The Engineer Teaching AI to Run a Truck Dispatch

For most of its history, the American trucking industry has run on phone calls. A load needs moving, a broker picks up the line, a rate gets haggled over, and somewhere a dispatcher scribbles the details onto a whiteboard. It is a system that moves roughly seventy percent of the nation's freight, and until recently almost none of it was automated.

Aswin Chandrasekaran spent two years watching that reality up close before he decided to change it. As an engineering manager at TruckX, an Austin-based fleet technology company serving more than 100,000 commercial drivers, he saw how much of a small operator's week disappeared into repetitive back-office work. The trucks were connected. The paperwork was not.

“The driving was never the hard part,” Chandrasekaran said. “The hard part was everything that happened before and after the drive. Finding the load, arguing over the rate, sending the invoice. That is where independent truckers were losing hours every day, and it was work nobody had bothered to automate.”

Building Software That Does the Calling, Negotiating, & Paperwork

In May 2025 he co-founded Hey Bubba, known online as Bubba.ai, alongside TruckX founder Tapan Chaudhari and product lead Clarissa Luttmann. The company describes its product as a closed-loop autonomous dispatch system, one of the first of its kind for the trucking sector. Rather than showing a dispatcher a screen of recommended loads, the software is designed to act: it places outbound calls to brokers, negotiates rates, books freight, and handles the invoicing that follows. According to the company, more than 2,000 motor carrier fleets now use the platform, and its web properties draw upward of six million visits a week.

A Career Focused on Practical Problems

The path to that point runs through some of India's most competitive institutions and startups. Chandrasekaran studied at the Indian Institute of Technology Bombay, then founded his first company, Tessact, fresh out of school. That venture, an AI platform for video and audio analysis, won recognition at the AWS AI Conclave in 2017 for best media startup and was chosen by media conglomerate Viacom18 as one of five companies, from a field of more than 200 applicants, for a six-month co-innovation program. He later spent time in education technology, rebuilding payment and scheduling infrastructure for a learning platform used by millions, before moving into transportation with TruckX.

What connects those chapters, colleagues say, is a preference for the unglamorous problems. At Hey Bubba, the team chose to tackle broker negotiation first, arguably the messiest and most human part of the dispatch workflow, rather than starting with a simpler load-search tool.

“We started with the hardest problem on purpose,” Chandrasekaran said. “A load-search feature would have been easier to ship, but it would not have changed anyone's day. Automating the negotiation is where the value actually lives.”

Recognition and What Comes Next

That approach has not gone unnoticed in the broader engineering community. In 2026 Google named Chandrasekaran a Google Developer Expert in Cloud AI, an invitation-only designation the company reserves for experienced practitioners it considers influential in the field. He has also served as a judge at HackBLR, a Bangalore hackathon that drew more than 1,000 applicants, evaluating projects alongside engineers from Amazon and other Developer Experts.

Asked what he has learned from a decade spent building AI systems across three industries, Chandrasekaran keeps his answer plain. “The best AI product is the one that disappears into the workflow,” he said. “Truckers do not want a new app to learn. They want the paperwork to be done when they pull over. If the technology is doing its job, they should barely notice it is there.”

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