Adding nuance to our weekly Teams Beat newsletter, January is Teams Month at Inman. Find out whether you should join a team, what it takes to build a team from the ground up, and when to consider leaving. Additionally, he will receive the coveted Inman Power Player Award, the New York Power Brokers Award and the second class of the MLS Innovators Award.
The award-winning Chesler Jacobs team, led by Jessica Chesler and Ben Jacobs, specializes in luxury real estate services throughout New York City. Brooklyn, New York. South Florida. And the Hamptons. Our partnership over the past five years has allowed us to leverage our lifelong passion for real estate for our clients in some of the most attractive markets in the country.
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Learn how this award-winning team got started, where they face challenges, and what they offer to other teams and team leaders just starting out.
Team Name: Chesler-Jacobs Team at Douglas Elliman
Title: Ben Jacobs, Licensed Associate Real Estate Broker, Jessica Chesler, Licensed Real Estate Salesperson
Experience: 20 years
Location: New York, NY and Miami, FL
Securities company name: Douglas Elliman
Sales: $2.5 billion
Rankings and awards:
2024 Eriez Prize Chesler Jacobs Team
Pinnacle Awards: Top 3% of agents nationwide 4th Place Small Team (Volume) 8th Place Small Team (GCI) 11th Place Small Team (Transactions)
Ranked among Top Agents and Teams Verified by RealTrends in 2024
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 may seem like fun, and often it is. But doing it at the same level as the top brokers is a 24/7 job. It can be tough in your personal life because it’s not a typical 9-to-5 role. That being said, it’s incredibly rewarding.
The reason we’re available 24 hours a day is because we have to be available when our customers are. There’s a common perception that it’s all about getting big commissions for minimal work, but in reality, our day starts the moment we wake up in the morning and doesn’t end until we go to bed.
Even if traveling looks like a vacation, we are usually working in some way.
How did you choose a securities company?
Jess: Although Ben and I didn’t start at Elliman together, we both interviewed around the same time and had similar career goals, so we ended up in the same place.
Personally, I see this as a great opportunity to expand my network to other top cities, which has been invaluable to my clients. We have strong relationships with brokers in all major cities, which is a great asset.
For Ben, the focus was on South Florida and Elliman’s strong presence in the market. Since our partnership five years ago, both of these elements have been extremely important and beneficial to our business.
How did you get started?
Jess: I’ve always had a passion for real estate. Ever since I was a child, my parents would take me to open houses. However, I didn’t really consider it as a career option at first. I went to school for sports communications and broadcasting, but after graduating and getting a job offer, I realized it wasn’t for me.
That summer, I helped my parents find a home in the Hamptons and organized tours. When we met with our broker, they asked how long I had been in the real estate industry. That was a lightbulb moment for me. I went home, enrolled in a real estate course, and the rest was history.
I started right out of college and feel lucky to have had the opportunity to experience real estate as a full-fledged career.
Ben: My family has been in real estate for over 50 years, primarily focused on acquiring and leasing residential and commercial properties in Vermont. I have always wanted to work in the real estate industry, but at first I never thought I would become a broker.
After college, I moved to New York City, where my cousin worked as a broker for Corcoran. That piqued my interest and I decided 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 me about an epic failure you experienced. What did you learn?
Ben: One of the biggest challenges is hiring the wrong people. Building a team is much more difficult than we originally expected. We’re salespeople, not managers, so learning how to manage people requires a completely different skill set than sales.
We’ve known for years that hiring the right people and ensuring longevity within your team is key to growing both your team and your brand. Not only do you need to find talented, motivated, and hard-working people, you also need people who are honest, loyal, and open communicators.
I’ve found that many people, including buyers and sellers, often don’t express their opinions. The same goes for agents. Team members should feel free to raise issues and concerns directly with us as team leaders. We’re not mind readers, so if you can’t communicate openly with someone, it’s best to break up early. Otherwise, you’ll be wasting your time trying to figure out what they want.
What is your top tip for newly formed teams?
Ben: Our operations manager, Hayley Ellis, has been with us for a year and has been a huge influence in organizing our team and recruiting the right people.
One of the best investments a newly formed team can make is to spend money hiring a top-notch operations coordinator to handle the day-to-day operations of the business. This role is very important, but it is also the most difficult to fill, as it requires a very specific type of person.
Managing the operations of a residential real estate team is no easy task. We need someone who is incredibly organized, detail-oriented, and truly enjoys running the show. Most people are not cut out for this kind of role.
We do over 70 transactions a year, so you can imagine how busy Haley is. This position will help you scale your business and stay organized as you grow.
Email Christy Murdock
