Beyond the C-Suite: How South Florida's women leaders are building pathways for future generations

Business Journals

2 days ago

From real estate and tech to education and nonprofit sectors, the region's most influential businesswomen are doing more than leading — they're redefining what leadership looks like for future generations.
For women in leadership, rising to the top is rarely the final destination — it's the beginning of a new responsibility: creating pathways for others.
That was the prevailing theme at TD Bank's recent Table of Experts roundtable discussion, hosted at the bank's Broward County office and moderated by TD's Jennifer Starkey, Regional Vice President of Broward County and Casey Crist, Regional Vice President of Miami-Dade County. The event gathered leaders from real estate, construction, education, technology, and the nonprofit world to unpack what it takes to lead today — and how they're rewriting the playbook to ensure those who follow have a clearer path forward.
'Hearing women at the top speak candidly about their experiences – the wins, the setbacks, the lessons – is what makes these conversations so impactful,' said Starkey. 'The women at this table are not satisfied with being 'the first.' They're focused on not being the last.'
'This wasn't just a conversation about women in power,' added Crist. 'It was about how this power can be used — to open doors, to mentor, to challenge systems. It sends a message to the next generation watching: You belong here too.'
Breaking the mold — and rebuilding it
In industries generally thought of as more male-dominated like construction and tech, breaking barriers often means building trust from the ground up.
Kim Henderson, Senior Vice President and General Counsel at Moss — and the company's incoming Chief Operating Officer — knows that all too well. 'I've always approached litigation as a learning opportunity,' she said. 'Being underestimated gave me an edge — it meant I could surprise people.'
Joining a legacy leadership team at Moss wasn't about optics. 'I wasn't a 'check the box' hire,' Henderson said. 'Merit is the foundation here, and the company made sure to celebrate that when I was recognized as an influential leader.'
Sasha Seco Alvarez, Chief Information Officer at ANF Group, understands the balancing act — not just between work and life, but between disrupting and belonging. A veteran in construction tech with nearly two decades under her belt, Alvarez said she's 'the outlier in every way possible' — often the youngest, often the only. But that position has helped her drive change. 'Being a disruptor gives you freedom to challenge the status quo,' she said. 'And I do — daily.'
Her support system? 'My personal board of directors,' she joked — her husband, kids, and mom. That collective foundation, she said, makes it possible to lead with both vision and perseverance.
In real estate – a major hot topic in South Florida today – change isn't only happening in the market, it's happening in the boardroom.
At One Sotheby's International Realty, Chief Operating Officer Vanessa Stabile is guiding an impressive 1,300 agents through a shifting industry — one defined by evolving contracts, commission structures, and a generational reshaping of the workforce.
'Younger professionals are entering this space with new expectations,' she said. 'We have to meet them where they are — remote work, flexibility, values-driven cultures — and still maintain the highest standards.'
Her role has evolved into one of mentor and coach, helping agents view themselves as CEOs of their own businesses. 'It's not about who you are when you show up to work,' she said. 'It's about what people say when you leave the room.'
For Dionna Hall, CEO of Broward, Palm Beaches and St. Lucie Realtors, talent development is top of mind. The organization, which serves over 40,000 members, is filled with women — not by design, she said, but by culture. 'Women are natural multitaskers and problem solvers,' Hall said. 'That's what leadership in this space demands.'
Building influence with intention
Laurie Jennings, Emmy-winning journalist turned executive coach and brand strategist, believes that authenticity is at the core of influence.
'What we often see in the business world is that men traditionally network with people they can do business with. Women often network with people they just enjoy being around,' she said. 'There's nothing wrong with that — but we also need to start doing business with our friends. Know your worth. Talk price. Step into the deal.'
Jennings now works with law firms and corporations to help women professionals elevate their visibility, confidence and networks. 'Your personal brand is not just optics — it's leverage,' she said.
That's especially true in sectors like nonprofit and education, where visibility is tied directly to impact.
Linda Lecht, President of The Education Fund, said storytelling is key to engagement. 'Nearly 80% of our funding comes from the private sector,' she said. 'So we're constantly telling our story — through events, corporate sponsors, and current and future donors.'
From financial literacy, Teach-A-Thons, to the recent 'Love of Art' annual charity auction, the nonprofit aims to be both resource provider and community convener. 'When people believe in public education, they're willing to invest in it,' Lecht said. 'That's how we lift up the Miami-Dade County and South Florida communities.'
Financial institutions as force multipliers
Nonprofit leaders often act as the connective tissue between the community and corporate partners. But access to funding, mentorship and economic mobility remains a challenge — especially for women and communities of color.
Kerry-Ann Royes, CEO of YWCA South Florida, challenged banks and business leaders to see themselves as more than funders — but as force multipliers.
'We're in uncertain times across sectors, but the institutions that stand beside us — especially banks — can help us weather that,' she said. 'When we talk about workforce development, early education, financial literacy — it's all interconnected. And institutions like TD can walk beside us in that journey.'
Crist agreed. 'This is about the long game,' she said. 'Supporting one nonprofit or mentoring one woman leader today may result in systemic shifts a few years from now. That's how generational change begins.'
Starkey and Crist left the group with this:
'Leadership isn't about having all the answers,' Starkey said. 'It's about being willing to share what you've learned and making space for others to grow alongside you.'
'Leadership today isn't just about being visible — it's about being intentional,' added Crist. 'The women at this table don't just make room at the table. They build new ones. And they leave the blueprints behind for the next person to do the same.'
LOOKING AHEAD
As the conversation wrapped, panelists were asked what advice they'd offer their younger selves. Themes of boldness, setting boundaries, and curiosity came up:
'Go for the gusto,' said Laurie Jennings. 'Take that next job, even if you think you're not ready for it. Just go. Just push yourself.'
'Just say yes,' said Kerry-Ann Royes. 'Especially to try it all. If you fail, fail forward. I love being around women in development, real estate, construction - women doing complicated work to the betterment of society.'
'Never lose your curiosity,' said Vanessa Stabile. 'Ask a lot of questions, that leads to growth. Ask, learn, grow. That's how you're going to succeed and continue to move forward.'
'Be a litigator and negotiator,' added Kim Henderson. 'Ask 'what am I hearing, what am I seeing?' You don't need to prove yourself.'
'Take a chance,' said Dionna Hall. 'It can be a great learning opportunity to make you stronger.'
'It's OK to say no,' emphasized Sasha Seco Alvarez. 'Early in my career, I was asked to order lunch. I said, 'No — it's their turn.''