The AI Tax on Brokerages, and What It Means

Content for this blog came from the recent TIA Livestream, The AI Tax on Relationships: Automating Brokerage Without Losing Your Edge

What to Know: Artificial intelligence is reshaping freight brokerage, but the threat isn’t robots taking jobs. It’s competitors who know how to use the tools and do.

That’s the central argument Dhruv Gupta, CEO and co-founder of Drumkit, made on a recent TIA Livestream focused on automating freight brokerage without losing the relationship edge that defines the business.

The “AI tax” on relationships: Gupta opened with a warning he doesn’t take lightly, even as someone building an AI company. Automate the wrong things, he argues, and you quietly erode the trust that makes shippers choose you over a cheaper alternative.

“It’s very common for shippers to accept a higher rate because they trust your service,” Gupta said. The moment automation makes a customer feel shortchanged, that premium evaporates.

His rule of thumb: automate actions, not decisions.

What that looks like in practice:

• Automate it: Load building, spot quoting, order entry, inbound carrier calls for basic information, scheduling and tracking updates
• Keep humans in it: Customer acquisition conversations, carrier relationship management during exceptions, anything where personality and judgment determine the outcome

“Phone calls in particular are places where someone’s calling you because they want to talk to a person,” Gupta noted. Even when AI handles routine inquiries, brokers should make clear there’s a human available, because trust gets built with people, not software.

Where the real competitive advantage lives: As more brokers access similar technology, Gupta argues the differentiator won’t be the tools — it’ll be the person behind them.

Quoting speed, automated load building, and AI-assisted outreach are becoming table stakes. What isn’t commoditized is the broker who shippers genuinely want to work with. “90% of the time, people choose you because they like you,” he said.

The brokers who win will be the ones who use AI to get out of the weeds, and spend that recaptured time doubling down on the relationships no algorithm can replicate.

The bottom line: Don’t buy AI because it sounds impressive. Start with your biggest bottlenecks, spot quoting and order entry top Gupta’s list, build clear benchmarks, and protect the parts of your business where your personality is the product.