Sightline 2027

One connected platform.
Run by AI.

Wednesday, September 16, 2026  ·  Loadsmart HQ, Chicago

19Days
:
14Hours
:
02Minutes
:
57Seconds

The Freight Platform That Runs Itself.

AI is changing freight faster than most people expected. And the most important thing that's changing isn't the software — it's what your team does all day.

Technology is moving fast. But the operations leaders getting ahead of it aren't the ones replacing their teams with algorithms. They're the ones figuring out which work belongs to the machine, and which work finally becomes worthy of their people.

That's what Sightline 2027 is about. Not the hype. The operational reality of where freight is heading and how to lead through it.

What to expect

AI in freight — the whole picture

Where agents already work, where they still fall short, and what the operation looks like when both are working together.

The role of the human team in an automated operation

A practical look at how the best transportation teams are repositioning, less execution, more judgment. And why that's a better job, not a smaller one.

Peer conversations with the people running it

Around 70 logistics and supply chain leaders from some of North America's largest shippers. Curated sessions and real time to talk through the challenges you're actually navigating.

Working sessions on your hardest problems

Dedicated time with product, engineering, and operations experts on the freight challenges that matter most to you. Not a Q&A panel. Actual working time.

September 16, 2026

Event Agenda

One day. One stage. A sightline into 2027 and beyond.

9:00 AMOPENING KEYNOTE

Software, AI, and Humans: The Freight Operation of 2030

Felipe Capella, CEO

9:40 AMPRODUCT

Six Agents, Zero Busywork: The Agentic Takeover of Freight Ops

Jill Prangnell, Senior Product Manager + Diogo Azedo, Senior Product Manager

10:10 AMPRODUCT

Beyond Visibility: Real Time AI Across Scheduling, Yard, and Dock

Aaron Thomas, Director of Engineering, Dock & Yard + Nate Allan, VP of Enterprise & Partnerships

11:00 AMWHAT COMES NEXT

Inside an AI-Run Freight Operation.

Derek Taliaferro, Director of Strategic Accounts + Michael Evans, Director of Strategic Accounts

11:45 AMEXTERNAL KEYNOTE

Who Builds the AI That Freight Won't?

1:10 PMCUSTOMER FIRESIDE

From Patchwork to Platform: Operators on Making the Shift

Enterprise Customer Speakers

1:50 PMLIVE REVEAL

One Connected Intelligence: Watch a Load Run Itself From Start to Finish

Paul Rehmet, VP of Product + Sam Belt, Director of Strategic Solutions

2:55 PMINTERACTIVE ROUNDTABLES

Your Freight. Your Questions.

3:40 PMCLOSING

The Day After: One Thing You're Going to Change

Felipe Capella, CEO

4:30–6:30 PMHAPPY HOUR

Happy Hour

Stick around for drinks and conversation with the rest of the room.

Limited Seats Available

Spots are reserved by invitation.

We're intentionally keeping Sightline a curated experience. If you're seeing this, it's because we believe your perspective belongs in the conversation.

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Loadsmart · Sightline 2027