Jessi Underhill

Licensed Real Estate Broker
License No: 475.192075
(773) 840-8425

I can help you with:

Farm Real Estate

Farm Finance

Farm Management


Jessi Underhill joined Tillable in June 2019 as manager of customer experience. In that position, she works with both farmers and landowners to make sure they understand the platform and to answer any questions they may have. She also keeps landowners up to date on the status of their land and farmers up to date on the status of their pending offers or current contracts.

Jessi grew up on a farm in southeast Iowa (Davis County), where her grandmother still owns and rents out farmland. She and her family moved to the south suburbs of Chicago when Jessi was entering high school.

A former public school teacher for eight years (high school social science), Jessi has a master’s degree in training and development and is a veteran of several small startups in the Chicago area. That background serves her well every day as she interfaces with farmers and landowners, which she says is most frequently by telephone or via the website chat function.

At the end of my final interview, I really showed all my cards. I said, “This is where I want to be. This is a product I want to be a part of, and a team I want to be a part of.” I just laid it all out: “This is what I want to do.”

“Our farmers especially want to talk to somebody,” Jessi says. “They want that personal interaction. The landowners are more likely to communicate by email, but our farmers want to actually speak to someone. They want to know that they’re working with a human and not just a machine.” And that’s where Jessi and the rest of the customer experience team come in.

What’s Jessi’s favorite thing about Tillable? “The people are fantastic,” she says. “They’re incredibly intelligent and hardworking. Everybody has the same end goal in mind, and they are really working together to reach that goal of growing the company and providing this fantastic product to both landowners and farmers. This is what really drew me to Tillable and it’s also my favorite part.”