Early in her career, Margaret Guelzow wore high heels to work for one simple reason: she was often the only woman in the room – and usually the shortest.
In industries like real estate and technology, where leadership tables were not built with many women in mind, a few extra inches felt like protection. The heels weren’t about style. They were about presence. About feeling like she belonged.
Over time, something shifted.
The confidence she once borrowed from her shoes became something she built herself – through preparation, through hard conversations, through moments when she spoke up before she felt fully ready.
Eventually, she stopped wearing the heels. She didn’t need them anymore.
Choosing “Why Not Now?”
Margaret’s career has been defined less by dramatic leaps and more by hundreds of small acts of courage. Saying yes before she felt completely prepared. Raising her hand when the role felt slightly out of reach. Choosing to ask, “Why not now?” instead of waiting for permission.
That mindset has followed her into every chapter of her leadership journey – including her role today as Chief Client Officer at Cherre, a real estate data management and intelligence platform that helps some of the world’s largest investment managers and operators make more confident decisions with connected, trusted data.
At Cherre, Margaret leads the teams responsible for ensuring clients don’t just adopt technology – they build confidence in the decisions it enables.
But the lesson wasn’t learned in a boardroom.
Committing to the Jump
Margaret is also a trained skydiving instructor with more than 1,500 jumps on her resume. She has stood at the open door of an aircraft thousands of feet in the air – a place where hesitation has real consequences. Skydiving teaches discipline. You prepare. You check your gear. You read the wind. And when it’s time to jump, you commit.
Leadership, she discovered, isn’t that different.
You don’t jump blindly. You prepare relentlessly. And when the moment comes, you move.
In her work with global real estate organizations navigating digital transformation, that mindset matters. Change can feel like stepping into open air. Systems evolve. Expectations shift. Stakes rise. But preparation, clarity, and trust create stability – even in motion.
When Speed Meets Connection
One of Margaret’s most important realizations didn’t come from a win – it came from friction.
Earlier in her career, she was relentlessly action-oriented. A “get it done” operator. But she underestimated something critical: relationships are not a byproduct of the work. They are the work.
“When people feel comfortable with you, they share more,” she says. “And when they share more, you can actually help.”
That shift – from speed to connection – reshaped her leadership style. It also deepened her impact.
At Cherre, that philosophy shows up in how her teams engage: not as vendors, but as long-term partners. Trust is treated as infrastructure – something that must be intentionally built, strengthened, and protected. Because in both client relationships and leadership, trust is what enables speed.
The Room Changes Anyway
Margaret built her career in rooms that didn’t always reflect her. She learned to navigate industries where women in senior leadership were rare. But rather than waiting for the room to change, she focused on changing how she showed up inside it.
Not louder.
Not harder.
Just steadier.
Today, when she walks into a room, the energy shifts – not because of volume or title, but because of preparation and presence.
On International Women’s Day, her advice to women earlier in their careers is simple: Stop waiting to feel completely ready. Say the thing. Raise your hand. Take the jump. The courage is rarely in one dramatic moment. It’s in choosing – over and over again – not to shrink. Eventually, you realize something powerful: You were tall enough all along.
