---
title: "Sightline 2027 Session Recaps: All 7 Sessions | Loadsmart"
description: Every Sightline 2027 session for Enterprise Shippers in one place, from the 2030 keynote to the live AI agent call.
image: https://blog.loadsmart.com/hubfs/sightline-2027-session-recaps-cover-1140x720.png
---

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# Sightline 2027: Every Session Recap in One Place

 by [**Sarah Fidrych**](https://blog.loadsmart.com/author/sarah-fidrych)

**Key Takeaways**

- Sightline 2027 brought Enterprise Shippers to Chicago for seven sessions.
- Speakers covered AI agents, the dock and yard, and two customer stories.
- Each session has its own recap on our blog with the full recording.
- Start with the session closest to the workflow your team wants to change.

Sightline 2027, our first annual event for Enterprise Shippers, took place at our Chicago headquarters on September 16th, 2026. Across seven sessions, Loadsmart leaders, customers, and a Journal of Commerce editor talked about how AI is changing the way freight gets run, and what [Loadsmart AI](https://loadsmart.com/ai/) looks like on a real load.

This post puts all seven in one place, in the order they happened on the day, so you can jump to the one that fits where your team is with AI. For a look at the day itself, read [Inside Sightline 2027: Our First Annual Event for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-for-enterprise-shippers).

## **Every Sightline 2027 Session in One Place**

### Session 1: The Freight Operation of 2030

Felipe Capella, CEO and Co-founder of Loadsmart, opened the day with his view that software, AI, and freight experts each own a different part of the work, and what that means for a freight operation in 2030.

Read the recap: [Sightline 2027: The Freight Operation of 2030 for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-freight-operation-of-2030).

### Session 2: Six Agents, Zero Busywork

Jill Prangnell and Diogo Azedo, Senior Product Managers at Loadsmart, explained what each of the six Loadsmart AI agents does and where its work ends and your team's begins.

Read the recap: [Sightline 2027: Six Agents, Zero Busywork](https://blog.loadsmart.com/sightline-2027-six-ai-agents).

### Session 3: Beyond Visibility

Aaron Thomas, Director of Engineering, Dock and Yard, and Nate Allan, VP of Enterprise and Partnerships, showed how Opendock is adding AI to dock scheduling and yard management, including MCP (Model Context Protocol) servers that let AI tools work directly with your dock data.

Read the recap: [Sightline 2027: AI Across the Dock and Yard for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-ai-dock-and-yard).

### Session 4: Inside an AI-Run Freight Operation

Derek Taliaferro and Michael Evans, Directors of Strategic Accounts at Loadsmart, talked about what AI freight operations mean for the people doing the work.

Read the recap: [Sightline 2027: AI Freight Operations for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-ai-freight-operations).

### Session 5: Who Builds the AI That Freight Won't?

Eric Johnson, Senior Editor of Technology at the Journal of Commerce, covered why AI in logistics stalls and where Enterprise Shippers can start.

Read the recap: [Sightline 2027: Who Builds the AI That Freight Won't?](https://blog.loadsmart.com/sightline-2027-who-builds-freight-ai)

### Session 6: From Patchwork to Platform

Felipe moderated our customer panel, where Babylist and Scotts Miracle-Gro shared how they moved their logistics operations off spreadsheets and email. On the panel:

- Joe Deveney, Director of Transportation Logistics, Babylist
- Brendan Donovan, Transportation Manager, Babylist
- Sean Ryan, Distribution Operations Manager, Scotts Miracle-Gro
- Nick Prusakiewicz, Director of Contract Manufacturing and Distribution, Scotts Miracle-Gro

Read the recap: [Sightline 2027: From Patchwork to Platform for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-logistics-operations-panel).

### Session 7: One Connected Intelligence

Paul Rehmet, VP of Product, and Sam Belt, Director of Strategic Solutions, followed one load from order to payment through Loadsmart AI, then Sam called an AI agent live as a carrier who needed to move an appointment.

Read the recap: [Sightline 2027: One Connected Intelligence for Enterprise Shippers](https://blog.loadsmart.com/sightline-2027-one-connected-intelligence).

## **Where Should Enterprise Shippers Go Next?**

Every session is also on the [Sightline 2027 hub](https://sightline.loadsmart.com/), where you can request downloadable versions to share with your team.

Loadsmart is offering three ways to see Loadsmart AI in action on your freight first:

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

AI runs your freight, and our experts handle the exceptions.

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## **Frequently Asked Questions**

### What was Sightline 2027?

**Sightline 2027 was Loadsmart's first annual event for Enterprise Shippers, held at our Chicago headquarters on September 16th, 2026.** It had seven sessions on how AI is changing freight operations, from a keynote on the freight operation of 2030 to a live call with an AI agent.

### Where can I watch the Sightline 2027 sessions?

**Each session recording is embedded in its recap post on the Loadsmart blog and on the Sightline 2027 hub.** On the hub, you can also request downloadable versions to share with your team.

### How can Enterprise Shippers see Loadsmart AI on their own freight?

**Loadsmart offers three ways to see Loadsmart AI in action on your freight first.** You can request a personalized demo on your highest-impact workflow, a one-day onsite workshop, or a proof of concept on your data.

Topics: [Loadsmart AI](https://blog.loadsmart.com/tag/loadsmart-ai)

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  "dateModified" : "2026-11-12T18:00:20.367Z",
  "datePublished" : "2026-11-12T18:00:20.000Z",
  "headline" : "Sightline 2027 Session Recaps: All 7 Sessions | Loadsmart",
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