Best Trucking Companies in Ontario, Canada
The 105 best Trucking companies in Ontario, Canada in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: WP Warehousing.
Our analysis of 50 Trucking companies
$4.1b in tracked funding; 71% of the stack-profiled cohort runs cloud-native; funding activity peaked in 2021.
Ranked: Best Trucking companies in Ontario
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Recent signals |
|---|---|---|---|---|---|---|---|---|
| 1 | WP Warehousing Provider of trucking, warehousing and logistics services 11Talent bottom 45%Global bottom 29%Funding bottom 24% All 3 signals ▾Talentbottom 45% Globalbottom 29% Fundingbottom 24% Talent: 1 named leader on record Global: Single-market focus (Canada) rank vs industry peers · Fliar Intelligence Index 11/100 | $30K | 119 mo ago | Seed | Dianne Todd Owner | 2009 | — | — |
| 2 | Ship With Pride Truckload Shipping | Freight Forwarding | PGL 48Innovation top 40%Product top 42%Funding top 44%Growth top 45% All 8 signals ▾Innovationtop 40% Producttop 42% Fundingtop 44% Growthtop 45% Marketbottom 44% Techbottom 38% Globalbottom 33% Newsbottom 21% Innovation: 2 product lines Product: 2 distinct product lines · Company stage: Conventional Debt rank vs industry peers · Fliar Intelligence Index 48/100 | — | 16 mo ago | Funding Raised | — | 2001 | PHPBootstrapApache HTTP Server+8 | — |
| 3 | Brimich Logistics Provider of temperature-controlled warehousing, logistics, and transportation services. 24Funding top 45%Talent bottom 49%Tech bottom 38%Market bottom 36% All 6 signals ▾Fundingtop 45% Talentbottom 49% Techbottom 38% Marketbottom 36% Growthbottom 35% Globalbottom 29% Funding: 1 rounds over 3 yrs (0.3/yr) · Last round PE (Sep 2023) Talent: 1 named leader on record · 1 C-suite/founder profile curated rank vs industry peers · Fliar Intelligence Index 24/100 | — | 33 mo ago | Late Stage | Tim Fergus CEO | 1997 | WordPressMySQLPHP+19 | 1 job opening |
| 4 | Livingston International Leading provider of global trade management, trade consulting, customs compliance, and freight solutions. 55Tech top 23%Product top 42%Market top 44%AI top 45% All 8 signals ▾Techtop 23% Producttop 42% Markettop 44% AItop 45% Growthbottom 46% Globalbottom 37% Newsbottom 21% Customersbottom 16% Tech: 39 technologies across 7/8 capability areas · Cloud: Amazon Alb, Amazon S3 Product: 1 published app (19.0k installs) · Company stage: Acquired rank vs industry peers · Fliar Intelligence Index 55/100 | — | 157 mo ago | Acquired | — | 1945 | WordPressSentryMySQL+21 | 1 job opening · 1 launch |
| 5 | Challenger Provider of transportation and logistics services 72Innovation top 20%Product top 26%Market top 42%Tech top 47% All 7 signals ▾Innovationtop 20% Producttop 26% Markettop 42% Techtop 47% Talentbottom 45% Globalbottom 36% Newsbottom 27% Innovation: 6 product lines Product: 6 distinct product lines · Company stage: Acquired rank vs industry peers · Fliar Intelligence Index 72/100 | — | 177 mo ago | Acquired | Dan Einwechter Owner | 1975 | WordPressApple iCloud MailMicrosoft 365+26 | 1 partnership |
| 6 | 301 Logistics Provider of truck & rail transportation, warehousing, and logistics services 19Talent bottom 45%Global bottom 25% All 2 signals ▾Talentbottom 45% Globalbottom 25% Talent: 1 named leader on record Global: Single-market focus (Canada) rank vs industry peers · Fliar Intelligence Index 19/100 | — | — | Unfunded | Ramon Carluen Owner | 1998 | — | — |
| 7 | Abramsautotransport Provider of automotive transportation services across North America 62Product top 24%Growth top 30%Innovation top 40%Tech bottom 49% All 6 signals ▾Producttop 24% Growthtop 30% Innovationtop 40% Techbottom 49% Talentbottom 45% Globalbottom 25% Product: 2 distinct product lines · Company stage: Public Growth: Web rank 50,000,000 → 10,000,000 YoY rank vs industry peers · Fliar Intelligence Index 62/100 | — | — | Public | Thomas Johnston Chief Executive Officer | 2016 | WordPressMySQLPHP+20 | 1 job opening |
| 8 | adlilogistics Provider of freight forwarding, warehousing, and distribution services | — | — | Unfunded | — | 1998 | Cart FunctionalityWordPressMySQL+8 | — |
Top 5 Trucking companies in Ontario
#1
Seed · St. Catharines, Ontario · founded 2009$30Kraised▾
Provider of trucking, warehousing and logistics services
- Jul 2016Seed$30K
#2
Funding Raised · Mississauga, Ontario · founded 2001 · 181 employees—raised▾
With more than 10 years of experience in the business and millions of shipments under its belt, Pride Group Logistics have all your shipping needs covered.
- Feb 2025Conventional Debt—
#3
Late Stage · Brantford, Ontario · founded 1997 · 121 employees—raised▾
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- Sep 2023PE—
#4
Acquired · Toronto, Ontario · founded 1945 · 1211 employees—raised▾
Livingston International is a leading provider of global trade management, trade consulting, customs compliance, and freight solutions. They offer customs brokerage services and trade consulting to help businesses navigate international trade regulations and ensure compliance. They also provide freight solutions for efficient and secure transportation of goods.
#5
Acquired · Cambridge, Ontario · founded 1975 · 2200 employees—raised▾
Provider of transportation and logistics services
Funding & investor landscape
Market landscape — 10 sub-themes by coverage
Share of Trucking coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising