Jen Caskey

My Local List

• Favorite Mexican: El Sombrero
• Favorite Dog Walk: The Greenbelt
• Favorite Seafood: Fishing With Dynamite
• Favorite Shopping: Wright’s Manhattan Beach

The Jen Caskey Group at Compass is a real estate team specializing in luxury residential properties throughout Manhattan Beach, Hermosa Beach, Redondo Beach and Palos Verdes. Jen Caskey founded the group in 2022 and began her real estate career in 1991.

Tell us about your background.

I grew up in Manhattan Beach, attended Robinson Elementary and Mira Costa High School, and graduated from the University of Southern California. My mother was a local Realtor, so real estate was part of my life from an early age. After USC, I began my career in 1991 and have since represented generations of South Bay buyers and sellers, building a business centered on relationships, discretion and deep local expertise.

What top traits make a great business leader?

A great leader needs integrity, enthusiasm and the willingness to listen. I also believe the best leaders set a high standard through their own work, communicate directly and give their team the trust and support to excel.

How does authenticity play into your work?

Authenticity is at the center of our business because real estate is deeply personal. We give clients honest advice, even when it is not the easiest answer, and we build relationships that last well beyond a transaction.

Who opened a door for you professionally that made a huge impact?

My mother opened the first door for me. She was a successful Realtor in Manhattan Beach and taught me the value of preparation, hard work and treating every client with care. Today, I am proud to create opportunities for the women on my team and for my son Shane, who brings a new generation of leadership and perspective to our business.

How do you attract and retain the brightest minds to be on your team?

We have created a culture where talented people are trusted, supported and encouraged to contribute their individual strengths. Our team members share information, celebrate one another’s wins, step in for each other and build their careers here.

What services do you offer?

Our services include buying and selling, private and off-market acquisitions, discreet listing representation, lease representation, and specialized advisory services for sports and entertainment clients. We bring highly personalized representation and sophisticated marketing to each transaction.

What is your current passion project?

I am especially excited about expanding JCG Sports & Entertainment, a specialized division serving athletes, entertainers and other high-profile clients who value privacy, discretion and a seamless experience. It is a natural extension of the trusted, highly personalized representation our team has always provided.

When people tell the story of your business years from now, what do you hope they’ll say?

I hope they say we were exceptional at what we did and kind in how we did it. I want the Jen Caskey Group to be remembered for lasting relationships, meaningful community involvement and helping people feel truly at home in the South Bay.

How can we support other women in business?

We can recommend, hire and mentor women and speak their names in rooms where opportunities are being discussed. Support is most meaningful when it is consistent and specific—not just encouragement, but real introductions, advocacy and opportunity.

In what ways do you stand out in your field?

We are highly local. We know so many people in town, we make a point of supporting our local businesses, and we understand what makes each neighborhood and street special. Most importantly, our clients become long-term friends, and those lasting relationships are at the heart of our business.

What does “local” mean to you?

Local means home. I grew up in Manhattan Beach, raised my three boys here and have spent my career helping people become part of this wonderful community. It means running into friends and clients around town, supporting the businesses we all love and welcoming new neighbors who often become lifelong friends.