Not every manager or boss is a good one. Over my career, I’ve worked with many, and each was different. Some were exceptionally bright. Others embodied servant leadership. A few could rally teams toward a shared goal with dazzling precision. And then there were the terrible ones, the ones who led through fear, exuded arrogance, and saw their people as tools rather than humans. I’ve worked for them too, and it was hard.
But across my entire career, I never worked for a leader as large-hearted, kind, and empathy-driven as Doug Lebda. He was fiercely driven, sometimes exhaustingly so, but he led with true warmth and genuine care. And what was more, he was never afraid to show it. I didn’t work with him for long, but it was an incredible privilege. Even after I left LendingTree, he stayed present in meaningful ways, offering counsel, encouragement, and genuine support whenever I needed it.
In a world where leadership too often leans on fear, ego, and a lack of empathy, Doug stood apart. We lost someone important this week, not just to the LendingTree family, but to everyone who believes in entrepreneurship with heart and leadership that uplifts others. His wife, Megan, said it best:
“He was an amazing man with a heart so big it seemed to have room for everyone he met. Doug was compassionate, generous, and endlessly curious about the world and the people around him. He made friends everywhere he went. His energy was magnetic, his smile contagious, and his presence a source of comfort and inspiration.”
Doug’s passing is a reminder that leadership is not just about performance, scale, or strategy. It is also about the quality of the connection we create with those around us and the ones we influence. In an era obsessed with productivity metrics, AI dashboards, and growth, leaders like Doug remind us that empathy remains a true competitive advantage, and that drive and compassion can absolutely coexist.
The future of leadership will depend not only on how well we master artificial intelligence or in how we manage the complexity that the AI Era will bring us, but also in how deeply we understand people and take care of each other. Doug lived that truth instinctively. He showed that ambition and kindness can coexist, and that leading with heart does not make you soft, it makes you unforgettable.
Written in memory of Doug Lebda, whose example of leadership will continue to inspire many of us who had the privilege to know him.