trucking
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Chris Oliver Is Marketing to the Person Behind the Windshield
At Trucker Path, the chief marketing officer’s brief stretches from brand to product to truck parking. His method is simple enough to fit on a dashboard: ask drivers what gets in the way, then build around the answer.
Chris Silver Has Spent a Career Making Complicated Technology Feel Useful
From in-cab computers to fundraising software and back to the highway, the PrePass CMO has built a career around one stubborn question: does the technology make life clearer for the person using it?
Loki Cheema Learned Freight From the Hold Music
Before he built an AI operating system for trucking, Loki Cheema learned the business one favor, one form and one interminable phone call at a time. Hemut is his attempt to give freight back its hours.
The 30-Hour Spreadsheet That Built a Climate Startup
Trucking is the biggest carbon line item in almost every supply chain - and until recently, most carriers reported it by hand. Celine King built software to do it in seconds, and sold it to an industry that hates change.
The Startup That Read 400,000 Truck Crashes So Your Fleet Doesn't Become the Next One
Idelic turned a trucking company's in-house safety tool into a machine-learning platform that predicts crashes before they happen. In April 2026, Descartes bought it for up to $40 million.
The Chilean Freight Company That Hands Its Drivers the Keys to the Truck
RockTruck moved 1.7 million last-mile deliveries with a fleet it mostly does not own - then sold 70% of the company to a gas giant. Here is how the collaborative model actually works.
Coba
Coba is a cross-border financial infrastructure company built for businesses moving money between the United States and Mexico. It started in 2023 as a dual-currency consumer account for Latin American remote workers earning in dollars, and has since pivoted to B2B: multi-currency accounts, CLABE-enabled Mexican peso accounts for US companies, sub-24-hour carrier settlements, and embedded FX rails routed through banking partners, SPEI, ACH, SWIFT, wires, and stablecoins. Its sharpest focus is the US-Mexico freight and logistics corridor, where brokers and carriers have long been underserved by slow, opaque cross-border banking.
Terminal
Terminal is a universal API for telematics data in commercial trucking and fleet management. It connects to hundreds of telematics service providers - GPS, safety events, fault codes, dash-cam media, driver hours - and delivers that data in one normalized feed, so insurers, fleet software, logistics firms and fintechs can build products without wiring up hundreds of one-off integrations. Often called 'the Plaid of trucking,' the Toronto company was founded in 2023, went through Y Combinator's S23 batch, and has raised $26M to date.
Harish Abbott: Building the AI Teammate Rewiring Global Logistics
On Joe Lonsdale's American Optimist podcast, serial entrepreneur and billionaire Harish Abbott, co-founder and CEO of Augment, explains how his AI teammate 'Auggie' is transforming the fragmented $10 trillion global logistics industry. Abbott, who previously built Deliverr (sold to Shopify for roughly $2.1 billion) and helped build Amazon's fulfillment network, argues that AI's reasoning models and expanding context windows finally make it possible to automate the endless emails, phone calls, and texts that move freight. Auggie already helps manage roughly $25 billion in freight, works 24/7 across email, phone, Telegram and WhatsApp, and follows written workflows like a human employee. Abbott lays out a massive opportunity: not just tens of billions in productivity gains, but a $300 billion U.S. (nearly $1 trillion global) chance to cut waste from an industry hobbled by low-bandwidth, asynchronous communication.
Highway
Highway is a Dallas-based logistics technology company that built the freight industry's Carrier Identity platform, verifying that the carrier a broker books is who they claim to be. Founded in 2022 by former TriumphPay CEO Jordan Graft, Highway connects a carrier's digital identity to its physical operations to stop double brokering, impersonation and freight fraud in real time. Its Identify, Connect and Monitor products - plus the newer Trusted Freight Exchange - serve more than 1,050 brokers, including 70 of the 100 largest freight brokers in the United States.
Deepak Chhugani
Deepak Chhugani is the founder and CEO of Nuvocargo, an AI-powered platform for cross-border truckload freight between the United States and Mexico. Born in Kenya to Indian parents and raised in Ecuador, he worked on Latin America M&A deals at Bank of America Merrill Lynch before starting Nuvocargo in 2019. The company has raised more than $75 million from investors including Y Combinator, Tiger Global, QED, and NFX, and combines freight forwarding, customs brokerage, cargo insurance, and financing on one platform. Chhugani was named to the Forbes 30 Under 30 list for enterprise technology in 2023 and is an Endeavor Entrepreneur.
