Callie Simon has a knack for building relationships and thrives on connection. With a natural ability to bring people together and a drive to lead, she turned an uncertain start in real estate into a remarkable career—becoming one of the youngest managing brokers in Chicago and inspiring others to dream big.

Callie’s love for people and connection has always been a defining trait. As a child, her social nature often stood out. “People used to call me the bag lady,” she laughs. “I’d collect toys on the playground and when anyone wanted them back, they’d have to talk to me, and that allowed me to get to know them a bit.”

That early instinct for interaction and negotiation hinted at her future in real estate, where conversations and relationships are at the heart of her work. “I thrive on conversations and getting to know others,” she emphasizes. “I've been called a collector of personalities and friends from all walks of life.”

Originally from New Hampshire, Callie grew up surrounded by mountains, lakes, and Boston’s city life. Her family—including her parents and younger brother, Connor, who today is a standout hockey player—instilled in her a strong work ethic and appreciation for community. In 2010, she moved to Chicago, ready for new opportunities and challenges.

After graduating from Columbia College Chicago in 2014 with a degree in marketing and advertising with a focus in graphic design, Callie faced the same uncertainty many college grads experience. “Finding a good design job was tough,” she recalls. “I didn’t have much experience, so like most twenty-one-year-olds, I turned to Craigslist.” That’s where she found an admin job at a small real estate brokerage—an opportunity that changed everything.

Callie started on the operations side of the business, but it didn’t take long for her to realize she wanted more. Drawn to the management and leadership aspects of the industry, she set her sights on becoming the youngest managing broker at Compass. “I wanted to be involved in the deals and support agents through every phase of their growth,” she says. “I wasn’t just thinking about my own career. I was already thinking about how I could help others.”

Callie joined Compass in its early days in the Midwest and quickly rose through the ranks. She wore multiple hats—operations, growth, and recruiting—before landing her current role as sales manager for Compass’s Lincoln Park office. She now helps agents build their businesses and navigate challenges with confidence.

“I’m passionate about connecting with my agents both professionally and personally,” she shares. “Whether it’s helping them reach production goals, take time off, or tackle tough negotiations, I’m in their corner every step of the way.”

Callie’s management style is deeply rooted in empathy and collaboration. “Helping everyone find their place in this world might sound cliché,” she admits, “but it’s truly what drives me. The support and passion we put into our work as a team helps our agents provide the same to their clients.”

Callie credits much of her growth to the mentors who’ve guided her along the way. Industry leaders like Fran Broude and Joe Siciliano have not only shaped her approach, but also fueled her drive to keep evolving.

Looking ahead, she plans to double down on her current role. “I would love to still be managing the number one office in Cook County and Chicagoland alongside my two best mentors, Joe Siciliano and Fran Broude,” she says.

Despite her rapid rise, Callie is quick to point out that success is about more than titles, numbers, or one-time achievements. “The biggest part of success, I believe, is happiness and longevity,” she shares. “My husband once told me that he was proud of me for finding a career that truly fulfills me. I feel that too.”

Outside of work, Callie embraces balance. Her ideal Saturday morning involves a slow start in Old Town, having coffee and breakfast at Kanela Breakfast Club, and spending time with her best friend and husband, Mike Flashenberg. Callie recently started playing golf and can already tell it’s going to be her new obsession.

Whether she’s helping agents hit their goals or working on her swing, Callie’s persistence, passion, and knack for connection will continue to take her to new heights. Having already become one of the youngest managing brokers in Chicago, her story is still unfolding, and she’s just getting warmed up.