--- Showing Agent (Full Time)4-Day Workweek: 52 Long Weekends a Year ---
You want a real career, not just “a job.” You want to learn a business, get into a professional office environment, and grow. You also want your life back.
This role is the entry point into a full-time office career in property management, with a clear growth path inside Upper Edge.
Schedule that actually changes your life:
- Monday to Thursday
- 10:00 am to 8:30 pm
- 40 hours per week
- THREE DAYS off every week
- 52 long weekends a year
You have always pictured yourself in an office career, but you need the right first step to get in. THIS IS THAT STEP.
We are hiring a full-time Showing Agent to be the face of our rental properties. You will drive to our managed properties, meet prospective tenants, and run professional showings that help great residents find their next home.
If you are in your 20’s (or you simply relate to the vibe), love being out and about, enjoy people, and want a clear path into a stable, full-time office career, this is built for you.
THE CAREER PATH (This is not a dead-end job)
This role is designed as a stepping stone into our property management team:
- Showing Agent (you start here): learn the business, the properties, and how leasing works, Perform some light data entry duties around the office.
- Property Management Assistant: move into office-based operations and resident communication
- Property Manager: manage a portfolio and performance
- Senior Property Manager: leadership, strategy, investor experience
Your performance in showings, communication, and follow-through determines how quickly you move up.
WHAT YOU'LL DO
You are the person who turns “I saw the ad” into “I want to apply.”
CORE RESPONSIBILITIES:
- Drive to rental properties and conduct scheduled showings
- Deliver a great tenant experience: friendly, confident, professional
- Answer basic questions about the unit, neighborhood, and application process
- Report feedback after showings so our team can improve ads, pricing, and presentation
- Coordinate with our office team to keep the showing calendar tight and efficient
YOU'RE A FIT IF YOU ARE
This role is perfect if you are:
- Outgoing and confident: comfortable meeting new people daily
- Reliable and disciplined: you show up on time, every time
- Observant and detailed: you notice issues in a unit and communicate them
- Motivated and organized: you can manage your day and move fast
- Tech-comfortable: you can learn our systems quickly
ABOUT US
Upper Edge Property Management is a progressive, tech forward company serving Winnipeg since 1997. Our vision is to improve the lives of 1 million property owners and renters. Our core values guide how we hire and how we work: inspirational, disciplined, accountable, transparent, aligned, and results oriented.
WHAT'S IN IT FOR YOU
- Full-time role with real career progression
- Daily variety: you are not stuck at a desk all day
- Hands-on training in leasing and property management workflows
- A company with defined roles and growth track (Showing Agent - PMA - PM - Senior PM)
REQUIREMENTS
- Valid driver’s license and reliable vehicle (you will be driving to show properties)
- Strong communication and professionalism in person
- Eligible to work in Canada
EXPERIENCE
- Experience in hospitality preferred
- Minimum typing speed of 50 words per minute
PHYSICAL REQUIREMENTS
● Must have own vehicle and a valid driver’s license
COMMITMENT TO DIVERSITY
As an equal opportunity employer committed to meeting the needs of a multigenerational and multicultural workforce, Wong Capital and Upper Edge recognize that a diverse staff, reflective of our community and the people we serve, is an integral and welcome part of a successful and ethical business. We hire local and remote talent at all levels regardless of race, colour, religion, age, national origin, gender, gender identity, sexual orientation, or disability, and actively foster inclusion in all forms both within our company and across interactions with clients, candidates and partners.
CHECK US OUT AT
● Upper Edge Website: https://www.winnipegpropertymanagement.ca/about-us/
● Garret Wong Homepage: https://www.garretwong.com
● Garret Wong YouTube Channel: https://www.youtube.com/channel/UCRs3SSmwVFbR2QEjIDqU0Ug
● Instagram: https://www.instagram.com/garretwong.rei/
● Linkedin: https://www.linkedin.com/in/garret-wong-33197913/
● Facebook: https://www.facebook.com/garret.wong.54
● Upper Edge Capital Corp: http://www.upperedgecapital.com
● Spotify: https://open.spotify.com/show/6dFur2VK9EW77hMc5Z1SyZ?si=7e17bcc9919c49a5
● Apple Podcasts: https://podcasts.apple.com/gb/podcast/investing-to-win/id1672816345
● The Rent It Yourself Community:
NEXT STEPS
If this opportunity excites you and you consider yourself hardworking, dedicated, and client-focused, we’d love to hear from you.
Along with your video and resume, please include a cover letter that briefly outlines:
- Your relevant qualifications and work experience.
- Why you believe you’re a strong match for this role and our team.
- Your availability to start and your expected remuneration.
Important: Applications without a video or cover letter may not be reviewed.
We thank all applicants in advance for their interest in joining Upper Edge Property Management.
By applying, you confirm that you are eligible to work in Canada.
Job Types: Full-time, Permanent
Pay: $37,500 per year
Benefits:
- Health Spending Account, HSA and Wellness Account
- On-site parking
Flexible language requirement:
Schedule:
- Day shift
- Monday to Thursday
- No weekends
Application question(s):
- Are you experienced in Google Suite software applications (Sheets, word doc, etc)?
- Minimum typing speed is 50 WPM. What is your typing speed? In case you do not know, https://www.typingtest.com offers free online testing.
Education:
- Secondary School (preferred)
Experience:
- Customer Service/Communication/Hospitality: 2 years (preferred)
- Property management: none, we will train you!
Work Location: In person
Pay: From $37,500.00 per year
Benefits:
- Company events
- Dental care
- Employee assistance program
- Extended health care
- Mileage reimbursement
- On-site parking
- Paid time off
- RRSP match
- Wellness program
Work Location: In person
