Jen Caskey

The Jen Caskey Group at Compass is a boutique real estate group specializing in luxury properties in Manhattan Beach, Hermosa Beach and Redondo Beach. Owner Jen Caskey and her team have more than 30 years of real estate experience. Jen started working in real estate just after graduating from the University of Southern California and has worked in the industry ever since. She started The Jen Caskey Group in 2022 and had more than $160 million in sales that year.

What inspired you to pursue a career in your field?

I would have to say watching my mom have a successful career in this industry was my main motivation. She was a Realtor^® in Manhattan Beach, so I learned from the best! My sister is also a part of our team, so it’s always been in our family. I’ve been in business in this community for 30+ years. I have a passion and commitment to our industry and dedication to serving my clients in the South Bay. My team and I pride ourselves on our client service and attention to detail and love working in our hometown.

What are the benefits of having women in leadership?

Women leaders bring a different perspective to businesses, and in leadership positions we are uniquely qualified to lead with intelligence, competence and attention to detail. Women are often great communicators as well. If you are formidable enough to craft a direct approach, you can accomplish great things for your clientele and team members.

What are some key qualities for women in leadership roles?

I believe women in leadership roles need to lead by example. For me, that means focusing on client communication and service, and demonstrating a desire to give back to our community. My goal is to empower my team members to represent our group in the best way possible through a shared passion for real estate and dedication to the South Bay communities. 

Share a significant accomplishment in your career. 

Starting The Jen Caskey Group at Compass was a significant accomplishment for me, and I am so proud to be doing business in my hometown with extraordinary people behind me. We’ve all worked hard to establish a new group here, and I could not have done it without them! We are very excited about our unique approach to luxury real estate. Our tagline says it all: Luxury Boutique. Global Reach. We absolutely love what we do and enjoy developing our platform to reflect the changing trends within the industry.

What are the roadblocks to taking good care of yourself?

Like everyone, I get busy and time flies. I need to remind myself to focus on taking time out. I love spending time with friends and family to unwind—that’s my favorite way to take care of me!

What does success mean to you?

For me, personal success is seeing my boys happy and healthy and thriving as they make their way into their own lives. That’s my #1 priority. Professionally, success means happy clients who become friends, whom we often help buy and sell homes more than once. Finally, working with my incredible team and the effort they put in every day has led to our success as a group.  

How do you rally your team to take on a big goal?

Thankfully, that’s an easy task as we all like to rally around each other when we have a common goal. Whether that’s a unique transaction or participating in a charity event, our team is awesome at supporting each other.

How do you foster a positive work environment?

Attitude is everything, and when you love what you do, it shows! Every one of our team members demonstrates a positive attitude daily, and for that I am grateful. We all count on each other to be supportive, have each other’s backs and take a break when needed.

What local hot spots do you share with visitors from out of town?

Fishing With Dynamite is one of my all-time favorite local haunts, and I love introducing new people to their delicious food and fun vibe. I also love Wright’s for unique finds and Petros for a fun night out with friends.

What motivates you to go to work every day?

I would say my family—my three boys especially—motivate me, as well as a true passion for helping people find their dream homes. I am very lucky to have found a profession that is so satisfying and allows me to assist my clients with one of their biggest investments, in an area I feel fortunate to live in myself.  

Where do you see yourself in the future?

Right here, doing what I love best to give our clients an unparalleled experience in finding, buying and selling a home. I see myself working with the members of our team for and with our community and enjoying my boys as they get older and start families of their own.

Photographed by Lauren Taylor