Account Executive

Workleap

Account Executive managing full sales cycle for ShareGate's Microsoft 365 solutions. Engaging with IT, security, and procurement decision-makers to drive business growth.

Posted 7/13/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$75,000 - CA$90,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in full-cycle B2B SaaS sales, with a focus on consultative selling and multi-stakeholder engagement. Proficient in utilizing HubSpot for pipeline management and integrating AI tools to enhance sales processes.

Highest-signal resume keywords

B2B SaaS Sales ExperienceConsultative SellingHubSpot CRM ProficiencyAI Tool IntegrationMicrosoft 365 Familiarity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Full-Cycle SalesPipeline ManagementForecastingDeal AnalysisConsultative Discovery

Soft Skills

Relationship BuildingCollaborationCommunication

Tools & Technologies

HubSpotAI ToolsMicrosoft 365SharePoint

Industry Keywords

B2B SalesSaaSMulti-Stakeholder Sales CyclesIT ProcurementSales Cycle Management

About the role

Key responsibilities & 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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

Base salary: $75k to $90k (60% base, 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.