Account Executive - ShareGate

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.

Your impact:

• 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.