Nuvocargo
Nuvocargo is a digital-first freight forwarder and licensed U.S. customs broker built to simplify the $40B+ over-the-road freight market between the United States and Mexico. Through a single platform, it combines trucking, customs clearance, cargo insurance, carrier payments and trade finance, and is increasingly layering AI automation across the load lifecycle. Founded in 2019 by Deepak Chhugani, the New York- and Mexico City-based company has raised over $74M and rode the nearshoring wave to serve roughly 500 shippers including Kimberly-Clark, Nestle and Grupo Bimbo.
Jordan Graft
Jordan Graft is the founder and CEO of Highway, a Dallas-based freight technology company he started in 2022 to solve carrier identity and fraud in trucking. A three-time CEO before 40, he previously led TriumphPay to become the largest payer of freight invoices in the US, co-founded the software shop CrateBind, and worked in private equity at TA Associates and investment banking at J.P. Morgan. Highway coined the category of Carrier Identity and now partners with the largest US freight brokerage, C.H. Robinson.
Michael Mecca
Michael Mecca is the founder and CEO of PortPro, a Kearny, New Jersey based software company building a TMS purpose-built for drayage carriers and brokers. He grew up in his family's intermodal trucking business, Mecca & Son Trucking, then co-founded Axle Technologies before launching PortPro in 2019. Under his leadership PortPro raised a $12M Series A in 2023 and now serves 550+ drayage companies, layering AI agents (Jerry, Helen) on top of its operating platform.
BlueCargo
BlueCargo is a logistics SaaS company that helps importers, freight forwarders, and drayage carriers monitor, forecast, and dispute the accessorial fees - demurrage, detention, and per diem - that pile up when shipping containers get stuck moving from port terminals to their first warehouse. Founded in 2018 by French engineers Alexandra Griffon and Laura Theveniau after they met near the Port of Oakland, the company aggregates data from North America's busiest container ports and uses AI to audit freight invoices and reclaim overcharges, having saved customers more than $175M in fees.
Drōv Technologies
Drōv Technologies is an Oklahoma City company building smart-trailer technology for the trucking industry. Its flagship AirBoxOne platform unifies tire inflation, wheel-end, load, temperature, door, and impact sensors into a single connected system that streams real-time diagnostics to drivers and fleet offices. Founded on a legacy of tire-inflation hardware expertise, Drōv aims to make trailers as connected as the tractors pulling them, targeting fuel efficiency, uptime, safety, and predictive maintenance across dry vans, reefers, and petroleum tankers.
Vendorflow
Vendorflow is a Los Angeles-based unified communications platform for trucking fleets, freight brokers, ports, and terminals. It consolidates voice, SMS, WhatsApp, and ELD in-cab messaging into a single shared inbox that integrates with TMS and ELD systems, so dispatch and operations teams can collaborate on driver conversations in one place - no app installs required for drivers.
Guillermo Garcia
Guillermo Garcia is the co-founder and CEO of SmartHop, a Miami-based platform that acts as an autonomous dispatcher and 'business-in-a-box' for small trucking companies and owner-operators. A Venezuelan industrial engineer who started out delivering pet food, he built a bootstrapped ~500-employee logistics company back home before political and economic instability pushed him to the U.S. After studying at Columbia and running an over-the-road fleet in Miami, he founded SmartHop in 2017-2018 to give independent truckers the software, load recommendations, and financial tools that big carriers take for granted. SmartHop has raised over $56M, including a $30M+ Series B in 2022.
Jin Stedge
Jin Stedge is the co-founder and CEO of TrueNorth, a San Francisco freight-tech company building an AI loadboard and virtual dispatcher named Loadie that helps independent truckers find loads, price them, and get paid. Born in Korea and adopted at seven into an American family of owner-operators, she studied aerospace engineering at MIT, did neuroscience research, and worked in HR tech and autonomous driving before returning to her family's roots in trucking. She founded TrueNorth in 2019 with Sanjaya Wijeratne, raised a $50M Series B backed by Sam Altman and Lachy Groom, and earned a spot on Forbes 30 Under 30.
Terraline
Terraline is a Bay Area vehicle technology company founded in 2021 (originally Solo Advanced Vehicle Technologies) by ex-Tesla and Waymo engineer Graham Doorley. It set out to decarbonize freight with a clean-sheet, battery-electric Class 8 long-haul truck, the Tangra LH1, boasting 500+ miles of range and the lowest drag coefficient of any Class 8 truck. The company has since evolved toward a software-defined vehicle (SDV) platform - a central compute system, cloud telemetry, and an AI backend - aimed at modernizing the electronic architecture of heavy machines.
