migration and governance pain — and build a business case that holds up in front of a buying committee;
• Drive multi-stakeholder sales cycles by developing relationships at multiple levels of the customer organization — not just the champion, but the full buying committee;
• Deliver tailored demos and proposals with measurable ROI that connect ShareGate's value to each prospect's specific environment;
• Integrate AI tools across every stage of the sales cycle — qualification, deal analysis, objection prep — to move faster and decide smarter;
• Collaborate with SDR, partner, and marketing teams to fuel the top of funnel and sharpen the Migrate + Protect bundle narrative;
• Share what you learn with the team to raise the collective bar — we build the playbook together, we don't just execute it.

You'll be joining a team of about ten Account Executives who push each other to get better — not competitively, but in a "we win together" way. The team's manager is a hands-on coach: structured deal reviews, direct feedback, and genuine investment in your development. Week to week, you'll work closely with SDRs on lead quality, partner teams on co-sell opportunities, and your AE peers to debrief wins and losses through Gong reviews. The pace is high. The bar is high. That's exactly what you're looking for.

• 3+ years of full-cycle B2B SaaS sales experience with a proven track record of hitting quota;
• Consultative selling depth — you know how to ask the right questions, uncover real pain, and build a business case that holds up in front of a multi-stakeholder buying committee;
• Experience running complex, multi-stakeholder sales cycles involving IT, security, and procurement profiles;
• Strong CRM discipline — HubSpot preferred — with solid pipeline management and forecasting habits;
• Real, daily AI fluency in your sales workflow (qualification, deal analysis, call prep) — not a beginner, someone who already uses these tools;
• Bonus: familiarity with Microsoft 365 / SharePoint environments or experience in the Microsoft ecosystem;
• Bonus: experience in a high-growth SaaS environment where you helped shape the playbook, not just run it.

Most of this sounds like you? Apply.

• Base salary: $75k to $90k.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.
  • Pay mix: 60% base salary, 40% variable
  • OTE: $125k–$150k
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gathering twice a year.
• Claude access, for everyone.

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

Transparency is how we hire — for you as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

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