In 1 Year, Orchard Doubled Their Headcount From 300 to 600

Here’s how the company maintains their culture with so many fresh faces.

Written by Brendan Meyer
Published on Jan. 10, 2022
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When Rahil Esmail first visited Orchard’s New York City office for a job interview three years ago, he wasn’t greeted with a huge space, floor-to-ceiling glass windows, and a sprawling view of the Big Apple. There was no cold brew coffee on tap or a game room filled with ping pong and foosball tables.

Orchard’s office was inside a walk-up apartment.

Esmail ascended the staircase and entered the two-bedroom flat where 30 or so Orchard team members worked inside. There was a living room lined with desks, a bedroom that had been converted into a boardroom, and another bedroom that had been turned into a conference room.

“The bathroom had a bathtub in it,” Esmail said. He loved it.

Esmail, the head of consumer product at Orchard, thrives off of the energy of startup culture. The smaller the place, the more energizing it feels, he explained.

“Because it means this is a chance at building something from the ground up that doesn’t exist,” Esmail said.

But Orchard isn’t so small anymore. 

The real estate company that’s transforming ​​the way people buy and sell their homes has grown tremendously since Esmail joined, especially in the last year, in which Orchard doubled its staff from 300 to 600 and reached unicorn status. 

The days of cramming their workforce into a walk-up are long gone. Orchard now has offices in cities like Austin, Atlanta and Denver. In early 2022, employees will be moving into a new office in New York City on Broadway.

“A couple months ago, I was at the Austin office and I was like, ‘I can’t believe this is where I work,’” Esmail said. “It was really cool and exciting to see.”

In 2022, Orchard will expand its markets to Seattle, Portland and Phoenix, meaning dozens of new hires that will need to acclimate to the company culture. So how does the unicorn company maintain its unique characteristics with so many fresh faces? Built In NYC spoke with three employees to learn more about how they’ve seen Orchard evolve — and how it’s stayed the same — amidst massive scale.

 

WHAT THEY DO

Orchard offers three stress-free ways to help you buy and sell a home, including its “Move First” service, “Buy and List” service and its “List” service.

 

What makes Orchard’s culture unique?

Rahil Esmail, head of consumer product: We’re constantly taking big swings, and experimenting with new ideas quickly. It’s common for companies to slow down as they scale, but at Orchard we’ve managed to retain our pace of innovation as the company has grown from 30 to 600 employees over the last three years.

Caitlin Perkins, Salesforce administrator: It’s so exciting and rewarding to work in a fast-paced and collaborative environment — especially when everyone you work with is so good at what they do. I love that we’re open to new ideas, always learning, improving, and making it a point to celebrate each other’s success along the way.

Carnesha Craft, associate general counsel: To me, what’s so unique about Orchard’s culture is how fiercely protected and highly regarded it is. This was evident to me from the first interview and has proven true time after time in the last eight months. Every person I have met at Orchard has been low ego, high producers and a hundred percent committed to delivering moments of magic and delight not only to our customers but also to each other. That’s pretty special and not something I’ve seen on a broad scale at many companies.

It’s common for companies to slow down as they scale, but at Orchard we’ve managed to retain our pace of innovation.’’

 

How have you seen Orchard evolve?

Esmail: When I joined the company, the only service we offered was buying homes directly from people who were looking to sell. Now, we have integrated the brokerage, mortgage, and title experience, and offer unique services for all consumers, whether they are looking to buy, sell, or both. 

The fundamental service that we offer and who we can actually serve has completely changed. The other thing that’s changed is the credibility of the brand. A couple of years ago, nobody knew Orchard. We had low single digits of reviews on our website. It’s hard to scale a brand when you’re starting from square one, so it’s really nice to see how much brand credibility we’ve built over such a short period of time

Perkins: I was employee No. 70-something. Along with our evolving headcount and the services we provide, what also stands out is having a people team. When I joined we had some great local office leadership, but we didn’t have a human resources department. Now, we have a fully developed people team. Throughout the pandemic, our people team has done a fantastic job supporting everyone, keeping us engaged, and our culture intact.

Craft: I joined the company in May 2021, and I was employee No. mid-300s. The idea that we doubled so quickly is kind of crazy. A few weeks after I started, we trained a class of 70 new hires, and during a meeting shortly after one of my coworkers was like, “You’re not the new person anymore. You’re part of the old guard.” Obviously it wasn’t true, but in a weird way it felt like it was.

 

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SHUTTERSTOCK

 

What's the most exciting aspect that comes with growth? 

Perkins: An ownership mentality. I feel like I’ve had a hand in helping this company grow and scale throughout its journey. Growth will always present new problems to solve and at Orchard, everyone is encouraged to bring ideas and run with solutions. I’m a problem-solver at heart so growth is definitely exciting. 

Esmail: The fact that we’re able to serve more people, and in a better way, is exciting to me. Back when we were 30 people, our only market was Texas. Now, we’re in four times as many markets as we were, across several states.

It’s also exciting to have expertise on the team that I can lean on and know that there’s somebody who can do a job much better than I can. For example, when we were launching our buy-side program (helping buyers search for a home), we had to integrate with all these multiple listing services (MLS). MLSs are companies that have databases of listings that are on the housing market. I remember spending a six-hour flight reading through tons of contracts, for every MLS, and trying to understand them. I had this giant spreadsheet. Why did I do all of this? Because we didn’t have a legal team at the time. Now, it’s nice and exciting to have people who are much stronger at stuff that I’m not as well-equipped to do. 

Craft: I love that we’re soon going to be branching out into new markets. Since I am relatively newer than those who had a hand in previous market expansions, the excitement I feel having a hand in the growth and scaling of the company is what I imagine those that were here before me felt years ago.

 

 

And the challenges?

Perkins: One challenge is getting new hires up to speed. When you’re trying to operationalize something at this level, training and onboarding is important to make sure everyone can be effective in their role. Luckily, we have some great leadership in place that keeps a pulse on that and is open to feedback. We’ve also invested in learning and development tools to help make training and onboarding easier.

Craft: With more people comes the need to be thoughtful and the need to have more intentionality behind our actions. We’re no longer just turning a speedboat around, so to speak. Now, we’re turning a yacht around, which often takes a little bit more time and the need for flexibility.  

Esmail: The challenge is, we’re not slowing down. We want to make sure we’re continuing to innovate and move fast in an environment where we’re larger. That can make things challenging, but it’s definitely something that everyone’s excited to tackle.

We’re no longer just turning a speedboat around, so to speak. Now, we’re turning a yacht around, which often takes a little bit more time and the need for flexibility.’’

 

PERKS

Want to buy a home? Be prepared to save some cash, thanks to Orchard’s employee discount program. Employees receive a discount on the fees that a customer would normally pay to sell or list their home.

 

How does Orchards mission resonate for employees who live in cities like New York where renting is more popular than buying?

Craft: Buying a home is a super complicated process, and we’re removing some of the friction that inherently exists in the industry. By making this process simpler, we’re also increasing homeownership access for more people. That resonates for me.

Esmail: It’s a problem that’s worth solving, whether you currently face the problem or not. Everyone knows someone who has bought a home, and the frustration surrounding that process is widespread. It’s an exciting problem to solve. 

At Orchard, it’s also important for us to be close to our customers, even if we’re not physically living in the same market as them. We have many ways that we do this, whether that is flying to our markets or interviewing customers on Zoom. We’re constantly trying to empathize with people wherever they are.

 

Responses edited for length and clarity. Photography provided by companies listed, unless otherwise noted.