Bill Benson’s Story: How a scholarship to Leadership Maine helped shape his leadership style and Boots2Roots, the organization he leads

Boots2Roots was born out of the challenges founder Dave Hickey faced in translating his 25-year Air Force career and advanced degrees into a compelling case for civilian employers in Maine. Once he overcame these hurdles and found his footing, Hickey resolved to assist others transitioning from active duty.  He found a willing industry partner in Bath Iron Works’ John Manganello. At first, he helped folks informally but soon realized the need for a broader solution and started Boots2Roots in 2016.  

In 2019, Bill Benson was hired as their first employee and began to build on the groundwork laid by Hickey and the board. Among the board members were Leadership Maine graduates Matt Harmon and Carrie Arsenault (Allagash), who believed that Benson would benefit greatly from the program. They anticipated that it would provide him with a comprehensive understanding of Maine’s economic landscape and valuable networking opportunities to enhance Boots2Roots’ efforts in matching veterans with suitable jobs that leveraged their skills and experience. 

However, as a new organization with a tight budget, affording the program was a significant challenge. Enter MDF’s Jan Kearce, who offered a Leadership Maine Scholarship. As Senior Program Director of MDF’s Leadership Programs, Kearce is dedicated to fostering diverse classes that represent a broad range of organizations. She notes, “Inclusion is at the heart of MDF and our leadership programs—cross-sector collaboration is crucial for creating a vibrant, prosperous economy and communities across Maine. Bill and Boots2Roots are making a positive impact, and I’m delighted to be part of his leadership journey.” Thanks to the scholarship, Benson joined the Damariscotta class of 2022-2023. 

Benson felt included from the beginning. Receiving the Leadership Maine Scholarship was validation that he and Boots2Roots were just as important as classmates coming from some of Maine’s most well-known companies. MDF saw value in the organization and invested in their participation. “I felt like I belonged,” Benson said of the experience.  

What has Benson valued the most from his Leadership Maine experience?  While he found the experiential learning expanded his understanding of Maine’s economy, challenges and opportunities, it’s the connections he made that have been transformational. He frequently encounters Damariscotta classmates at events across the state, has cultivated relationships with state government officials, and receives invitations to participate in new opportunities. These connections have also helped him in identifying future board members. Reflecting on his leadership, Benson shares, “I’m now more intentional about leveraging my team’s strengths and providing them with opportunities to utilize those strengths.” 

Boots2Roots has since expanded to a team of four staff members. They have successfully placed 310 veterans into 167 companies, not including the spouses and teenagers who have also found employment in Maine. For example, Benson’s own family—his wife as an emergency room nurse and his three children worked at Hannaford and Funtown Splashtown—embodies the broader impact of the organization. With many veterans relocating to Maine with their families, the total ripple effect of Boots2Roots is estimated to be close to 1,000 workers, most of whom have arrived in the past three years. The organization helps up to 10 veterans secure jobs in Maine each month. 

What’s next? Benson said he is budgeting to send another team member through Leadership Maine in 2025 to “double our connections!” His advice to others receiving a scholarship, “Feel like you belong, own it! There is a reason they are investing in you.”