Inside Sightline 2027: Our First Annual Event for Enterprise Shippers

Key Takeaways

• Our first Sightline brought 28 companies to our Chicago Headquarters.
• We rolled out Loadsmart AI and six AI agents for Enterprise Shippers.
• The day closed with an AI agent making a live phone call on stage.
• Every session from the day is being released in full over the coming weeks.

On September 16th, we opened our Chicago headquarters for the first-ever Sightline: a full day for Enterprise Shippers on what AI can actually change inside a freight and logistics operation.

We introduced Loadsmart AI and the six AI agents that come with it. Seven sessions took place with a single theme running through it all: getting the balance right between people, technology, and AI.

We welcomed 28 companies alongside our own freight experts and the product and engineering teams behind Loadsmart AI. Customers took the stage and shared with their peers their logistics challenges and lessons. Eric Johnson, Senior Editor of Technology, Journal of Commerce, told the room they are not as far behind as they think in AI adoption. And to wrap the day, an AI agent took a live phone call on stage.

This was our first Sightline, and we left inspired by what we can build together. Here is how the day went, with every session being released in full over the coming weeks so you can hear it from the people who were in the room.

Why Did We Create Sightline?

The day was built around one question: how do people, technology and AI fit together in a freight operation, and who decides what?

The future of freight should not be built in isolation. It should be built with the people who will have to run it. Sightline was created to bring them into one room: enterprise shippers, freight experts and industry leaders. The day was filled with real conversations about where the industry is going.

Who Did We Welcome to Chicago?

Loadsmart's headquarters welcomed enterprise shippers from 28 companies and as far away as Colombia, for a full day of collaboration and conversation.

They sat alongside our own freight experts and the engineers and product managers who built Loadsmart AI. Every question about how the technology behaves in a real operation had someone in the room who could answer it properly.

The people who run freight every day spent the day with the people who built the software, which is exactly what we hoped for.

What Did We Share With Enterprise Shippers?

Loadsmart AI and its six AI agents were the core of what we shared with Enterprise Shippers at Sightline 2027. Each one takes on repetitive work our customers know well, from filing documents to rebooking an appointment after a pickup slips.

• Document collection and filing. Captures rate confirmations, BOLs, PODs and invoices as they arrive, classifies them, and files them against the right shipment.
• Tracking and status updates. Pulls carrier status on a schedule, chases the carriers that go quiet, and pushes clean updates to your team and your customers.
• Tender failures and retendering. Retenders down your routing guide when a carrier rejects or times out, inside a cost ceiling that keeps the fallback from costing more than the miss.
• Proactive load audits. Checks loads before pickup, flags at-risk transit while it can still be fixed, and audits charges before they are paid.
• Claims processing. Gathers the documentation, validates the claim against the shipment record, and drafts the filing for your approval.
• Scheduling and rescheduling. Books dock appointments against the facility's live availability, then detects a slipped pickup, rebooks it, and notifies relevant contacts.

If your operation runs a repetitive workflow outside those six, our team can scope the build of an AI agent for it.

People should keep the judgment, the relationships, and the decisions. When an AI agent cannot finish something, it should not land back on your desk. That is where our own freight experts step in to finish the task.

AI runs your freight. Our experts handle the exceptions.

What Defined the Day?

The day was defined by the people in the room and the conversations had by customers and their peers.

Felipe Capella, Loadsmart's Co-founder and Chief Executive Officer, opened the day on the split between what the AI agents take and what people keep. Jill Prangnell and Diogo Azedo, both Senior Product Managers for ShipperGuide, then walked through the six agents one at a time.

Aaron Thomas, Director of Engineering for Opendock, and Nate Allan, VP, Enterprise & Partnerships, took the same idea into dock and yard with the next layer: AI that connects visibility to real time action. Derek Taliaferro and Michael Evans, both Directors of Strategic Accounts, focused on three questions: what should your team still own, what should technology execute, and where do your people create the most value.

Felipe sat down with customers from Babylist and Scotts Miracle-Gro: Joe Deveney, Director of Transportation Logistics, and Brendan Donovan, Transportation Manager, from Babylist, and Sean Ryan, Distribution Operations Manager, and Nick Prusakiewicz, Director of Contract Manufacturing and Distribution, from Scotts Miracle-Gro. They walked through their freight operations, including internal processes and what they would do differently if they were starting over.

Eric Johnson, Senior Editor for Technology at the Journal of Commerce, gave the keynote and said that nobody is as far behind on AI as they feel. Most companies have started in some way, and in his view the time it takes to catch up is shrinking rather than growing.

Paul Rehmet, Vice President of Product Management, and Sam Belt, Director of Strategic Solutions, closed the day by putting an AI agent on a live phone call in front of the room rather than talking about what it could do.

People asked questions about their own facilities, data, and teams, and kept the conversation going long after the sessions ended during happy hour.

Where to Go From Here?

Felipe made the offer to everyone in the room, and it is open to anyone reading today. All three are available before any contract starts:

• A personalized demo built on your highest-impact workflow, running on your own freight
• A one-day onsite workshop, where we come to you
• A proof of concept working on your data

Start with one workflow and one conversation. That is how every one of these begins.

Thank you to everyone who came to Chicago and made the first Sightline what it was. We are already planning Sightline 2028, and we are building it around what we heard this time.

Frequently Asked Questions

What was Sightline 2027?

Sightline 2027 was Loadsmart's first annual customer event, held September 16th, 2026 at our Chicago headquarters. Seven sessions covered Loadsmart AI and its six AI agents, a live agent demo, and a customer panel with Babylist and Scotts Miracle-Gro.

Where can I watch the Sightline 2027 sessions?

Every session will be published in full on the Sightline hub (to be released), alongside the decks and the photos from the day. Downloadable versions are available on request for sharing within your own company.

Will there be a Sightline 2028?

Yes! Planning is already underway. You can join the waitlist on the Sightline hub to be invited when registration opens.