Account Executive - ShareGate

Workleap; Canada; On-site; CAD 75,000 - 90,000; Full time

Benefits offered by this job

LTIP program

RRSP and health insurance

Telemedicine

Annual wellness budget

Flexible vacation policy

Remote work with Montreal office

In-person gatherings twice a year

Claude access

Job summary

ShareGate is growing fast and building a sales team that scales. 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 in Microsoft 365.

You’ll build a robust pipeline in HubSpot, surface business pain, and craft compelling ROI-based proposals for a buying committee. The role emphasizes collaboration with SDRs, partners, and marketing while embracing AI-enhanced sales tools.

Qualifications

• 3+ years of full-cycle B2B SaaS sales with quota attainment.
• Consultative selling that surfaces real business pain.
• Experience running multi-stakeholder IT/security/procurement cycles.
• Strong CRM discipline with forecasting habits.
• Fluency with AI in the sales workflow.
• Bonus: experience with Microsoft 365/SharePoint.
• Bonus: prior high-growth SaaS playbook exposure.

Responsibilities

• Own the full sales cycle from discovery to close with a 60–90 day cycle.
• Lead deep consultative discovery with IT, security and procurement buyers.
• Develop relationships across buying committees and stakeholders.
• Deliver tailored demos and ROI-based proposals.
• Integrate AI tools across qualification, analysis and prep.
• Collaborate with SDRs, partners and marketing to fuel pipeline.
• Share learnings with the team to raise the playbook.

Skills

B2B SaaS sales

Consultative selling

Multi-stakeholder selling

HubSpot CRM

AI in sales workflows

Microsoft 365 familiarity

Relationship building

Tools

HubSpot

Gong

Job description

Your Role

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.

Your Team

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.

What You'll Bring

• 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?

What the Job Comes With

• 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.