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Jason Aleem is no stranger to a leadership role — from helping grow Redfin’s brokerage business, to leading its iBuying platform, and now back again.

In February, Aleem was named the Seattle-based company’s senior vice president of real estate sales after spending three years as vice president for its iBuying business, RedfinNow.

Inman spoke with Aleem over the phone ahead of his appearance at the upcoming Inman Connect New York conference in April. He discussed what he learned from his perch atop RedfinNow, as well as priorities for the brokerage side of the business.

This interview has been edited for length and clarity.

Inman: You went from vice president of Redfin’s iBuying platform to head of the company’s sales operation. What was behind the switch, and what insight are you hoping to bring to the new role? 

Jason Aleem: It was a homecoming, honestly.

I started my career with Redfin in November of 2010. So I went over to the iBuying operation RedfinNow just three-and-a-half years ago in 2018. That was a departure from what was home in regards to brokerage sales. So my experience in regard to scaling and growing Redfin, the majority of the time, has been on the brokerage side.

And then getting to go over and scale the iBuying business was amazing. Just being able to be atop of a business by leading strategically, building the structure out and scaling it, was an amazing training ground and opportunity to operate at a higher level.

When an opportunity opened up back at the brokerage, it just made sense.

Did you learn any lessons from the iBuying process that could add to what you bring to this new role?

Tons of lessons. I’m leaning on them all the time right now. Some are internal; some are external.

Internally, I just really loved growing our strategy and our operations and sales teams together. That’s one of my favorite things that’s happening right now, is bringing our teams closer together.

Externally, getting the chance to see what customers want, being able to see the customer experience up close and personal as we were building it out at RedfinNow, and really studying a lot of the competition. Seeing where the early adopters were going in regards to innovation was exciting to see, and helps me understand what kind of things that folks that are deciding not to take a cash offer — but still list their home — what they’re going to want in that experience.

So I can lean on some of those things, whether it’s seeing the software integration, or whether it’s the right questions being asked in the early stage when a customer is deciding to search and then convert over to working with us or any company, seeing what that frictionless experience is like and what people want.

And then just understanding more and more what our [employees] want. I felt like I was in the trenches, and I like being in the trenches and working with our people and really understanding what’s on the ground floor. 

With the collapse of Zillow Offers and the expansion of Opendoor and RedfinNow, what did you learn along the way about the pitfalls of iBuying, but also the opportunities going forward?

It’s a high-stakes game. It’s high pressure at all times within the iBuying space, just because it’s a risk that each of our businesses are taking in regards to owning real estate.

You think about us and our history, it’s brokering deals. It’s a different thing when you actually become a principal in the deal. Slow and steady, I think, can still win the race, and this space is going to continue to grow and develop over time. We committed to taking that route where we wanted to give sellers choice where they can list their home with us or take the cash offer. And we’re comfortable with growing over time and making sure that we’re being methodical and making sure that we’re managing our risk well. And it kind of proved out this year that that was a wise route to go versus the blitz-scaling approach that others decided to take.

But then it’s also interesting just to see if the market started to level out at times, how things played out. All iBuying businesses mostly have been born in a really hot market, over the last seven years. What’s the play when things are starting to get not as steaming-hot as what they’ve always been? That was something that we needed to learn throughout the years as prices moderated in certain parts of the country.

But the biggest thing, I would say, is that no matter what’s going on in the market, this level of convenience and certainty that comes from a cash offer, I think it’s here to stay. I think people want it. People really are willing to pay for that convenience. As there becomes more parity between the products, I think that’s going to continue to grow the market share of iBuyer transactions versus traditional.

Now that you are fully in this new role, what are the goals that you have, or the big-picture opportunities on the horizon for Redfin’s sales operation?

There’s still a melding between the iBuyer operation and the people seeking cash offers, but then eventually listing, that we need to glue together, and make sure those products speak together well and that customers have the choice. It exists now, but it’s just on the other side of the equation. There’s a lot that we can do for our agents in regards to making sure that we’ve got the best agents in the industry.

At the end of the day, customers need guidance. Customers need support and expertise to get through these transactions in a really tough market. When that rubber meets the road, you can have the website, you can have all the apps and all these different things — they’re going to need an agent on their side. They’re going to need an advocate that can really help them understand how to navigate a transaction — win it first, and then navigate that transaction successfully, move into that home.

So really focusing on making sure we’ve got the best agents in the industry is priority No. 1, in regards to how I’m thinking about things.

I’m wondering too if you’ve been given any guidance from the company on specific goals, for either recruitment or anything along those lines, that you’d like to see accomplished in the next year or two.

Yeah we’ve talked some retention and some attrition goals that we want to hit for sure. Those are internal goals. Those are things that we’re focused on making sure that those things happen.

One of the big things that everybody’s aware of in regards to our Bay Equity [Home Loan] purchase, that’s a big one where we want to integrate them into our service offerings, make sure that we’ve got the one-stop shop where customers can come to Redfin and get everything done. You start thinking about one-stop shop and making sure our agents understand how to glue those products together for our customers, and making sure our customers really are excited about us providing another level of convenience, certainty and potentially cost savings as well as we put those products together. Those are some of the top things.

But the big mandate is, make our agents as amazing as possible. Agents are still at the center of everything we talk about, and at the center of the transaction. And at the end of the day, we have to make sure they’re amazing. We’ve got to make sure that we have great first impressions, and that our agents are really good at building trust and building confidence with customers so that they can be successful.

With Inman Connect New York coming up in April, can you give our readers a sneak peak of what you plan to discuss at the conference?

We’re excited about the future of what we’ve got going on at Redfin. We’ll press on what agents want in the industry right now. Hopefully we’ll touch on the future of where things are going. A little bit more of a sneak peak, behind-the-curtain with Redfin as well. And then just what we think it takes to win in this environment. So those are some of the top things we’ll cover.

Email Daniel Houston