Account Executive

Workleap

Account Executive selling ShareGate, Workleap’s Microsoft 365 migration and governance software. Owning complex B2B SaaS sales cycles from discovery through close with IT, security, and procurement buyers.

Posted 8/14/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$75,000 - CA$90,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in full-cycle B2B SaaS sales, with a focus on consultative selling and building business cases for multi-stakeholder environments. Proficient in utilizing AI tools and HubSpot for pipeline management and deal analysis.

Highest-signal resume keywords

Full-Cycle B2B SaaS Sales ExperienceConsultative SellingHubSpot CRM ProficiencyAI Fluency in Sales WorkflowsMicrosoft 365 Familiarity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Cycle ManagementDeal AnalysisBusiness Case DevelopmentForecast AccuracyPipeline Management

Soft Skills

Relationship BuildingCollaborationConsultative DiscoveryCommunication

Tools & Technologies

HubSpotAI ToolsGong

Industry Keywords

B2B SalesSaaSIT Decision-MakersSecurity Decision-MakersProcurement Decision-Makers

About the role

Key responsibilities & impact

Own the full sales cycle from discovery to close with IT, security, and procurement decision-makers
Build and manage a robust new business pipeline in HubSpot
Maintain deal hygiene and forecast accuracy
Lead consultative discovery to uncover Microsoft 365 migration and governance pain
Build business cases for multi-stakeholder buying committees
Develop relationships across multiple levels of customer organizations
Deliver tailored demos and proposals with measurable ROI
Integrate AI tools into qualification, deal analysis, and objection preparation
Collaborate with SDR, partner, and marketing teams to fuel the top of funnel
Share learnings with the team and contribute to the sales playbook
Work with SDRs on lead quality, partner teams on co-sell opportunities, and Account Executive peers through Gong reviews

Requirements

What you’ll need

3+ years of full-cycle B2B SaaS sales experience with a proven track record of hitting quota
Consultative selling experience, including uncovering pain and building business cases
Experience running complex, multi-stakeholder sales cycles involving IT, security, and procurement profiles
Strong CRM discipline, with HubSpot preferred
Daily AI fluency in sales workflows, including qualification, deal analysis, and call preparation
Familiarity with Microsoft 365 / SharePoint environments or the Microsoft ecosystem is a bonus
Experience in a high-growth SaaS environment and helping shape the playbook is a bonus

Benefits

Comp & perks

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