Inside the real estate company that’s transforming communities and careers

Real estate agents aren’t just selling houses; they’re building communities. Behind every “sold” sign is a story of people embarking on new beginnings, families putting down roots, and neighborhoods flourishing with life.

That’s especially true when agents are supported by a company that cares about leaving a positive mark on the people and communities it serves. At Windermere Real Estate, a family-owned company with more than 300 offices around the Western U.S., giving back is central to the culture. It’s one of the reasons homeowners and buyers feel confident choosing Windermere agents to represent their properties and interests, and why agents are so proud to be part of the team. A true family business, Windermere’s leadership team is composed of Jill Jacobi Wood, OB Jacobi, and Geoff Wood, the daughter, son, and son-in-law of founder John Jacobi. Jill’s sister-in-law, Christine Wood, also works for the company. Together, they’ve stewarded the company’s growth into one of the largest and most respected regional real estate brands in the country, and have brought a new generation into the fold: Jill’s two daughters, Lucy and Franny, have also joined Windermere.

Since 1989, the Windermere Foundation has raised over $53 million for low-income and homeless families in the communities where its agents live and work. The company has made donations to the Windermere Foundation a built-in part of its business, with a portion of each agent’s commission going to support the nonprofit.

“When you have 6,500 agents, and everybody gives a little bit, it adds up pretty quickly,” says Christine, executive director of the Windermere Foundation. Because agents, franchise owners, and employees are the ones contributing, they decide where the money goes, Christine says. That means they get to see those funds make a difference in their own backyards, from providing new shoes and socks to school kids in Spokane, Washington to helping families in Fort Collins, Colorado stay in their homes. This local impact is further strengthened by Windermere’s annual Community Service Day, on which all offices close so the team can get out and serve their communities.

There is a sense of solidarity among Windermere agents that’s not always easy to find in the industry, Christine says. That comes in part from the collective efforts to do good in their communities — a goal everyone shares regardless of their location or role.

Lucy Wood, Windermere’s regional manager of Western Washington and Jill’s daughter, explains that starting a career in real estate can feel lonely. One of the strengths of the Windermere network is that new agents can lean on experienced agents to learn the ropes and navigate sticky situations. Forging these relationships can enrich and support their careers.

“This whole business is based on relationships,” says Jill, Windermere’s co-president. “Whether you’re working with clients, customers, colleagues, or contractors, the most important skill that you can have is how to navigate through all kinds of personalities.”

She has fostered those connections over 40 years at the company, getting her start as a receptionist before working her way up in the accounting department, becoming an agent, managing offices and regions, and later joining the executive team. Her daughter Franny, who also works at Windermere, recalls rides home from school listening to her mother on the phone with an agent who had a problem with a property or a franchisee who was having trouble getting enough water pressure from the office sink.

“I remember saying to my mom all the time, ‘Why are you taking these calls? Isn’t there someone else that should be taking them?’” says Franny. “And she would say, ‘No, these are actually the most important conversations that I have.’” Jill understood that building strong relationships with associates at every level was a powerful tool for creating a cohesive team.

After growing up steeped in the family business, the younger generation has come to appreciate the level of care it takes to build a company that only gets stronger over time. “Every decision the leadership team makes is through the lens of, ‘How is this setting up the next generation for success? How is this setting us up for longevity?’” says Franny.

Jill says she inherited this same mindset: “My dad always taught us that we are stewards of what we’re doing,” she says. “Whether it’s the foundation or our company, we are making decisions for the greater good, not for us personally, and to steward it through our generation and hopefully pass it on stronger to the next generation.”

The company also focuses on cultivating its agents’ individual talents, setting them up for long-term success. Windermere shines as the preferred real estate brokerage for agents due to its unwavering commitment to nurturing human potential in its agents and the communities it serves. Part of that is giving agents the tools to invest in themselves and their businesses so they can build fulfilling, lifelong careers. Because each office is individually owned and operated, the owners care deeply about each individual’s professional and personal life, and coach them to their success. Among the more innovative initiatives the company has designed to cultivate internal talent is a unique training program called Windermere Summit, which is dedicated specifically to mentoring and guiding new real estate professionals in the Seattle area. Summit graduates go on to join other Windermere offices empowered with the skills and confidence to excel. Though Summit is a new initiative in its testing phase, Windermere hopes to roll it out company-wide in the future.

The industry is constantly changing, and Windermere understands that its tools and programs need to evolve in tandem. To that end, says Lucy, she and her peers interact with agents in different offices every day, discussing their experiences and incorporating their perspectives into the company’s direction.

“We’re not months behind in what we’re providing for our agents,” she says. “We’re very on the ground with them, asking them what they need and making sure that we’re building those programs, classes, trainings, and coaching sessions around what they need specifically to help them in their businesses today.” In just one recent week, Jill visited four offices in four different cities — which is just the way she likes it. “It makes us excited about what we’re doing instead of sitting in a bubble.”

The company prides itself on how receptive its leadership team is to feedback. A sometimes underappreciated advantage of a family business is the freedom the younger generations can have to bring fresh ideas to those at the top without feeling like they need to hold back. After all, these are the same people who raised them to speak their minds. Franny sees it as her and Lucy’s responsibility to be in dialogue with the generation that laid the groundwork for their success, and to push them to be even better. This culture of continual growth is part of the company’s DNA.

As the company evolves, it recognizes the importance of helping its agents progress in their careers. At Windermere Real Estate, relationships matter most, and mentorship, collaboration, and community are central to building a business that will continue to thrive for generations.