Joey DeBenedetto


Joey appears in the Top 100

People in Real Estate Magazine

DeBenedetto, Joey.jpg

Joey DeBenedetto


Joey DeBenedetto is CEO of two successful Keller Williams offices in California: KW Cupertino and KW Palo Alto. Under his leadership, the offices produce revenues in excess of $150 million per month through residential and commercial sales. The Palo Alto and Cupertino office employs 350 agents who specialize in luxury properties. Both offices have been ranked among the Top 500 Brokerages in the U.S. by Real Trends.  Joeys offices with Keller Williams were also named, The Most Innovative Real Estate Company in 2019. Recently, Joey and his team partnered with New Story, a company featured on the Apple TV series, Home, to help those affected by COVID-19 pay their rent and keep their housing. Joey’s offices have donated thousands of dollars towards the efforts to end homelessness and support their local community.


When Joey first took over KW Cupertino, the struggling office was losing eight agents per month and in need of a strong leader who could rejuvenate operations. Under Joey’s direction, they catapulted to the top 10. Because of his immense success, he was soon appointed as CEO of the Palo Alto office as well.


With expertise in real estate, entrepreneurship, and technology, Joey also serves as a real estate coach, helping the #2 agent by commissions in all of Keller Williams build his business. “The most significant difference between working as an agent and serving as CEO is the requirement of not only staying up-to-date on the market, but also projecting where it is going in order to make decisions that will affect 300+ other people,” Joey explains.


Although Joey has acquired extensive practical skills as a salesperson and executive, his earliest experiences were creative in nature. After earning a degree in musical theatre, he performed with international symphonic tours and in New York City’s iconic Broadway district. The lifestyle, however, became unsuitable and as his interests and goals evolved, he knew his career needed to as well. The catalyst for his career change came, like many, after he saw the show, Million Dollar Listing. He was ready for a shift. Joey then completed the training and coursework for real estate sales and joined Century 21, a boutique firm in Manhattan. At first, Joey earned barely enough to survive on, and was forced to build Ikea furniture just to pay the rent. Realizing that change had to be made, he refocused his efforts and formed a team. While successful in real estate sales, unfortunately, Joey’s partnership did not work out and he left to join Nest Seekers International. Although he was now a ‘solo act,’ the move proved to be a smart one. He doubled his business in less than one year. After acquiring more knowledge of operations, Joey set his sights on Silicon Valley. He moved to California, with the hopes of obtaining his real estate license, and creating a bi-coastal real estate team.


Now, as a thriving real estate expert, Joey is compelled to share his success and experience with his team as well as those who intend to pursue a career in the field. He coined the phrase, “Join the Revolution” to encourage others to excel. “Most managers just skate by, doing the bare minimum required of them. Leadership skills are different from sales skills. I support my staff and colleagues to facilitate success for them in the long term. The industry is shifting, agents are being eliminated and replaced by technology. I want to make sure there are viable solutions for my people, even as we evolve,” says Joey. To that end, Keller Williams has partnered with tech companies such as Facebook and NextDoor to make it easier to reach more people, find agents, and share accurate data. Facebook and Google, for example, are now strategic partners.


Joey’s journey from a successful performer to a successful real estate agent to industry mogul is the quintessential example of what can be accomplished through hard work, perseverance, and ambition. Fortunately, he freely shares his knowledge and expertise so that others can learn and prosper from his experience. 




Joey DeBenedetto

CEO and Team Leader

Keller Williams Cupertino | Keller Williams Palo Alto      

websites:   |


LinkedIn: Joey DeBenedetto

Download the magazine and see Joey's feature on page 82.

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