Reimagine Work, on behalf of an entrepreneurial couple, is looking for a skilled Property Caretaker to maintain two South Island properties. The successful candidate will be a natural fixer with multiple skills, have the inherent ability to plan, and execute diligent maintenance schedules, and communicate effectively at a high level. 

About the Clients 

Our clients have ties to a network of professionals in finance, legal, construction, and business development. While transitioning to focus more on personal interests, they remain engaged in their professional and philanthropic activities. 

This role offers an opportunity to support a respected family, working closely with their trusted team to provide care, responsibility and maintenance of their homes. 

An example week in the life of the Property Caretaker 

Monday: Respond to non-urgent maintenance communication from Owners. Schedule and complete these tasks or outsource. Complete monthly property walk-throughs. Update property maintenance tracking. 

Tuesday: Clear Victoria property gutters as scheduled with the Owners. 

Wednesday: Decide on paint samples, purchase stocked goods (light bulbs). Schedule and confirm the painting schedule with the owners. 

Thursday: Support the Gardner at both properties. 

Friday: Winterize Oak Bay property (boat, irrigation, etc.) as scheduled with the Owners.

Key Responsibilities 

Administration: 

● Maintain task lists and schedules in an Excel spreadsheet 

● Maintain accurate record keeping, including of purchases, warranties, and guarantees

● Timely and professional communication with property owners, clients, tradespeople and other contractors 

● Manage the procurement process for all equipment and materials 

● Collaborate with the Executive Assistant to ensure that all asset documents are properly maintained with accurate, recent appraisals and competitive quotes

Property Management: 

● Prioritize tasks and maintain schedules for all preventative maintenance and household duties, including performing routine property inspections and providing hands-on maintenance, such as light HVAC, electrical, plumbing, windows, gutters, vehicles, boats, and tool maintenance 

● Conduct routine landscape inspections and hands-on gardens and hardscape maintenance (e.g. leaf removal, outdoor furnishings, irrigation winterizing)

● Oversee, coordinate, and/or work alongside property and landscape contractors as needed (e.g. gardeners, plumbers, auto mechanics, house cleaners) 

● Maintain emergency preparedness and response for weather events, power outages, and security alarms 

● Provide general household support, including minor repairs, pickup and delivery errands, and utility space upkeep/care 

● Maintain meticulous care of tools and work vehicle 

Qualifications: 

● 5+ years' experience in trades, facilities or property maintenance 

● Valid Class 5 Driver's License 

● Skilled in mechanical systems troubleshooting and light carpentry 

● Comfortable lifting 50+ lbs, climbing ladders, and performing physical tasks

● Available for emergency call-outs and occasional weekend/holiday needs

● Live within 30 minutes of Oak Bay 

● Background check required 

Preferred Experience: 

● Certification or licensure in a trade (e.g. electrical, plumbing, HVAC, horticultural)

● Experience in maintaining heritage homes or architecturally detailed properties

● Familiarity with maintenance management systems and smart home technology ● Experience with automotive and/or boat maintenance 

Benefits: 

● Competitive salary: $60,000–$80,000 per year, based on experience ● Monday to Friday, regular hours 9:00 am - 5:00 pm 

● Holiday and Overtime pay 

● Opportunity to work in a stable, respectful environment, taking pride in quiet excellence.

How to Apply 

Please send a resume and cover letter with the subject line ‘Property Caretaker’ to careers@reimaginework.ca. 

We thank all applicants for their interest; however, only those candidates selected for interviews will be contacted.