THE OPPORTUNITY
You've sold before. You know how to open doors, run a territory, and close. What you probably haven't had is a product this easy to believe in.
Smartway Trailer Rentals gives manufacturers, distributors, retailers, and logistics operators mobile storage capacity without a warehouse lease. We stage trailers where they're needed, on a monthly basis, at a fraction of the cost of fixed space. As part of the Warehouse on Wheels network — 40+ locations, 37,000+ units, 7,000+ customers across North America — we bring the backing of a continent-wide fleet with the local feel of a Bradford-based team.
We're looking for a Regional Sales Account Manager to own the Bradford / York Region territory — hunting new customers across the Highway 400 corridor and building a book that pays.
WHAT YOU'LL ACTUALLY DO
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Build and execute a prospecting plan for your region — cold calls, cold emails, in-person visits, networking events, trade shows
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Identify and qualify new accounts in manufacturing, retail, distribution, 3PL, food & beverage, agriculture, and adjacent verticals across York Region and Simcoe County
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Run discovery conversations that get to real operational pain (seasonal surges, dock congestion, storage overflow, line changeovers)
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Present solutions — primarily mobile storage, with cartage where it fits — and tie them to the customer's specific situation
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Collaborate with the GM on pricing, onboarding, and account strategy
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Keep HubSpot tight: logged activities, clean pipeline, accurate forecasts
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Track regional trends and competitor activity so you're always a step ahead
WHO WE'RE LOOKING FOR
We're not posting this for someone learning B2B sales. We want someone who's done it — who can walk into a cold account, build credibility fast, navigate multiple stakeholders, and close.
You're likely a fit if:
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You have 5+ years of B2B field sales experience, preferably in equipment rental, logistics, transportation, or industrial distribution
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You've carried and hit a quota — and you have the receipts
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You're comfortable making calls, showing up unannounced, and earning your way in
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You can read a room: you know when to lead with ROI and when to lead with simplicity
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You log your activity in a CRM (HubSpot preferred) because you know a clean pipeline is a better pipeline
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You want autonomy and accountability — not hand-holding
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You know the Bradford / York Region / GTA-North market, or you're ready to learn it fast
COMPENSATION
Base salary $70,000–$80,000 CAD, plus uncapped commission. On-target earnings for a rep hitting quota typically land $100,000–$130,000+ CAD.
The product works. The economics are real — our trailers typically cost 2–4× less than fixed warehouse space. And the sales motion is straightforward: find a company with a capacity problem, show them the math, and make it easy to say yes.
If you want a territory you can build, a product worth selling, and a team that gets out of your way and lets you work — we'd like to talk.
Smartway does not use AI in the hiring process.
Smartway is an equal opportunity employer committed to providing an inclusive and accessible employment experience. In compliance with the Accessibility for Ontarians with Disabilities Act (AODA), accommodations are available upon request throughout the recruitment and selection process. If contacted for an interview, please advise us if accommodations are required.
