From Skepticism to Strategic: How AI Sales Conversations Are Evolving in Logistics

By Sean Chinski, Chief Sales Officer at Raft

A year ago, prospects would ask me: “Is AI just another buzzword?”


Last month, a CEO asked me: “Can we double our capacity without hiring?”

That’s the shift happening in logistics AI sales right now.

Not long ago, the reaction to AI in logistics was hesitation. Buyers wanted proof that it wasn’t hype. Today, boards are asking how fast they can scale it. The conversation has moved from if AI works to how it can transform the business.

What modern buyers want from AI in logistics

In every conversation, I hear the same priorities:

  • Proof and references: Buyers want peer validation, specific examples of how competitors have reduced costs, improved compliance, or increased revenue with AI.
  • Scalability: Pilots and small wins aren’t enough. Leaders want global AI programs that hold up in peak seasons when volumes surge and manual processes break down.
  • Integration: Most companies run multiple systems, including ERPs, TMS, and broker platforms. Buyers expect AI to serve as the connecting layer across these environments, augmenting existing systems rather than replacing them.
  • Consolidation: Many teams start with point solutions, an AI tool for customs, another for document processing, and a third for routing. Within months, they face vendor sprawl, overlapping features, and integration headaches. Buyers now want consolidation from the start.
  • ROI and trust: The bottom line is measurable outcomes. Buyers expect reduced costs, stronger compliance, and tangible ROI they can explain to leadership.

AI in logistics: From buzzwords to business outcomes

The language has changed. A year ago, I’d hear: “We want AI automation.”

Now the goals are precise:

  • Reduce tariff costs by 50%.
  • Improve accuracy in customs filings.
  • Increase throughput without adding headcount.

AI isn’t the headline anymore. Outcomes are.

From individuals to the boardroom

Decision-making has expanded. What once lived in operations or IT now sits in the boardroom. CFOs, COOs, and CEOs are directly involved, often with board-level oversight.

This executive involvement fundamentally changes the sales dynamic. It’s no longer enough to demonstrate features; you need to educate on strategic transformation.

How AI sales conversations differ from traditional software

Traditional logistics software sales are feature-driven. Buyers compare solutions, evaluate costs, and benchmark vendors.

With AI implementation, the questions run deeper:

  • Is the model accurate enough?
  • Will my team adopt it?
  • Can it integrate without disrupting workflows?
  • What best practices should we follow?

The result is more consultative sales. We’re now conducting multi-day workshops with 20, 50, or even 70 stakeholders, focusing not on product demos, but on sharing what AI is solving across the industry and discussing best practices. That’s how far the conversation has shifted.

What this means for logistics leaders

AI in logistics sales is no longer about overcoming skepticism. It’s about connecting proof, scale, and ROI to strategic priorities. Buyers want partners who can guide them through pilots, deliver quick wins, and scale globally.

The most successful AI partnerships in logistics don’t start with a demo; they start with a workshop. The companies winning today aren’t just vendors; they’re strategic partners guiding buyers from pilot to global scale, and that shift is reshaping the entire industry.

$1M annual savings & 2,000 extra hours a month await.

Explore how, on average, automating workflows for 3,000 shipments a month can lead to impressive annual savings. 
It all starts with a demo.