Kelley's an attorney and tax consultant at Flanagan Bilton, LLC, a law firm specializing in property taxes for commercial real estate. The company is based out of Chicago, and Kelley works there with five other Flanagans, including her father Thomas Flanagan, brothers Michael, John, and Thomas Jr., and sister Pamela. Thomas Sr. is the firm's managing partner, according to their website, while the siblings are all attorneys and tax consultants like Kelley.
Viewers don't have to wait until Hometowns to get to know Kelley's law-focused family (that is, if she makes it Hometowns). They were actually in her intro package in the first episode, long before viewers found out about her pre-Bachelor rendezvous with Peter Weber. In the short clip, Kelley said that she tries to separate her love life from her work and family life, in part because her "brothers are super overprotective." Indeed, one of them even said about Bachelor Peter Weber, "We've gotta ask him if he's joined the mile high club." Another lawyer at the table replied, "That's disgusting, he could be married to your sister," while Kelley looked away, seeming embarrassed but perhaps just playing along. That kind of joking around is an environment that working with your siblings and parents can foster.
Kelley didn't always work alongside her loved ones. According to Kelley's LinkedIn, before relocating to Chicago, she went to college at the University of Alabama for a degree in marketing. She even worked as a marketing manager for a dry cleaning company called DRYV for a couple of months before she went to law school. Kelley graduated in 2017 from the Chicago-Kent College of Law at the Illinois Institute of Technology. And in late 2018, she began working at her family's company where she resides today.
Kelley isn't the first attorney to take her shot at love on The Bachelor, with Bachelor contestants (and later Bachelorettes) like Andi Dorfman and Rachel Lindsay preceding her. And while many contestants (including Andi and Rachel) leave behind the jobs they came to the show with, Kelley is going strong at her company. It must help that her family runs the place and were cool about her taking a couple of months off to film the show.
Still, Kelley did worry about the effect the show might have on her career. During one of The Bachelor group dates, Kelley expressed concern that it may affect how her clients viewed her after the series. It was the pillow fight date where Kelley had to compete under the name "Kelley the Prosecutie" while in her underwear. She admitted to the cameras, "I'm a little nervous. I mean, who wants to see their attorney dressed in lingerie on a TV show?"
However, The Bachelor doesn't seem to have negatively impacted her career as of yet. Her "attorney" title is still listed first in her Instagram bio and she also posted a photo on Jan. 13 of her and her sister on the job in professional-looking blazers. "Work, work, work, work, work #sisters," she captioned the pic.
Besides, if any of the clients try to come for Kelley for being on TV, expect her brothers and the rest of her family to come to her defense. That's gotta be one of the perks of working with your family, at the very least.