Adding nuance to our weekly Teams Beat newsletter, January is Teams Month at Inman. Find out if you should join a team, what it takes to build one from scratch, and when to consider leaving. Plus, the coveted Inman Power Player Awards as well as the second class of New York Power Brokers and MLS Innovators awards.
The award-winning Chestler Jacobs Team, led by Jessica Chestler and Ben Jacobs, specializes in luxury real estate services across New York City; Brooklyn, New York; South Florida; and The Hamptons. Their partnership over the past five years has allowed them to put their lifelong passion for real estate to work for clients in some of the country’s most desirable markets.
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Learn how this award-winning team got started, where they’ve been challenged and what they’d suggest to other teams and team leads just starting out.
Team Name: The Chestler Jacobs Team at Douglas Elliman
Title: Ben Jacobs, licensed associate real estate broker and Jessica Chestler, licensed real estate salesperson
Experience: 20 years
Location: New York, New York, and Miami, Florida
Brokerage name: Douglas Elliman
Sales volume: $2.5 billion
Rankings and awards:
2024 Ellies Awards for The Chestler Jacobs Team
- Pinnacle Award: Top 3 percent of agents nationwide
- No. 4 small team (volume)
- No. 8 small team (GCI)
- No. 11 small team (transactions)
Ranked in 2024 RealTrends Verified Top Agents and Teams
2023 REALTrends + Tom Ferry America’s Best Real Estate Professionals
What do you wish more people knew about working in real estate?
Jess: It’s not easy. It might look like fun — and a lot of the time, it is — but doing it at the level top brokers do is a 24/7 job. It can be tough on personal lives because it’s not a typical 9-to-5 role. That said, it’s incredibly rewarding.
The reason it’s around the clock is that you have to be available when your clients are. There’s often a perception that it’s all about big commissions with minimal work, but in reality, our days start the moment we wake up and don’t end until we go to sleep.
Even when our trips look like vacations, we’re usually working in some capacity.
How did you choose your brokerage?
Jess: Ben and I didn’t join Elliman together, though we were both interviewing around the same time and had similar goals for our careers, which led us to the same place.
Personally, I saw it as a great opportunity to expand my network into other top-tier cities, which has been invaluable for my clients. We’ve built strong relationships with brokers in every major city, and that’s been a huge asset.
For Ben, the focus was on South Florida and Elliman’s strong presence in the market. Since partnering five years ago, both of these factors have been incredibly important and beneficial for our business.
How did you get your start?
Jess: I’ve always had a passion for real estate. Even as a kid, I’d ask my parents to take me to open houses. But I never really saw it as a career option at first. I went to school for sports communication and broadcasting, and after graduating and getting job offers, I realized that wasn’t the path for me.
That summer, I was helping my parents find a place in the Hamptons and had organized a tour. When we met the broker, they asked how long I’d been in real estate — it was a lightbulb moment for me. I went home, signed up for the real estate course and the rest is history.
I feel fortunate to have started right out of college and have had the opportunity to experience real estate as a full-fledged career.
Ben: Real estate has been in my family for over 50 years, with my family focused mainly on acquiring residential and commercial properties in Vermont to rent out. While I always knew I wanted to work in real estate, I didn’t initially see myself becoming a broker.
After college, I moved to New York City, where a cousin of mine was working as a broker for Corcoran. That sparked my interest and motivated me to get my real estate license and give it a try. Fourteen years later, I’m still here in New York, working as a top broker, and I’ve never looked back.
Tell us about an epic fail you’ve experienced. What did you learn?
Ben: One of the biggest challenges has been hiring the wrong people. Building a team is far more difficult than we initially expected. We’re salespeople, not managers, so learning how to manage people has required an entirely different skill set from selling.
Over the years, we’ve realized that hiring the right people and fostering longevity within the team is crucial to growing both your team and your brand successfully. It’s not just about finding competent, driven and hardworking individuals — you also need people who are honest, loyal and open communicators.
We’ve learned that many people, like buyers and sellers, often don’t speak their minds. It’s the same with agents. Team members must feel comfortable bringing up any issues or concerns directly with us as team leaders. We’re not mind readers, so if someone can’t communicate openly, it’s best to part ways sooner rather than later. Otherwise, you’ll waste time down the road trying to figure out what they want.
What’s your top tip for newly formed teams?
Ben: Our operations manager, Haley Ellis, has been with us for a year and has made a tremendous impact in organizing the team and helping us hire the right people.
One of the best investments a newly formed team can make is to spend the money on hiring a top-notch operations coordinator to handle the day-to-day functions of the business. This role is critical, but also one of the hardest to fill, because it requires a very specific type of person.
Managing operations for a residential real estate team is no easy task — you need someone who is incredibly organized, detail-oriented, and genuinely enjoys running the show. Most people aren’t suited for this kind of role.
We’re doing over 70 transactions a year, so you can imagine how busy Haley is. This position is what will help you scale your business and maintain organization as you grow.
English (US) · 