2023 Monitor Icon: Miles Herman – Leading with a Drive for Growth and Change

by Brianna Wilson Sept/Oct 2023
Miles Herman, CEO of LEAF Commercial Capital, is best defined as a caring and encouraging leader who truly cares about his people and his clients, treating everyone around him like his own family. As this year’s Monitor Current Leader Icon, Herman shares his story of becoming the best leader he can be.

Miles Herman,
LEAF Commercial Capital

“[Miles] will go out of his way to make sure the people around him have everything they need to go as far in their careers as they want.” – Michelle Speranza, Chief Marketing Officer, LEAF

Before he began to consider a career in equipment finance, Miles Herman was heavily inspired by several people, including Sam Svetnick, the owner of a local pizza/steak sandwich shop as well as Al Benveneste, a Sunday school principal. Both were very talented at dealing with people when they were upset and related to their teams very well. From this humble start with personable, amazing leaders, Herman learned a lot about taking care of people in any job he had, from working in a local eatery to teaching Sunday school.

Herman carries these qualities with him today as CEO of LEAF Commercial Capital. He is dedicated to being a caring and understanding leader with his team and, equally, his clients. Having had many roles within the equipment finance industry, he’s had the opportunity to walk in the shoes of people he works with today. “I always try to remember what it was like to be in their shoes, when I was relatively young, coming out of school, or at a midpoint in my career and taking a chance to move from one department to another,” Herman says.

When he did enter the industry in the mid ‘80s, Herman got involved in building several companies, such as Master Lease/Tokai Financial Services, Fidelity Leasing (which became Citicorp Vendor Finance) and, most recently, LEAF Commercial Capital. In many of these ventures, he worked alongside Abe Bernstein and Crit DeMent, two men Herman considers amazing leaders who taught him about critical relationships and values.

“One thing that’s always stuck out about Miles over the decades we’ve worked together to start and grow the company is his tirelessness,” DeMent, who serves as the chairman of LEAF, says. “If there’s somewhere he knows the business needs to go, he just won’t stop until we get there. And the more he gets done, the more he seems to have the energy to do, which can be really humbling to anyone who tries to keep up with him. But with Miles, it’s never just pushing to move ahead at all costs. There’s a real humanity in Miles, a deep sense of the value and dignity of people. I think that’s always uppermost in his mind because when he pushes — and he will push — you can be confident that it’s only to the degree he knows you’re capable of, in pursuit of excellence he knows you’ll be proud of, even while you question your ability to stretch as far as he already knows you can.”

Startup Success

For Herman, the key to success is the willingness to work really hard and go the extra mile in multiple areas of business. He has watched LEAF grow from its foundation and notes that the highlight of his LEAF career, alongside working so closely with his clients and seeing them succeed, is seeing the people he met and hired when they were young get married, start families and even become grandparents.

“I’ve had the privilege of working with some of these folks for 20-plus years,” Herman says. He’s come to think of his team like his own family, even working with his brother Bob and sister-in-law Sheri for more than 30 years. “We exchange pictures at holidays, or we see what’s going on and when things are happening in their world and their lives that are meaningful. We’re all part of either celebrating or helping to give a shoulder to support them.”

Creating such a successful company wasn’t always easy. “As an independent finance company, capital and liquidity is your lifeline,” Herman says. “We had a period of time where we had to struggle to get to the finish line.”

During this time period, Herman and his team made sure they had enough money to make payroll and were able to sell some business and close credit lines that allowed the company to accomplish what it needed to accomplish. His team was surprised at everything they had achieved in a short period of time and tried to acknowledge Herman for it. “But I said, ‘It’s not just me; it’s the team. It’s what we’ve built and what we’ve tried to accomplish here,’” Herman says.

Investing in Young People

Herman truly enjoys seeing new talent join LEAF. He assists in recruiting out of college and has become invested in bringing people on board who don’t have experience as much as those who do so there is balance within the company.

Herman finds his experience with younger generations to be vital. He has learned equally from upper management, people who report to him and peers that operate on his level. This is one reason he tries to spend time with every new person who joins LEAF, whether he’s on the phone with them or able to meet them in person while traveling to different offices. His goal is to learn about new hires’ dreams, aspirations and goals, their interest in LEAF and their obstacles, if any.

“I took that approach because I remember, years ago, when I was still at Master Lease, I was there late one night trying to get something solved. Bruce Kropscot, the owner of the company came over and said, ‘Why are you working so late?’ Everybody else was gone. It was the year before we had all the HP 12Cs and computers, and I was trying to work on an add-on payment,” Herman says. “So, he sat there with me, and he showed me: ‘This is how you do it, this is how you use the add-on tables book,’ and we got it done in 10 minutes.”

Herman handles management today by walking around and checking in with his employees to see what they’re dealing with. He learns a lot just by sitting and talking to new hires, especially since a lot of what they run into doesn’t make it up to the top. This also has allowed LEAF to evolve its training and onboarding practices.

After all, Herman doesn’t add these younger people to his team just for them to agree with the higher-ups; he wants them to challenge his ideas and consider what’s missing, what’s different and what LEAF needs to engage upon that will make the company more successful.

“For me, one of the defining characteristics of Miles is his generosity as a leader and as a person,” Michelle Speranza, chief marketing officer of LEAF, says. “Having spent most of my career under his and Crit DeMent’s leadership, I’ve seen again and again how absolutely unstinting he is with his time, his encouragement, enthusiasm and expertise — which is extraordinarily deep. It’s clear he loves this industry and helping people grow within it. He will go out of his way to make sure the people around him have everything they need to go as far in their careers as they want, from a little on-the-spot guidance all the way to ongoing mentoring, something I’ve been fortunate to benefit from myself. He truly is a leader who puts his people first, believes serving customers is a privilege, and inspires everyone around him with his warmth, openness, sharp business sense and an incredible knack for seeing the opportunities to leap forward in the kinds of challenges that would cause other companies to lose ground.”

Continuous Growth

Herman has high hopes for the future of his team, his company and the industry. “We have witnessed much change at LEAF. We sold the company in mid-2017 to People’s United Bank (PUB) out of Connecticut,” Herman says. “Last year, PUB sold to M&T Bank and are looking at transformative elements to better enable us to serve our clients and customers. But it all begins with the people.”

Starting with the members of his amazing leadership team, who continue to help LEAF grow every day, Herman is excited to see each of them grow in their own roles and hopes they remain satisfied with the organization. He also hopes that LEAF, as a company, continues to effectively solve problems for its customers and vendors and lay the foundation for what those clients want to accomplish.

In terms of the industry’s future, Herman would like to see it become more diversified and be unafraid to embrace technology and change. He’s of the opinion that there are a lot of opportunities for other people to come to the table and really learn from the industry. LEAF, for example, visits universities and has a really strong internship program. “It’s been really rewarding,” Herman says. “It’s paying things forward to help the next generation really take the baton as we’re handing it off and help them to evolve and continue to grow.”

To the leaders of tomorrow, Herman imparts the following advice: Always ask why, ask how to get involved, follow through on commitments and don’t worry about getting things wrong. “I think about baseball,” Herman says. “You can get into the Hall of Fame with a .300 batting average; that’s basically one out of three hits. If we can do really well here and get better than that in our results, don’t worry about the mistakes that we make along the way. Those things happen. And if you miss the mark, you miss the mark, but at least you went down swinging and trying.”

ABOUT THE AUTHOR: Brianna Wilson is editor of Monitor. Rita E. Garwood, editor in chief, interviewed Miles Herman for this article.

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