Redfin is about to get a new second-in-command, all the while continuing its efforts to be consumers’ preferred one-stop real estate shop.

Redfin has been on a roll.

From its origins as a simple portal and online brokerage, the company has in recent years become a mortgage provider, home improvement company and an iBuyer. The iBuyer program RedfinNow, has even become a trailblazer in the fast-growing segment by pushing into pricey markets that other cash offer companies have traditionally avoided.

Now, the company is also in a transitional period, with longtime executive Scott Nagel moving toward retirement. And at the same time, Redfin is continuing its quest to streamline the real estate transaction and offer consumers a different business model than they’ll find elsewhere.

With that in mind, here are five leaders at the company to watch at this pivotal moment.

Adam Wiener, chief growth officer

Adam Wiener

Wiener is currently Redfin’s chief growth officer, but he’ll only have that job for a few more weeks. Thanks to Nagel’s retirement, Wiener will be promoted to president of real estate operations next month. The job will make him second in command after CEO Glenn Kelman.

The new role will be the culmination of a long career at Redfin. Wiener first joined the firm in 2007 after a five-year stint at Microsoft. By 2011, Wiener had been promoted to vice president of analytics and new business, and he became chief growth officer almost six years ago. Over all this time, Wiener has overseen Redfin Mortgage and iBuying program RedfinNow, helped found a partner program, put together the company’s first analytics team and taken on an array of other tasks.

In a conversation with Inman last year, Wiener explained that his current job involves bringing “our mission and brand to life in our advertising” and enticing consumers to use Redfin agents.

Wiener further told Inman in March that he has stayed at Redfin for nearly 14 years because of the company’s high-performance, team-oriented culture, and because the company is “amazing.”

“We aspire to be the best employer in real estate” he said.

In his new role, Wiener will continue to oversee mortgage and iBuying operations. He’ll also begin overseeing the company’s brokerage and title work. When Redfin announced Wiener’s promotion earlier this month, Kelman praised his “understanding of our people, data and systems,” adding that such knowledge will “help us move fast on decisions that span our software and our service.”

Speaking of his upcoming new job, Wiener said he is looking forward to continuing to build out Redfin’s “one-stop-shop,” further expanding into the luxury market, and generally building the company.

“What’s amazing is I feel like we’re only at the beginning,” he added.

Jennifer Chao, vice president of engineering

Jennifer Chao

Chao first joined Redfin in 2008 as a senior software engineer. Back in 2015, she told Inman that she had been working in enterprise software, but moved into real estate technology because she wanted to “work on something more impactful.”

Chao’s early work at the company involved improving the experience consumers have while searching Redfin’s website. She also played an integral role in developing the company’s mobile app. By 2014, Chao had been promoted to a director position in Redfin’s San Francisco office, and she became a vice president in 2016.

Today, Chao’s projects include working on the company’s tours, growth and home services products. She leads the mobile app and web teams, and is in charge of Redfin’s efforts to automate and streamline the experience of booking a home tour — all things that are helping her accomplish goals she’s had at the company for years.

“My goal,” she told Inman in 2015, “is to help homebuyers and sellers make smart and informed decisions, and to make it super easy for buyers to get into homes quickly.”

Wiener told Inman that Chao is the “kindest and most caring manager you have ever met,” and that her team “absolutely loves her.” And she’s a master of the company’s technology.

“She is this incredible technical architect who has built some of our most complicated systems,” Wiener said.

Daryl Fairweather, chief economist

Daryl Fairweather

Regular Inman readers will probably recognize Fairweather’s name from the many times she has appeared in previous stories breaking down market trends and helping make sense of the economy. Especially during the tumultuous last year, Fairweather has been one of the primary voices bringing an empirical perspective to chaotic times.

Fairweather joined Redfin in late 2018 after working at Amazon. At the time she joined the company, she told Inman that earlier in her career she spent time as a researcher interviewing homeowners impacted by the financial crash of 2008. The experience “really helped me see the personal impact of housing and how entering into a decision like that can really affect someone’s life,” she said.

She also said at the time that she was drawn to Redfin in part because the company has “a brokerage attached, so I can go talk to agents, homebuyers and sellers and hear their personal stories about their experience buying and selling homes.”

Prior to working at Amazon, she earned a Ph.D in economics from the University of Chicago.

Though Fairweather’s most publicly visible role is perhaps talking to journalists — she has also appeared in the pages of the New York Times, the Washington Post and as a commentator on numerous TV news programs — she isn’t just a spokesperson. Indeed, Wiener described her as “the big brain behind Redfin,” and said the company relies on Fairweather’s insights to guide its strategy.

Tom Lewis, senior director of real estate operations

Tom Lewis

Lewis is another Redfin long-hauler, having been with the company now for 11 years. He began his stint at the firm as an agent in the Washington, D.C., area and over nearly three years in that position sold roughly 150 homes. He gradually worked his way up the company, first becoming a manager and then moving to an office in Philadelphia.

Lewis has been in his current position for just over a year, during which time he has overseen sales operations in more than 10 different Redfin markets. He leads multiple teams within the company, including those focused on helping local leaders connect with customers.

“This is probably the most exciting part of my job,” he said in an email. “There’s nothing better than collecting quantitative and qualitative research and then feeding it back to the brokerage to improve the overall customer experience.”

Lewis also led Redfin’s COVID-19 response work.

Wiener praised Lewis for rising up the ranks of the company and described him as “an amazing sales leader.” He also said Lewis is an “incredibly hard worker” who “holds his team accountable for amazing results.”

Jason Aleem, vice president of RedfinNow

Jason Aleem

Aleem first started at Redfin as an agent in the Dallas area in 2010. Wiener actually hired him, and told Inman that he did the interview in a diner on a sweltering day. Wiener showed up in business casual, but Aleem cut a figure in a suit and tie — leaving an impression with Wiener to this day.

That interaction secured Aleem a job as the first agent in the region, and after about two and a half years he was promoted to a management position. He became head of operations for RedfinNow in 2018, and was promoted to vice president of the iBuying program just last September. That means he heads up day-to-day operations for the program.

During his time leading Redfin’s iBuying program, Aleem has also served as one of the program’s public advocates. For example last fall, as the pandemic raged, Aleem touted RedfinNow’s ability to “provide a safe and convenient way for people to get a competitive cash offer for their home.”

Wiener told Inman that Aleem is especially good at big, strategic thinking — sometimes even “calling me super late at night to say, ‘Hey man I have a bunch of ideas I need to talk to you about.'” But unlike some strategic thinkers, though, Aleem is also good at following through.

“He is an incredible executer,” Wiener said, “where he’s like, ‘This is what we need to do to grow the business.'”

Correction: Tom Lewis is based in Philadelphia. This post initially misstated his location.

Email Jim Dalrymple II

Glenn Kelman | Redfin
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