Account Executive

This is a fully remote position, open to applicants in Canada.

📋 Description

• Develop and oversee a strong new business pipeline in HubSpot, ensuring deal hygiene and forecast precision that the entire team can depend on;

• Conduct in-depth consultative discovery sessions with IT, security, and procurement buyers to identify genuine M365 migration and governance challenges — and create a compelling business case that stands up before a buying committee;

• Manage multi-stakeholder sales cycles by fostering relationships at various levels within the customer organization — engaging not just the champion, but the entire buying committee;

• Present customized demos and proposals that demonstrate measurable ROI, linking ShareGate's value to each prospect's unique environment;

• Employ AI tools throughout every phase of the sales cycle — qualification, deal analysis, objection preparation — to enhance speed and decision-making;

• Collaborate with SDR, partner, and marketing teams to stimulate the top of the funnel and refine the narrative for the Migrate + Protect bundle;

• Share insights gained with the team to elevate collective performance — we collaboratively develop the playbook, rather than merely executing it.

⛳️ Requirements

• Over 3 years of comprehensive B2B SaaS sales experience with a demonstrated history of achieving quotas;

• Expertise in consultative selling — adept at asking the right questions, uncovering genuine pain points, and constructing a business case that withstands scrutiny from a multi-stakeholder buying committee;

• Proven experience managing complex, multi-stakeholder sales cycles that include IT, security, and procurement profiles;

• Strong discipline in CRM usage — HubSpot preferred — with effective pipeline management and forecasting practices;

• Daily proficiency in AI tools integrated into your sales workflow (qualification, deal analysis, call preparation) — not a novice, but someone already utilizing these tools;

• Bonus: familiarity with Microsoft 365 / SharePoint environments or experience within the Microsoft ecosystem;

• Bonus: experience in a high-growth SaaS setting where you contributed to shaping the playbook, rather than simply executing it.

🏝️ Benefits

• Base salary: $75k to $90k (60% base, 40% variable)

• OTE: $125k–$150k

• LTIP program, allowing participation in Workleap's long-term growth.

• RRSP + Family health insurance + telemedicine + annual wellness budget.

• Flexible vacation policy.

• Remote work option, with access to our Montreal office.

• In-person gatherings twice a year.

• Claude access for all employees.