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Building Beyond the Blueprint: Women Breaking Barriers and Shaping What Comes Next

Hanna Holdings CEO Helen Hanna Casey and her guests discuss how they’re championing real estate’s next era at RISMedia’s recent CEO & Leadership Exchange.

Home Agents
By Paige Tepping
October 7, 2025
Reading Time: 4 mins read
Building Beyond the Blueprint: Women Breaking Barriers and Shaping What Comes Next

Above, from left: Helen Hanna Casey, Terrie O’Connor, Sherry Rahnama and Carol Bulman. Photo by AJ Canaria.

As more women rise to executive roles across the real estate industry, the conversation is shifting from breaking barriers to building what comes next. 

During an insightful panel titled “We Broke the Glass Ceiling – Now What?” at RISMedia’s 37th Annual CEO & Leadership Exchange moderated by Hanna Holdings, Inc. CEO Helen Hanna Casey, panelists Terrie O’Connor, Sherry Rahnama and Carol Bulman discussed how their presence at the top is changing the leadership landscape—and why succession planning is more important than ever before.

Kicking off the conversation, Casey turned to Bulman—a second-generation owner who works with three of her four adult children—to get her take on the importance of balancing being a mother and a CEO while at the same time protecting the future for her own family.

“Balancing CEO and mom is really, really tricky and really, really important,” said Bulman, CEO/chairman of the board at Jack Conway & Co., who explained to attendees that it’s one of the most important things she’ll ever do. 

“Working with my children is one of the truest joys of my life,” she added. “I absolutely love it. But I need to get it right.”

Caring deeply about the company she’s been entrusted with, Bulman said she is focused on moving Jack Conway & Co. into the next generation, as her “kids” continue working through and learning the leadership with different aspects of the company. 

“I felt I had an obligation to our company, and to my children, to be really clear about our future,” said Bulman, who notes that she owes it to her agents and her company to be as clear as she possibly can as she leads them into the future.

“What I know is my skills are in a certain category in order for my company to remain independent, if that’s what we want to do—and we have to be strong, and we have to have the right leadership in place,” she said. “These are some things I’ve been thinking about for some time.”

But in the end, it all comes back to Bulman’s relationship with her children.

“My relationship with my children is always first, and I don’t want to mess that part up. It’s a pretty wild ride, but it’s an exciting one.” 

Next, Casey turned to Rahnama—who has a completely different story, having twins a month after starting her business in 2008. 

Rahnama jumped into the conversation noting that she, like all parents, wants better for her children. 

“This isn’t an easy business, and I want them to love real estate, rather than feeling obligated to work in the family business,” said Rahnama, CEO of Virginia-based REMAX Executives. 

“I want them to have passion for it, so ideally, I would love them to go out in the world and gain the skills you need to be in leadership. I want them to go out there and find (out) if this is their true passion,” she added, underscoring the notion that being a broker/owner means knowing how to work with agents as well as the financial side of the business—rather than just selling. 

And while she isn’t quite at the point where she has the freedom to move to Europe for two years—a question Casey posed to panelists about funding their future dreams and goals—Rahnama pointed to the systems she has put in place throughout the years as a key piece of the puzzle as far as keeping the operation running smoothly.

“It’s a little different for me not having family there and not having other people running it,” explained Rahnama, “but COVID was a great thing for us in some ways because we put systems in place where we can still manage the company and still run the brokerage from wherever we are.”

Never expecting her children to join her, O’Connor founded her company in 1991 after a successful career in real estate sales, marketing and management—with three of her four children involved in Terrie O’Connor REALTORS®’ day-to-day business operations today. 

“That wasn’t even an expectation I had,” said O’Connor, who added she also thoroughly enjoys and loves working with her children. 

With no intention of leaving the real estate business she’s built behind, O’Connor noted that while the idea is for the company to continue to go on with the “children” being paid for the roles they play while at some point having the entire company to manage, charting a path forward is critically important. 

“The biggest thing for me, and I can’t speak for anybody else’s company, is having the children identify the path they want to take,” explained O’Connor, who said she feels pretty secure about the future—clarifying that people still have to navigate and move with what happens in the industry.

“I feel very, very blessed to be in the situation that I’m in, to have my kids, to have a wonderful support team and wonderful agents,” said O’Connor. “The world changes, and tomorrow everything could be different, and I can tell you something other than what I’m saying now, but right now, we’re in pretty good shape. And certainly my children, kids, whatever you want to call them, are all there and will support anything that happens in the future.”

Wrapping up the conversation, Casey emphasized the importance of women across the board, no matter their position, valuing themselves fully.  

“I don’t want any of the women, by the way, in this room—whether you own the company or whether you’re part of the company—to undervalue yourself, because we wouldn’t have men saying the same things,” she said.  

Tags: Business DevelopmentCarol BulmanCEO & Leadership ExchangeCEO ExchangeGlass CeilingHelen Hanna CaseyMLS NewsfeedReal Estate Business DevelopmentRISMedia’s CEO & Leadership ExchangeSherry RahnamaTerrie O'Connor
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Paige Tepping

Paige Tepping is RISMedia’s senior managing editor.

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