Acting as the voice of reason when emotions run high, Dana Oliff steers clients towards success. As a realtor with the Olive Well Team at Compass, Oliff works with buyers and sellers throughout the city and northwest suburbs, collaborating with eight other agents, as well as a creative director, marketing director and operations assistant to provide every client with individualized attention and a seamless transaction. “In such a highly competitive industry, it is great to have teammates who collaborate without ego and truly want to help each other grow!” says Oliff, adding that together, they did over $50 million in volume in 2020 alone, earning the Gold award for volume from the Chicago Association of Realtors.

Born in Lombard and raised in DuPage County, Oliff moved to Chicago after graduating from the University of Illinois at Urbana-Champaign, first settling in Lincoln Park before moving in with her husband in Wicker Park. This year, she and her attorney husband, moved to a duplex in Ukranian Village/Humboldt Park and through visiting her in-laws on the North Shore, has become an expert in the Deerfield, Long Grove and Highland Park markets.

Joining the real estate industry five years ago after a career as an executive assistant at a Chicago-based law firm, Oliff found fulfillment from her new role, enjoying the opportunity to connect on a personal level with a diverse clientele and explore homes throughout the city. “I wanted something that inspired me more than a 9-5 desk job,” she explains. “I love that in real estate, no two days are the same and that I’m able to be a trusted resource within my network.”

Oliff loves entertaining and hosting and cites having a small dinner party as part of her ideal weekend. She’s an impassioned chef and enjoys experiment with new recipes.