Meet Jake Persofsky: Webinar Highlights
This week, we kicked off our new webinar series by introducing the freight world to a name you’re going to hear a lot more: Jake Persofsky, founder of Insperia and, as webinar host and industry influencer Trey Griggs put it, “freight’s most trusted IT guy.”
But this wasn’t your typical software demo or pitch deck parade. It was a conversation—part origin story, part IT therapy session—with a few Bruce Springsteen references sprinkled in. Here’s what we learned.
From Crashing Computers to Freight Crises
Jake’s tech journey started early—like, typing BASIC code from a magazine early. But it wasn’t just about loving computers. From the beginning, Jake was obsessed with solving problems.
That instinct eventually led him into IT roles across various industries, where he noticed a recurring pattern: when things broke, support was slow, impersonal, and way too generic. Especially in freight.
“People would call for help, and the support guy would ask if they’d restarted their computer,” Jake said. “Meanwhile, the TMS was down and loads were falling through the cracks.”
The Moment Insperia Was Born
Jake shared a key moment that changed everything. He was helping a hotel group stabilize their network when, after solving a massive tech issue, they told him:
“You’re not leaving. You’re staying. You get it.”
That idea—”you get it”—has become a core value at Insperia. Freight brokers and 3PLs don’t need someone to sell them software. They need someone who understands the way freight actually works.
Why Freight Brokers Deserve Better IT
Insperia exists because most IT providers still treat freight like any other industry. Jake’s team doesn’t.
They’re proactive. They speak the language. They know what happens when an EDI fails at 4:58 PM on a Friday.
And more importantly, they’re not just solving tickets—they’re building relationships.
“IT should be invisible when it’s working right,” Jake said. “It should never be the thing holding your ops team back.”
The Springsteen Side Hustle
Oh, and did we mention Jake plays keyboard and organ in a touring Bruce Springsteen tribute band?
Yes, really.
When he’s not helping freight teams recover from tech nightmares, Jake’s out on the road helping fans relive Born to Run. And somehow, those two worlds overlap more than you’d think.
“Whether I’m fixing a system or playing ‘Thunder Road,’ I want people to feel better when I’m done than when I started,” Jake said.
What’s Next
The next webinar in the Insperia series will feature Jake alongside a current client, digging into a real-world case study of how better IT support made a difference.
But for now, the message is simple:
Insperia is here to help freight teams finally get the IT support they deserve—responsive, knowledgeable, and freight-first.
Sign up now for the next webinar, Dissecting the 7 Most Common IT Challenges Freight Brokers Face, by clicking this link: https://streamyard.com/watch/jcDVfBe6ahGU.
