Fair Fast jobs in Winnipeg, MB

Exterior Cleaning Technician — Roofs, Ladders, Overtime

Fair Warning: Most people who apply for this job do not last. We would rather you figure that out now than during week three.

This is physical, outdoor work done primarily on ladders and roofs in whatever weather the day brings. Rain doesn’t cancel work, it shifts it, often onto your Saturday. The weather runs our schedule, which means weekends and overtime are a regular part of the season.

If that sounds like too much, feel free to close this posting now. No hard feelings.

We also run a longer hiring process than most companies and that is on purpose.

A Day in the Life

• Early Start: Loaded and rolling early every morning.
• Height Work: On 28-foot and 32-foot ladders and sloped roofs for hours at a time. Most days, not occasionally.
• Physical Labor: Hauling ladders, hoses, and heavy gear around properties all day long.
• Weather Extremes: Working in +30°C sun on a roof in July, or cold, wet mornings in spring and fall.
• Repetition & Quality: Performing the exact same motion, done right, hundreds of times.
• Customer Service: Interacting professionally with homeowners who are watching while you work.

Hours & Seasonality

• Weekly Schedule: 35 to 45 hours per week on average, with overtime during peak season.
• Weekend Availability: Weekend work is mandatory when weather forces schedule shifts (e.g., a rained-out Tuesday becomes a working Saturday). You must be genuinely available without conditions.
• Season Length: The main season runs until the first hard freeze (typically late October). Christmas light installations extend into November for technicians who earn that work.
• No Guesswork: You will know exactly where you stand long before the season ends.

Is This Role Right for You?

This IS you if:

• You’ve done this work and want a company that operates professionally.
• You value consistency over raw talent and show up the same every day.
• You make smart, independent decisions when site conditions change.
• You’d rather be outside moving than sitting at a desk.
• You take personal pride when a job isn't done right.

This IS NOT you if:

• Heights make you uneasy ("I’ll get used to it" is an auto-decline).
• You need a predictable 9-to-5 weekly schedule.
• You need step-by-step instructions all day long.
• You want to coast or do the bare minimum.
• You dislike physical labor in changing weather conditions.

> Note: Age is not a factor and experience is welcome, but attitude is the one thing we cannot train.

Pay & Progression

• Starting Pay: $20.00 – $22.00 / hour (based on experience). Paid biweekly.
• 90-Day Review: Performance-based pay review tied to results, not just time served.
• Earning Potential: $27.00 – $28.00 / hour reachable with performance bonuses and revenue share once producing.
• Tips: 100% of client tips go directly to you.
• Overtime: Fully paid overtime during peak periods.

About Our Company

We are three seasons in, growing fast, and building something long-term. The people who join us now are the ones who will run operations in the future.

You don't need to perform a fake personality here, just show up as yourself and do great work. If you want a clear path to run your own crew within two years, that opportunity is real: every lead position in our company was earned internally based on performance numbers.

Our Core Values

• Relentless Improvement: Better than we were last season, every single season.
• To Serve: The homeowner’s experience is part of the job, not a distraction from it.
• Ownership: You handle the issue; you don't pass it along.
• Curiosity: Ask why it’s done that way, then find a better way.
• Balance: We work hard while on the clock, then we go home.
• Respect: For the client, the property, your crew, and everyone's time. Being on time is the first way you show it.

What We Provide

• Paid training and all necessary professional equipment (you don't buy gear).
• Full-time seasonal hours with consistent overtime opportunities.
• Clear progression: Level certifications and internal promotions.
• Winter transition: Christmas light installation opportunities for proven performers.
• Reputation: 207 five-star reviews backing you up on every job site.

Non-Negotiable Requirements

You must meet all of the following criteria to be considered:

• [ ] Valid driver’s license and a clean driving record.
• [ ] Comfortable working at heights: 28-foot ladder experience (2-storey homes) and sloped roof walking. (We train up to 32 ft).
• [ ] Physical stamina: Ability to repeatedly lift and carry 50 lbs throughout a full shift.
• [ ] Location: Residing within 30 minutes of Winnipeg.
• [ ] Full Availability: Available for the complete season, including overtime and weather-dependent weekends.
• [ ] Responsiveness: Highly reachable via phone/text for scheduling.
• [ ] Criminal record check. All offers are conditional on a clean criminal record check. We are in people's homes and yards, and we do not make exceptions on this.

How to Apply & Hiring Process

To apply, submit your resume and answer the screening questions on this posting.

Note: We read your screening answers before your resume. Applications without screening responses will be automatically skipped.

What Happens Next:

• Short Phone Call: We walk through the tough parts of this job in detail so you can decide if it's for you.
• Interview: We meet in person to discuss company goals, expectations, and culture fit.
• Paid Ride-Along: A real day on active job sites with the crew. You test the job; we test your fit.
• Start Date: August 3rd (Non-negotiable start date. Please be prepared to complete the hiring steps quickly).

Pay: $20.00-$28.00 per hour

Benefits:

• Company events

Application question(s):

• What's the highest you've ever worked off the ground, and how did you feel doing it?
• Rain moves our work into evenings and weekends, and the season runs hard until the end of October. What part of your life does that create a problem with? Be honest "nothing" is usually a lie.
• Read our values in the job description. Which one would you actually struggle with, and why?

Work Location: In person