Director, Platform and AI Sales

League
Canada, Toronto
Workplace: RemoteFull timeCAD 175,000 - 200,000 annuallyFunction: SalesEducation: bachelorsSkills: ["Strategic sales leadership","Building executive trust","Forecasting accuracy","Negotiation","Communication"]

Lead enterprise platform and AI solution sales as part of the Go-to-Market team, expanding League’s footprint across Canada. Own the end-to-end sales process, build pipeline via your network, and drive quota attainment through account-based campaigns. Negotiate complex software and professional services agreements, maintain accurate forecasts, and collaborate with Solution Engineering, Partnerships, and Product Marketing to shape buyer journeys and customer partnerships.

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FursaFursa
League
League
3 days ago

Director, Platform and AI Sales

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Source: Company careers pageValidated by: Fursa AI
Last checked: 4 hours agoStatus: Live

Job Summary

Lead enterprise platform and AI solution sales as part of the Go-to-Market team, expanding League’s footprint across Canada. Own the end-to-end sales process, build pipeline via your network, and drive quota attainment through account-based campaigns. Negotiate complex software and professional services agreements, maintain accurate forecasts, and collaborate with Solution Engineering, Partnerships, and Product Marketing to shape buyer journeys and customer partnerships.
Location: Canada, Toronto
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Expand League’s footprint in Canada by building on existing customer relationships
  • •Own the end-to-end sales process for target platform accounts, from strategy and pipeline development through closing and relationship growth
  • •Build pipeline using your network and partner with Business Development and Marketing on account-based marketing campaigns
  • •Meet and exceed sales objectives while maintaining accurate, up-to-date sales forecasts
  • •Negotiate complex software and professional services agreements and create compelling narratives for C-suite stakeholders

Pay and Benefits

Salary: CAD 175,000 - 200,000 annually

Key Requirements

  • •8+ years selling PaaS or SaaS solutions, focused on digital transformation and/or consumer and patient engagement
  • •Proven experience selling AI-powered solutions
  • •Deep healthcare industry knowledge, especially public healthcare services and provincial/territorial health plans
  • •A track record of consistent quota attainment in complex, enterprise sales environments
  • •Proficiency with Salesforce and sales acceleration/enablement tools; Bachelor’s degree in Business or equivalent experience
Education:Bachelor's
Skills:Strategic sales leadershipBuilding executive trustForecasting accuracyNegotiationCommunication
Tech Stack:Salesforce

Company Brief

League
Provides a digital health and benefits platform that connects employers, employees, and healthcare providers to manage benefits, wellness, and virtual care through an integrated consumer-facing experience.
Industry: HealthTech
Company Size: Large (251 to 1,000 employees)
Growth: Scaleup
Headquarters: Toronto, Canada
Founded: 2014
WebsiteLinkedIn