Jen Vest’s energy and enthusiasm for life and real estate are contagious. As the co-founder of the Two Door Group at Compass, Jen has built a reputation for creating exceptional client experiences and fostering a team culture that thrives on collaboration and excellence. Her adventurous spirit and passion for entrepreneurialism have guided her path from the very beginning. 

“As a kid, my two favorite things were entertaining people and dreaming up business ideas. When I was about ten, I started producing this summer party and show where my friends and I would entertain our parents,” she recalls.

Jen attended Boston University, a move that cemented her future as a "city girl." During her time at BU, Jen studied abroad in London, and it had a profound impact on her. After graduating, she moved back to London to work full-time at the marketing agency where she had interned, but when her work visa was denied, she was forced to leave the UK. 

“I remember my manager asked me, ‘Where are you going to move to next?’ and I blurted out, ‘I guess New York.’ It was the first time I’d even thought about New York City!” Jen says, laughing.

She quickly found her footing in NYC, working for a boutique marketing and branding agency. She managed accounts for major brands, but her favorite projects helped launch entrepreneurial startup brands. “Those were the best [projects] because you really got to become part of the journey and build something together from the ground up,” she shares.

Jen's interest in real estate was sparked by a frustrating apartment hunting experience in Brooklyn in 2009. Taking charge of the search, she created detailed spreadsheets and relentlessly contacted listings, ultimately securing an incredible apartment despite minimal help from the landlord’s broker, who still charged a hefty fee. “I remember thinking, ‘Man, I could do this so much better,’” she recalls.

By 2013, Jen was ready for a change. A friend offered her a sublet in Chicago’s Hyde Park neighborhood, providing the perfect opportunity to explore a new city. Jen took it. She got a great job with a great marketing agency, but the grueling hours made her wonder about building a business in real estate.

Fate intervened in 2016 when that agency was acquired by another company. The disruption gave Jen all the push she needed. 

She began her real estate career as a solo agent at Baird & Warner in April 2017. It was there that she met Adele Lang. Jen and Adele quickly became friends, bonding over their shared love of travel, real estate, and business-building. As they got to know each other, a remarkable coincidence emerged: they discovered that they had both lived on Crondall Street, set within London's Islington neighborhood, at the same time in 2007, unknowingly residing just two doors apart. This serendipitous connection later inspired the name "Two Door Group," which symbolizes their unexpected meeting and the new opportunities they want to create for their clients.

Jen and Adele joined Compass and officially launched Two Door Group in 2018. Their goal was to build a client-focused real estate team that emphasized superior customer experiences and deep industry knowledge. Since then, the team has earned a reputation for its knowledge, resourcefulness, and genuine connections. They have grown in production and size annually and have been recognized with numerous awards and accolades. Jen has even hosted segments on episodes of Selling Chicago, a national TV show, on American Dream TV from 2022–2024.1 Today, the Two Door Group team consists of six agents and two support staff, as well as external partners. 

Jen and Adele continually obsess over refining their team’s systems and expanding their range of services, areas served, and languages spoken. “Our scale allows us to serve more client referrals,” Jen explains. “We’re helping our team agents reach new heights, we’re creating employment opportunities, and we’re building a team culture that we’re really proud of.”

Although Jen and Adele share a passion for construction and renovation, Jen shares, “What excites us most as team leads is the consistent, relentless pursuit of betterment.” Their core belief is that as entrepreneurs, they get to design and build the life they want, and they get to help their clients achieve their lifestyle dreams and financial goals in that same way.

In line with the intention of creating the life they want, Jen says, “We’re always looking to see how our professional goals fit into our personal goals and passions, versus taking what personal life is leftover after work demands. Happiness comes from challenging yourself, constantly learning, and being purposeful about what recharges and excites you.”

1  See clips at https://twodoorgroup.com/american-dream-tv/.