Every year, Vision Hudson Valley awards a recipient with the Ottaway Medal during its annual dinner, commemorating individuals devoted to serving Orange County and contributing to their local communities. For its latest ceremony on May 2, the group made several withdrawals from the bank and opened a checking account in preparation for its 29th honoree: Derrik R. Wynkoop, president and CEO of Walden Savings Bank.

Wynkoop was born and raised in Shawangunk and moved to the Town of Montgomery with his wife in 1991. He graduated from Wallkill High School in 1983 and then from Marist College in 1987 and 1992, when he received his bachelor’s in business and master’s in marketing, respectively. Following his graduation, Wynkoop pursued community banking, an industry he considers engaging and personalized, especially compared to commercial banking.

“Community banking is unique because you work, play, and volunteer in the community,” he said. “It’s a localized community feel, and my 36-year banking career allowed me to do that and have the impact that I’ve been able to have.”

Wynkoop has worked for three financial institutions, including the Wallkill Federal Savings & Loan for 14 years and the Hudson Valley Credit Union for eight years. He joined Walden Savings Bank in 2011 and became the bank’s 14th president following the passing of David T. Cocks that same year. Since joining, Wynkoop tripled the bank’s assets from $300 million to $900 million.

“Our 13th president died tragically at the age of 53 from a heart attack, and a lot will know him because he was here for 31 years. It created an opening. I was recruited from Hudson Valley Credit Union because I was local,” he said. “I lived here (Montgomery) but I worked in Poughkeepsie, and this allowed me to come back to where I was raised. So serving here, I was able to carry on Dave’s legacy.”

Throughout his entire career, Wynkoop and his banks have helped thousands of clients reach their financial goals, providing loans and plans for buying cars, funding weddings, opening small businesses, and more. Beyond writing checks, he and Walden Savings’ 11 branches participate in various facets of their communities, including chamber councils, ribbon ceremonies, and volunteer programs. Last month, members from Walden Savings created Peep dioramas of their bank and a yoga studio for St. Andrew’s Episcopal Church’s annual diorama contest; the bank won second and third place in the business category.

“Part of the beauty of being mutual and being small is we can give back to the community. One of the ways we have this success is our people volunteer their time,” he explained. “We lead by example: if I’m going to make you be at the MS Walk, I’m going to be there with you. I’m not sitting in my ivory chair and say ‘Wouldn’t it be nice and just make Abby go and do all the work?’ We go with you.”

One of Wynkoop’s biggest challenges is maintaining Walden Savings’ growth, as the bank lacks the size and profit that its commercial competitors possess. His solution to this is high-tech and high-touch advancements, such as self-service kiosks, virtual tours, and chatbots. Wynkoop asserted that, while the bank’s human touch would never go away, these innovations would provide customers with fast and modern services.

“We have to further exploit technology, but it’s not at the demise of people. People are the key; if you come to Walden Savings, it’s because of the people,” he said, “I’m not going to eliminate anyone, but I want to figure out how to marry people with technology.”

During the summer, Wynkoop and his family escape to their home on Seneca Lake in Watkins Glen, where he unwinds away from work. He was also an adjunct professor at Marist College and Mount St. Mary College and hopes to continue teaching after he retires from banking.

“Teaching is a passion; I am speaking at a seminar tomorrow in Albany, I’m teaching a class on leadership. I am the keynote speaker,” he said, referring to the New York Bankers Association’s Leadership 360 conference. “I love teaching, educating, and helping mentor the next generation.”

For this year’s medal dinner, Vision Hudson Valley themed the ceremony after the game of Monopoly, giving attendants hundreds of “Derrik Dollars” and Wynkoop a custom game board decorated with organizations that he and Walden Savings work with. During his speech, Wynkoop focused on the medal’s namesake, Ruth and James Ottaway, discussing their contributions to the county and how he champions their values.

“My goal that night was to bring the Ottaways back to life and tie my connectivity to them, so I channeled who they were,” he said. “The quality of how they ran their business, the humility in being so humble and grateful, and the need for society to be successful. You need charitable individuals and you need charitable organizations like Walden Savings Bank.”

Over 300 people from across Orange County attended the ceremony and cheered for Wynkoop during his standing ovation, a testament to his influence on everyone he worked with over his 36-year career. He shook so many hands and spoke to so many people that night, he needed to take off from the bank the next day to recharge.

“The word was surreal. It was a ‘this is your life’ moment. I had people from Hudson Valley Credit Union that have not been there for 13 years, I’ve had people come that I hadn’t seen in 20 years. Everybody along my life and career journey was there,” he said, adding that he was a little sad for not having enough time to talk to everyone that night.