Account Executive

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

📋 Description

• Take ownership of the entire sales process from initial discovery through to closing deals with IT, security, and procurement decision-makers.

• Build and oversee a strong pipeline of new business opportunities using HubSpot.

• Ensure deal hygiene and maintain accurate forecasts.

• Conduct consultative discovery sessions to identify challenges related to Microsoft 365 migration and governance.

• Create compelling business cases for committees comprising multiple stakeholders.

• Develop relationships at various levels within customer organizations.

• Deliver customized demonstrations and proposals highlighting measurable ROI.

• Employ AI tools to enhance qualification, deal analysis, and preparation for objections.

• Collaborate with SDR, partner, and marketing teams to drive top-of-funnel activity and articulate the Migrate + Protect bundle narrative.

• Share insights with the team and assist in the development of the sales playbook.

• Engage in structured deal reviews, provide feedback, and participate in Gong-based debriefs focusing on wins and losses.

⛳️ Requirements

• A minimum of 3 years of full-cycle B2B SaaS sales experience with a demonstrated history of achieving sales quotas.

• Experience in consultative selling, particularly in identifying pain points and constructing business cases.

• Proven ability to manage complex, multi-stakeholder sales processes involving IT, security, and procurement roles.

• Strong discipline in utilizing CRM systems, with a preference for HubSpot.

• Daily proficiency in AI tools within sales workflows, including qualification, deal analysis, and call preparation.

• Familiarity with Microsoft 365 or SharePoint environments, as well as the broader Microsoft ecosystem, is advantageous.

• Experience in a fast-paced SaaS environment where the candidate contributed to shaping the sales playbook is a plus.

🏝️ Benefits

• Long-Term Incentive Plan (LTIP) to participate in Workleap's sustained growth.

• RRSP contribution.

• Comprehensive family health insurance.

• Access to telemedicine services.

• Annual wellness budget.

• Flexible vacation policy.

• Option for remote work with the opportunity to access our Montreal office.

• In-person gatherings held biannually.

• Claude access available for all employees.