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The Skyline Group of Companies

Manages property and clean energy investments

Property Manager

Full-TimeUpdated on 10/24/2026
CA$75k/yr+ Car allowance
Mid, Senior
Windsor, ON, Canada
In PersonVisits multiple properties across the region; on-call requirement.
Real EstateReal Estate Property Management

About the job

Requirements
  • Three to five years of property management experience, including residential operations and tenant relations, and availability to be on-call.
  • Knowledge of the Residential Tenancies Act and Landlord and Tenant Board processes.
  • Experience coaching, supporting, and motivating teams.
  • Financial acumen, including experience with invoices, operating expenses, and budget adherence.
  • Communication, customer service, and conflict-resolution skills.
  • Organizational and problem-solving abilities, including prioritizing multiple responsibilities in a fast-paced environment.
  • Proficiency in Microsoft Office and property management software, or ability to learn and adapt to new technology quickly.
  • A valid driver's licence, reliable vehicle, insurance, and ability to travel to properties across the region.
  • Excellent written and verbal English communication.
Responsibilities
  • Lead day-to-day operations of a portfolio of residential properties, ensuring resident experiences and building performance.
  • Oversee property budgets, operating costs, capital projects, and vendor contracts to maximize efficiency and value.
  • Manage on-site teams through leadership and coaching to drive results and employee success.
  • Ensure properties remain well-maintained and compliant through regular inspections and adherence to health and safety standards.
  • Drive tenant retention by fostering positive tenant relationships, proactively addressing concerns, and delivering an exceptional living experience that encourages long-term tenancy.
  • Respond to site emergencies and work with internal teams, contractors, and community partners to support operational excellence.

About the company

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The Skyline Group of Companies

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Skyline Group of Companies acquires, develops, and manages Canadian real estate and clean energy assets for tenants and private investors. Its portfolios cover apartments, industrial buildings, retail properties, and renewable energy infrastructure, with operating businesses handling property management and real estate development in-house. Skyline Wealth Management sells the group's private investment products, while the assets generate income through property rents and energy production; Skyline Mortgage Financing also arranges commercial real estate financing. The privately held group was founded in 1999 and is headquartered in Guelph, Ontario.

Company Size

501-1,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Guelph, Canada

Founded

1999

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Simplify's Take

What believers are saying

  • Operations pay has a stated floor: Skyline's Elmira Plant Operator I role starts at CAD30 per hour.
  • Wealth sales pay has a fixed base: Skyline's Ontario Relationship Manager role advertises CAD60,000 plus uncapped commissions.
  • Solar operations expanded: Skyline's renewable infrastructure fund increased installed solar capacity 83% through its September 2026 acquisition.

What critics are saying

  • Weekend coverage is required: Skyline's Brantford live-in Resident Manager role includes rotating schedules and on-call availability.
  • Wealth sales have a licensing gate: Skyline Relationship Managers need eligibility for registration to sell exempt-market investment products.
  • Housing is part of compensation: Skyline's Brantford Resident Manager package counts apartment rent toward its advertised annual pay.

What makes The Skyline Group of Companies unique

  • Founder leadership continues: Skyline's three co-founders still actively run the group.
  • Retail leasing targets smaller cities: Skyline Retail focuses on service-oriented national brands in secondary and tertiary communities.
  • Energy income is contracted: Skyline Clean Energy Fund buys assets backed by long-term government or private purchase agreements.

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