On Wednesday, September 23, CTO Insights officially arrived in Central Florida. We hosted our first Orlando event at OneRail’s headquarters, bringing together CTOs, VPs and directors of engineering, along with other technical leaders from across the region.
Our goal for this launch was simple: start building a strong, connected tech leadership community right here in Orlando. Judging by the conversations that filled the room, the demand is there.
The Talk: The Intelligence Behind the Last Mile
Last-mile delivery is one of the hardest problems in logistics. It involves unpredictable routes, tight delivery windows, and customers who expect real-time visibility. OneRail, an Orlando-based company, is tackling it with artificial intelligence, and its technology powers FedEx same-day delivery.
Two of OneRail’s technology leaders joined us for a moderated discussion:
- David Daeschler, Chief Data Science & AI Officer
- Chris Kucharski, Chief Technology Officer
They covered how OneRail uses AI to reshape last-mile logistics, what they’ve learned while scaling AI in production, and how they’re positioning their technology team for what comes next.
Key Takeaways from Kathryn Terry, a NextPath Recruiter Who Attended
- Candid, peer-to-peer conversations were the biggest value.
The format encouraged discussion rather than a formal presentation. It was more of a roundtable where technology leaders openly shared where their IT organizations started, how they got to where they are today, and what they’re working through now. - Leaders want practical answers from other leaders.
The conversation centered around real-world questions like: How did you handle this? What would you do differently? Did it actually work? Leaders were interested in lessons learned—not theoretical advice. - Peer-to-peer problem solving was a major theme.
Leaders were able to bring up challenges they’re facing and hear directly from others who had dealt with similar situations. Different experiences and approaches gave people ideas they could take back to their own organizations. - The smaller group made the conversations more valuable.
Because it was a smaller group, people had more opportunity to participate, ask follow-up questions, and go deeper into specific challenges rather than staying at a surface level. - There was a strong sense of “I’m not the only one dealing with this.”
One of the most valuable takeaways was hearing multiple technology executives say they were experiencing the same challenges. It created a sense of validation and helped leaders realize that many of the issues they’re navigating are broader industry challenges—not isolated problems within their own organizations. - The focus was on what is actually working.
Rather than simply discussing trends, leaders were able to compare what they had implemented, what worked, what didn’t, and what they would change if they could do it again.
Stephen Rideout’s Perspective
NextPath recruiter Stephen Rideout was struck by the scale of OneRail’s AI work. Chris and David shared examples of how the company has scaled AI to support FedEx same-day delivery and discussed how they’ve organized their AI team, including the cost savings their approach has created for OneRail.
For Stephen, the highlights were seeing AI applied at that level and hearing the open discussion it prompted among the leaders in the room.
More Than a Talk
The discussion was only part of the evening. CTO Insights is built around three things:
- Networking with fellow engineering leaders who face the same challenges you do
- Exclusive insights from executives operating at the forefront of enterprise tech
- Candid idea exchange, with open conversations about practical strategies for today’s biggest technical problems
Thank You, OneRail
A huge thank-you to OneRail for hosting our inaugural Orlando event and to David and Chris for sharing their experience so openly. We couldn’t have asked for better partners to launch with.
What’s Next
This was just the beginning. CTO Insights events are invite-only with limited seating, designed to keep conversations focused and valuable. If you’re a CTO, VP of Engineering, Head or Director of Engineering, or senior technical executive in Central Florida, we’d love to have you at the next one!
Be part of Central Florida’s technological transformation.