Cargomatic
Cargomatic is a digital freight marketplace and technology platform that connects shippers with local and regional trucking capacity in real time. Founded in 2013 and headquartered in Long Beach, California, it specializes in drayage and short-haul freight - moving containers off ports and onto roads - alongside intermodal, full-truckload (FTL), less-than-truckload (LTL), and white-glove delivery. By pairing a carrier mobile app with smart routing and bundling software, Cargomatic helps fill empty truck miles, speed cargo off congested docks, and give shippers visibility into shipments that traditionally lived on paper and phone calls.
FleetWorks
FleetWorks is a San Francisco AI company rebuilding how freight gets matched and booked. Its voice and text AI agents handle the phone calls, texts, and emails that brokers and carriers trade to cover loads - work that has barely changed since the 1980s. Launched out of Y Combinator in 2023 by ex-Uber Freight and ex-Airbnb operators, FleetWorks now runs an 'always-on dispatcher' that connects with thousands of carriers daily and works with over 40 U.S. brokerages, including 15 of the top 100.
Marc Khoury
Marc Khoury is the co-founder and CEO of aifleet, an Austin-based tech-native trucking company that uses proprietary AI to schedule routes, automate load booking, and keep its employee drivers busier and better paid. A civil engineer turned management consultant, he ran strategy at US Xpress before launching aifleet in 2020 to attack what he calls trucking's real problem: not a driver shortage, but a retention problem rooted in an inefficient, fragmented $400 billion market. The company has raised roughly $55 million and grown its fleet from dozens of drivers to hundreds.
Shipwell
Shipwell is an Austin-based software company building an AI-integrated transportation management system (TMS) that unifies shipment planning, real-time visibility, automation, and settlement in one cloud platform. Founded in 2016 by Greg Price and Jason Traff, it helps shippers and logistics teams across food & beverage, manufacturing, and distribution move freight with less manual work. After selling its brokerage arm to CloudTrucks in 2024, Shipwell now operates as a pure-play SaaS provider and has been named a Visionary in the Gartner Magic Quadrant for TMS for five consecutive years.
SmartHop
SmartHop is a Miami-based trucking technology company that gives small fleets and owner-operators a business-in-a-box platform. It pairs AI-driven load recommendations and full-service dispatch with fintech tools - fuel cards, payments, and insurance - so independent truckers can compete with large carriers without drowning in paperwork.
TrueNorth
TrueNorth is a San Francisco software company building the operating system for trucking. Its AI dispatcher, Loadie, pulls freight from across the market and books loads for independent carriers and brokers - matching trucks to the most profitable freight, automating paperwork, and handling outreach. Backed by Sam Altman and Lachy Groom, the company wants to give solo truckers the economics and tooling of a large fleet.
Paul Singer
Paul Singer is the cofounder and CEO of FleetWorks, a San Francisco startup building always-on voice AI agents that handle the phone-and-email grind of freight brokerage. A former Uber Freight product manager and Yale economics grad, he started FleetWorks in late 2022 with cofounder Quang Tran, went through Y Combinator's Summer 2023 batch, and in October 2025 raised a $17M round (including a $15M Series A led by First Round Capital) to automate the matching of trucks with cargo across a $1T+ industry.
Richard Gerstein
Richard Gerstein is the Chairman and CEO of Cargomatic, the marketplace that matches local and regional freight with the trucks already driving past it. He grew up on the docks of his father's less-than-truckload business in Chicago, founded the multi-modal logistics software company IntelliTrans, and since 2017 has rebuilt Cargomatic into a leading provider of local LTL, drayage, and white glove freight services. He pairs a UC Berkeley transportation engineering background with a lifetime spent around loading docks.
RoadFlex
RoadFlex is a modern Visa fuel and expense card platform built for growing fleets. It gives fleet operators real-time visibility and control over fuel and work-related spending, layering AI-driven fraud detection, telematics-based purchase validation, automated reconciliation, and IFTA fuel-tax reporting on top of a card accepted at virtually every fuel station. The company positions itself as the transparent, software-first alternative to legacy fuel-card incumbents like WEX and Corpay (Fleetcor).
Motive
Motive (formerly KeepTruckin) is a San Francisco-based technology company building an AI-powered platform for the physical economy. It helps companies that run trucks, equipment, and field workers manage safety, operations, compliance, and spend in one system - combining edge-AI dashcams, GPS telematics, and fintech tools used by nearly 100,000 businesses from small fleets to Fortune 500 enterprises like Halliburton, Komatsu, and Maersk.