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.
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.
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.
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.
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.
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.
Shoaib Makani
Shoaib Makani is the co-founder and CEO of Motive (formerly KeepTruckin), an AI platform for the physical economy used by more than 120,000 fleets across trucking, construction, agriculture and field services. He left Khosla Ventures in 2013 to build software for an industry most of Silicon Valley ignored, and turned a paper-logbook replacement into a multi-billion-dollar company.
Justin Hall
Justin Hall is Co-Founder and Chief Commercial Officer of Augment, a San Francisco-based AI startup building 'Augie' — an AI teammate purpose-built for logistics operations. With 25 years spent founding, scaling, and selling logistics companies, Hall has held executive roles at YRC Worldwide (a $5B LTL carrier), PRIMO Logistics, and his own firm Logistics Planning Services before it was acquired by GlobalTranz. At Augment, he helped raise $110M in under six months — a $25M seed round in early 2025 and an $85M Series A in September 2025 — to automate complex freight workflows end-to-end. Outside of logistics, Hall founded Change Starts with Me, a nonprofit supporting BIPOC founders and underserved communities in the Twin Cities.
Rushil Goel
Rushil Goel is the CEO and Co-founder of Nirvana Insurance, an AI-native commercial trucking insurance company valued at $1.5 billion after a $100M Series D in December 2025. Before founding Nirvana, he spent five years at Samsara scaling fleet telematics from zero to $400M+ ARR, where he spotted the gap between how much safety data existed and how little insurance companies used it. An IIT Bombay CS grad with a Wharton MBA, Goel has built two companies and scaled products across India and the US - from mobile payments at Ola to connected fleet operations - before channeling everything into rebuilding commercial insurance from the ground up.
Tobenna Arodiogbu
Tobenna Arodiogbu is the co-founder and CEO of CloudTrucks, a San Francisco-based technology platform that gives independent truck drivers and owner-operators an all-in-one digital toolkit - from instant non-recourse payments and load booking to compliance management and business analytics. Born in Enugu, Nigeria, Arodiogbu previously co-founded Scotty Labs, an autonomous vehicle remote-operations startup that was acquired by DoorDash in 2019. CloudTrucks has raised over $141 million, including a $115 million Series B at an $850 million valuation led by Tiger Global and Menlo Ventures, making it one of the most well-funded platforms serving the backbone of American freight.
Julian Zheren Ma
Julian Zheren Ma is the founder and CEO of Inceptio Technology, the company behind what is arguably the world's most deployed autonomous trucking network. Based in Santa Clara and Shanghai, Inceptio has put over 4,000 Level 3 autonomous heavy-duty trucks on real freight routes, logging 500+ million commercial kilometers with zero fatal accidents. Before building Inceptio, Julian was a Corporate VP at Tencent overseeing LBS, search, and early autonomous driving initiatives, then president of G7, China's leading logistics big data firm. He holds a B.S. in Electrical Engineering from Shanghai Jiao Tong University and an MBA from IMD Switzerland, and is a Fellow of the Aspen Institute China Fellowship Program.
Sushanth Raman
Sushanth Raman is the co-founder and CEO of Pallet, a San Francisco-based AI company building an autonomous workforce for the logistics industry. Drawing on family roots in food distribution and stints at Microsoft, Google, and Retool, he founded Pallet in 2022 with fellow Retool engineer Andrew Spencer. The company has raised $50M total — including a $27M Series B led by General Catalyst in May 2025 — and its CoPallet platform automates the manual back-office operations (order entry, quoting, portal updates, shipment tracking) that still consume billions of dollars annually in a $12 trillion global logistics market.
Ted McKlveen
Ted McKlveen is the Co-Founder and CEO of Verne, a San Francisco-based clean energy company pioneering cryo-compressed hydrogen (CcH2) technology to decarbonize heavy-duty transportation and off-grid power. He graduated summa cum laude in Chemistry from Harvard and earned an MBA from Stanford GSB (2021), where he co-founded Verne. Under his leadership, Verne unveiled the world's first CcH2 Class 8 heavy-duty truck, secured backing from Amazon's Climate Pledge Fund and United Airlines Ventures, raised $15.5M total, and expanded into a new Pennsylvania manufacturing facility creating 61 jobs.
Harshita Arora
Harshita Arora is General Partner at Y Combinator - the youngest in the organization's history - having dropped out of school at 15 in Saharanpur, India, taught herself to code, built and sold a crypto app featured by Apple at age 16, won India's Pradhan Mantri Rashtriya Bal Shakti Puraskar, moved to San Francisco on an O-1 visa, co-founded AtoB (the 'Stripe for Trucking' valued at ~$800M), and was named to Forbes 30 Under 30 before joining YC as a Visiting Partner in 2025 and ascending to General Partner in April 2026 at age 25.