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cs@sspgroup.com8401 5 Side Rd, Milton, ON L9T 2Y7

Careers

Build a Career in Disciplined Freight Operations.

Join a team where ownership, safety, and operating discipline define daily execution. Whether you are on the road or in operations, we provides the structure, support, and accountability required for long-term growth.

Clear expectations
Safety-led decisions
Strong dispatch and ops support

Why SSP

High Standards. Real Operating Support.

We run freight with clear expectations, direct communication, and accountable follow-through. The result is an operating environment where execution quality is supported, measured, and consistently recognized.

Safety as a Core Value

Training, maintenance, and operating checks designed to protect people, freight, and public roadways.

Operational Clarity

Structured workflows and clear handoffs reduce ambiguity so teams can execute with confidence.

Dedicated Support Infrastructure

Dispatch and operations teams work as partners, resolve issues quickly, and keep commitments visible.

Structured Career Growth

Ownership and consistency are rewarded. As We grow, high performers gain broader scope and leadership opportunities.

Fleet Operations

Driver Opportunities

We operate a safety-first fleet backed by structured dispatch and operational support. If you value reliable equipment, clear communication, and accountable planning, this is a platform to build a durable driving career.

Premium Equipment & Maintenance

A modernized fleet with proactive, scheduled maintenance to keep you moving safely and efficiently.

Strategic Dispatch & Planning

Intelligent routing and 24/7 cross-functional support designed to maximize your time, earnings, and work-life balance.

Driver Onboarding

SSP driver applications run through DriveDock, our digital onboarding platform. Start your profile, submit required details, and move through qualification steps in one secure workflow.

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Onboarding is open
Digital platform

Current Openings

Office and Operations Roles

Explore open positions across dispatch, planning, compliance, customer operations, and leadership support. Every role contributes directly to disciplined execution across the SSP network.

Total: 2
2 roles found
Tip: search by function, e.g. "dispatch"