| Love of learning paves path to COO
With 18 years in the industry including as a real estate attorney on the buy, sell and contractual side of transactions, as an underwriter and in title operations, Kathy Kwak imagined she might be named chief operating officer of a title company “someday.” That day came much sooner than she anticipated.
 Kathy joined Chicago-based Proper Title, LLC, in 2017, rising from director of title to vice president to executive vice president to COO. The company flourished under her guidance, including a record-setting 2021 where residential closings were up 41 percent over 2020 and commercial closings were up 121 percent.
How did she accomplish so much in such a short amount of time?
“I asked a lot of questions,” she says. “I was fascinated with improving processes and workflows.”
She enjoyed learning about all the different parts of the title process. Before long Proper Title’s interim CEO promoted her to executive vice president. The decision came near the start of the pandemic, when “the world turned upside down,” Kathy says.
“She called me and said, ‘We need for you to step in, and I’ll be here with you along the way. You’re someone that’s very capable, you understand the title process, you work very well with the staff. Let’s go with it,’” she says.
During that time, Kathy spearheaded remote and curbside closings to guide Proper Title through the pandemic shutdowns without canceling a single closing. As a result, she was promoted to her current role as COO less than a year after being named EVP.
“It’s been quite an adventure,” she says. “I honestly did not think becoming COO would happen so fast. I thought maybe when I’m 50, I can start thinking about how to get there. COVID taught me that anything unexpected can happen.”
Kathy’s path to COO had some twists and turns. After earning her law degree, Kwak was in-house counsel for a Chicago-area relocation company, where she learned a lot about residential real estate quickly.
She next worked as an associate at a firm focused on special needs trusts. Following the 2008 housing market crash, Kathy worked long hours negotiating short sales with banks, work she found to be “very exhausting.”
Feeling burned out, she decided to focus on another of her passions: education. Her undergrad degree was in secondary education, so that led to a career with Chicago Public Schools in their legal department.
“I was part of the transactional department, meaning that I reviewed all the contracts, any contracts that had to do with the schools, the board, or the different departments within the board,” she says. “It was very interesting because I like dissecting and reading all the fine print of contracts.”
Within a year, she was school system’s senior legal adviser. “I managed all the leases and licenses of the buildings, and that’s when I first got exposure to commercial real estate,” she says.
Kathy stayed with Chicago Public Schools for four years, until the draw of real estate began tugging at her again. She launched her career in title about 10 years ago at First American as their national commercial underwriting counsel in Chicago. She also worked as a transactional manager in the national commercial department division of a title company.
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"Dabbling in different aspects of the real estate industry helped me find my way to the role as COO. Each bit of experience has played its part."
Kathy Kwak
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Kathy thinks her rich and varied real estate and title career gives her unique experiences to draw on for the role of chief operating officer.
“Dabbling in different aspects of the real estate industry helped me find my way to the role as COO,” Kwak said. “Each bit of experience has played its part. My role as a real estate attorney, then a title underwriter, and then my experience in operations; it all contributed. I’m able to make a very good business decision because of my experience and knowledge. I have a perspective of a seller’s attorney and a buyer’s attorney. I know what they’re frustrated about. And I’m a solutions-oriented person.”
Proper Title has grown considerably since Kathy came aboard. It started with four offices and is now up to 14.
“When I started there were 50 employees. And now we’re up to 130,” she said.
The agency was established in Chicago and the north, northwest and western suburbs. She led expansion efforts with the addition of three new offices in 2021: a closing location in Orland Park, Ill., in Chicago’s southern suburbs,
an office in Schererville, Ind., to serve agents throughout Northwest Indiana, and the company’s 13th office in Crystal Lake, Ill., serving Chicago’s far northwest suburbs and marking its first location in McHenry County.
Proper Title continues to focus on expansion, Kathy said, even in the current market.
“For 2023, even if we open two more offices, I think would be a huge victory and a huge win for us,” she said.
Although the market is challenging, the job remains the same, she said.
“I just try to make the best decision for the company and for our customer,” she said. “Now, more than ever, for the sales team, one deal is a big deal.”
Kathy’s guidance has also helped the title company receive industry endorsements, including the “Excellence in Action” award from Fidelity National Title Group for the past six years. The firm also received the 2021 WOW Award from WFG National Title and was named one of Forbes America’s Best Startup Employers of 2021. It was also voted by employees as one of Crain’s Best Places to Work in 2019 and 2020.
 One of the things she enjoys about her position as COO is it gives her the opportunity to remain teachable.
“In the past two years, I’ve never learned so much about the industry and people and skill sets needed to have a successful title agency that will continue to grow,” Kathy said.
In her free time, Kwak enjoys exploring Chicago, where she’s lived for 16 years. She also loves traveling and visited Paris in June.
Her parents and a brother and sister-in-law live in nearby suburbs, and another brother, sister-in-law and 14-month-old niece live in California. She also spends time with her extended family.
“I have a very close-knit circle of friends, from high school and law school. I'm very fortunate,” Kwak said. “And even through my various jobs, I've kept in touch with people who are very good to me. I’m definitely a godmother to many.”
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