watsonexteriors.com
Careers — Est. 2016
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watsonexteriors.com
403 477 3935 devon@watsonexteriors.com Hiring in Winnipeg & Manitoba
Completed exterior renovation by the Watson Exteriors crew

Now hiring · Manitoba · Saskatchewan · Alberta

Careers

We're growing across the prairies — salespeople in Winnipeg and Regina, and experienced siding, roofing, window and gutter crews wherever there's steady work. Sales roles come with full paid training on the products and the process.

Currently hiring

Salespeople &
experienced crews
0

Provinces we work in

0+

Projects completed

0

Years in business

0

Roles open now

Open positions

Roles open
right now.

Sales roles in Manitoba and Saskatchewan, plus ongoing contract work for experienced crews. Everything below is the actual scope. If one fits, call or text and we'll set up a conversation the same week.

Exterior renovation salesperson

Winnipeg / Manitoba

You'll meet homeowners at booked appointments, walk the exterior with them, and explain what their siding or roof actually needs. We supply full product training and estimating support — you bring the professionalism and the conversation.

  • Location Winnipeg / Manitoba
  • Compensation Performance-based
  • Schedule Flexible
  • Training Paid, in full
  • Background Sales or customer-facing
  • Start Booking now

Exterior renovation salesperson

Regina / Saskatchewan

Same role, new territory. We're opening up Regina and want someone on the ground who can run booked appointments and represent the company properly at the kitchen table. Full training provided.

  • Location Regina / Saskatchewan
  • Compensation Performance-based
  • Schedule Flexible
  • Training Paid, in full
  • Background Sales or customer-facing
  • Start Booking now

Experienced exterior crews

Siding · Roofing · Windows & doors · Gutters

We're always looking for more experienced crews to take on work across Alberta, Saskatchewan and Manitoba. Siding, roofing, windows and doors, and gutters — steady year-round volume around Calgary, Chestermere, Airdrie, Okotoks, Cochrane, Strathmore and Langdon, for crews who show up, finish clean and stand behind the work.

What you need to have
  • WCB coverage in good standing
  • Valid GST number
  • Liability insurance
  • Minimum 5 years experience for crew leads
  • Own tools and transport
  • Trades Siding, roofing, windows & doors, gutters
  • Territory Alberta, Saskatchewan & Manitoba
  • Engagement Contract crews
  • Volume Ongoing, year-round
  • Experience Crew leads 5+ years
Pay

Performance-based earning

What you make tracks the work you do. No drawn-out ramp before the first cheque.

Pay

Rewarded per appointment

You're paid on every appointment you run as well as the work you close. We'll walk through the full structure on the call.

Time

Flexible schedule

Set your own week around bookings. Plenty of people here run this alongside family or a second commitment.

Start

Paid training

You get paid while you learn the products, the pitch and how an exterior actually goes together.

Growth

Advancement opportunities

Strong performers move into closing, then into running their own area as we grow through Manitoba.

Growth

Room to earn more

No cap on the top end and no territory cannibalising. The more homeowners you help properly, the more you take home.

Siding installation completed by the Watson Exteriors crew
2016 Family-run
ever since

Who we're looking for

Personality first.
We teach the rest.

We've hired servers, tradespeople, students and career salespeople. The ones who do well all share the same handful of traits.

  • 01Outgoing — comfortable starting the conversation
  • 02Confident — you can hold your ground on price
  • 03Self-motivated — nobody chases your calendar for you
  • 04Reliable — homeowners are waiting at the appointment time
  • 05Coachable — you take the feedback and use it next door
Full training provided

You don't need a roofing or construction background to start — we train you properly on the products, the process and how to represent the company on site.

Already sold before?

If you've got real sales experience, you may be able to move directly into a closer role instead of starting at the front end.

How hiring runs

Three steps, same week.

Step 01

Send your details

Fill in the form below or text us. A couple of lines about yourself is plenty — no formal resume needed.

Step 02

Quick conversation

A short call to walk through the role, the territory and how the pay structure actually works in a normal month.

Step 03

Paid training, then appointments

You learn the products and the walkthrough with us, then start running booked appointments.

Apply

Tell us a bit
about yourself.

Send it through and Erik or one of the sales team will follow up with next steps. Prefer to talk? Call or text — that works just as well.

Where we work

AlbertaSaskatchewanManitobaCalgaryChestermereAirdrieOkotoksCochraneStrathmoreLangdonWinnipegRegina
Request Form

Common questions

Before you apply.

Do I need a construction background for the sales roles?

Not to start. You'll be trained properly on the products, the walkthrough and how to read what a home actually needs before you're in front of a homeowner on your own. What we look for is professionalism, reliability and a willingness to learn the trade. Crew roles are different — those need real experience and a five-year crew lead.

How does the pay work?

It's performance-based rather than salaried — you're rewarded for the appointments you run and the work you close, with no cap on the top end. Training is paid. We'll go through the full structure and what a realistic first, third and sixth month looks like on the call.

Is this full time?

The schedule is flexible. Some people run it full time, others fit it around existing commitments. What matters is showing up reliably for the appointments you take on.

I've sold before — do I still start at the bottom?

Not necessarily. If you bring genuine sales experience, you may be able to move directly into a closer role. Mention it in your application and we'll talk it through.

Which areas are you hiring in?

Sales roles are open in Winnipeg and Regina. Crew work runs across all of Western Canada — Alberta, Saskatchewan and Manitoba — with Calgary, Chestermere, Airdrie, Okotoks, Cochrane, Strathmore and Langdon as our steadiest ground. If you're elsewhere in the three provinces, send a general application and we'll keep you on file.

What do crews need before they can take work?

WCB coverage in good standing, a valid GST number and liability insurance — those three are non-negotiable before a crew steps on one of our sites. Crew leads need at least five years in the trade. Bring those and we can talk about volume.

Who will I be dealing with?

Erik and the sales team handle hiring conversations and day-to-day contact. Devon set the standards the company works to and makes sure crews and staff hold to them, but he isn't the one running the calls.