When Alex Furlong left the US Army in 2013, wholesale insurance wasn’t on his radar. But a chance introduction – from a military mentor to a brokerage executive – sparked a conversation that stuck. “It really piqued my interest,” he said. “A lot of people don’t know about the wholesale space, but it seemed like a unique and interesting pathway.”
Furlong (pictured above) began his career as a casualty broker and now holds a senior leadership role in the sector. His military background, particularly in Special Operations Forces, continues to shape how he leads. “The principles of good leadership don’t change,” he said. “They just show up differently depending on the environment.”
Furlong pointed to two qualities he sees as universally essential: sound decision-making and the ability to inspire. “The military reinforces that great leaders make good decisions and inspire their people,” he said.
In insurance, decisions must be rooted in facts. “Emotions have to take a backseat. You focus on the facts, interpret them through experience, and act accordingly.” But inspiration, he added, requires a different set of skills – and often, more finesse. “Your team has to know you’ve been in their shoes. They need to feel heard, understood, and supported.”
Asked how military-style planning fits into a sector often seen as cautious, Furlong reframed the question. “People think the military makes fast decisions with limited information,” he said. “But those decisions are usually the result of prior contingency planning.”
The goal, he said, isn’t rigid planning – it’s adaptability. “The best teams plan for what could go wrong. That way, when something unexpected happens, they’re not scrambling. They’re activating a plan they’ve already discussed.”
This mindset applies directly to insurance. “If you build a culture that embraces contingency planning and clarity of purpose, your team can pivot quickly – because they already know where they’re headed.”
One of Furlong’s guiding principles comes from his time in Special Operations: “You can’t build competent forces after an emergency starts.”
The insurance equivalent, he said, is anticipating where the industry is moving. “You have to build capacity for what’s coming – not just for today’s challenges. That means hiring the right people, investing in the right tools, and always thinking two or three steps ahead.”
Crises, he added, are best met with action, not hesitation. “Inaction breeds fear. Action breeds confidence. Even if you don’t know the perfect next step, take one. More options will reveal themselves.”
Furlong invests significant time in developing initiative among junior team members, especially those without high-pressure experience. “Initiative comes from confidence – and confidence comes from experience and leadership,” he said. “You give people chances to tackle challenges, and you support them while they do it.”
But initiative, he stressed, needs direction. “Initiative without alignment can take you in the wrong direction,” he said. “That’s why strategic intent is so important.”
Drawing from military doctrine, Furlong outlined three pillars of strategic intent: an expanded purpose (“the broader why”), key tasks (“the things we must accomplish”), and a clear end-state (“what success looks like”). “When people understand those things, they don’t need constant oversight,” he said. “They know how to act in a way that moves the company forward.”
One of the biggest adjustments in Furlong’s transition to the private sector was how authority works. “In the military, you still have to lead with influence – but your rank carries weight. In the private sector, you can’t rely on a title,” he said. “You have to lead every day by how you engage, how you listen, and how you inspire.”
That shift, he noted, can trip up some veterans entering civilian roles. But for those who adapt, the payoff is clear. “If you can combine interpersonal skills with the discipline and planning from the military, you can be very effective in insurance.”
And for those building organizations? “Hire for character, teach initiative, and make the mission clear,” he said. “That’s how you get teams that are ready – for whatever comes next.”
