"There were times when I called in like half the office to work on a proposal with me and they were all sitting in a room doing it. You just don't do that when you're a hundred people, right?"
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Ilan Cooper started at DT Global when the entire company was three to five people—two of them the co-owners. Sixteen years later, he’s Vice President of Business Development at a $450 million organization with 2,500 employees. That growth came in waves: organic growth from $5 million to $20 million, then a series of acquisitions that changed everything.
When DT Global was a small firm, Ilan ran business development and programs—about 60% of the home office staff reported to him, which meant seven or eight people. Job descriptions were “so broad you could drive a truck through them.” That was intentional. When a proposal needed to get done, he’d pull half the office into a room and they’d figure it out together.
“We were purely creative at that small size, right? Because there were very few processes. Everything was a new problem set. We made it up as we went, and we relied on our, our skills and our intelligence and our backgrounds, and just brought the best out of the eight, nine people you might have in the room to get somewhere.”
Then they bought a hundred-million-dollar company, and his team tripled overnight.
The management approach that had worked—what Ilan describes honestly as “winging it”—stopped working almost immediately. At the smaller firm, his team members were relatively homogeneous: young graduates with similar backgrounds and career trajectories. A one-size-fits-all approach worked fine. Suddenly he had people twice his age reporting to him, and the diversity demanded something different.
One of his hardest lessons was learning when not to help. Because he didn’t want to be overly hierarchical, he overcorrected and made himself too available. Someone would come to him with a question, he’d answer it—and inadvertently undermine whatever their actual manager was trying to develop in them.
” I feel like I knew most of the answers. I could just be helpful to anyone and I would just try and help them immediately. And actually sometimes that isn’t what your team needs of you, and whether it’s the right answer or not isn’t actually relevant.”
He had to learn to send people back to their managers, which didn’t come easily.
What did work was building intentionality into the structure. Weekly one-on-ones with every direct report. The first meeting of each month dedicated solely to career goals—not problem-solving, not answering questions, just development. He noticed that without that carve-out, meetings would devolve into answering questions, making decisions, and moving on. People got the answers they needed to do their jobs, but not the support they needed to grow.
The biggest shift was letting go of work he could do better himself. Before, if an assignment would take him under an hour and he knew he’d produce a stronger result than anyone on his team, he’d just do it. He had to unlearn that. His supervisor pushed him: not everything has to be at the best level it could be. Some things do, but many don’t. In those cases, let people stumble a little in service of their growth.
When asked what support he wishes he could give his managers, Ilan’s answer is immediate: time.
” I see a lot of my people in my team at stages of career that I was at five years ago, 10 years ago, whatever. And I really feel like if I had endless time, I could get them anywhere, but I don’t, right? And so more time I think would almost uniformly help every one of my direct reportees.”
He’s tried creating hypothetical proposal scenarios—real drafts in response to fake solicitations—so he could teach without the pressure of live deadlines. Almost every time, his people submit late. They push their own professional development below whatever the company needs that week. It’s just hard to make development take priority.
His advice for leaders at smaller organizations about to cross into mid-size: be careful what you wish for.
” You gotta be careful what you wish for, right? I don’t mean that in a bad or a good way. It’s just, people pursue growth for growth’s sake. Because the American dream, whatever it may be, right? But you all want to grow. You want to get bigger, and you wanna have that size and that whatever revenue, whatever it may be that you’re trying to grow. It changes things. ”
Don’t pursue growth without an intentional end state, he insists. Catalog what you might lose on the way there. Make sure the trade-offs are worth it. His boss, knowing everything he knows now, would make the same decisions. Ilan probably would too. But within three years of that first big acquisition, he and his boss were the only people left from the original small business. Nobody was fired. They all chose to leave.
The culture had changed. And that’s just what happens.