In this post we recognize Derrick Cram, Business Manager for Business Services, for his 25 years of Service to Middlebury. He shares his what his first year at Middlebury was like, who had the biggest influence on his life, and what advice he would share with new employees, particularly in making connections with the great community of people at Middlebury College.
What job titles have you held while working here?
Golf Course Maintenance, Snowbowl Parking Lot Attendant, Snowbowl Lift Operator, Ski Shop Attendant, Ski Shop Technician, Ski Shop Lead, Ski Shop Manager, Ski Shop Manager, Golf Shop Manager, Golf Course Manager, and now Business Manager for Business Services
Take us back to your first year as an employee. What were the most significant things happening in your life outside of work at that point?
When I started my first year as an employee at Middlebury, two of the most significant things in my life up until that point were going to college and running my own business. I had been an entrepreneur and DJ from a young age, and I was used to wearing a lot of hats—booking gigs, managing logistics, marketing, and performing. That experience gave me a strong sense of independence, adaptability, and creative problem-solving, which I carried with me into my role at Middlebury. College had helped shape my worldview, but it was running my own business that really taught me how to work with people, manage time, and stay resilient in unpredictable situations. So when I joined Middlebury, I was excited to bring that same drive and creativity to a new environment—and to see how I could grow in a different kind of professional setting.
Have your interests/hobbies/athletic endeavors changed over the past 25 years? Have any of these been influenced by your work here or due to your association with others who work here?
I wouldn’t say my interests, hobbies, or athletic pursuits have changed during my time at Middlebury—rather, they’ve deepened. Middlebury has given me the space and support to explore them more fully and even intertwine them in meaningful ways. For example, I’ve been a DJ and entrepreneur from a young age, and Middlebury has not only encouraged that path but also supported it. The flexibility in my schedule has allowed me to attend regional, national, and international conferences, perform across the Northeast, and even tour in China. Several departments at the College have hired me over the years—whether as a DJ for Orientation or to provide a photo booth at receptions.
I’m also a passionate skier and a (somewhat mediocre) golfer—both sports that are often financially out of reach for many. Middlebury has created rare and valuable access to both industries, making them more affordable and approachable. Many of my ski and golf days have been spent with coworkers and acquaintances I’ve met through Middlebury, which has helped build a strong sense of community around these shared experiences.
Now that I’ve turned the page and begun a new chapter as part of a young family, I’m especially excited to share these experiences with my wife and kids. I’ve come to value skiing and golfing not just as personal passions, but as some of the best parts of living in Vermont—ways to make the most of winter, breathe in the fresh air, and take in the beauty of this incredible place we call home.
What is your fondest memory or experience that you’ve had while working at Middlebury?
This is a tough one—after being here so long, there are so many meaningful memories. But if I had to choose just one, I’d go back to my very first year as a staff member working at the golf course. That summer, there were three father-and-son pairs on staff: my father and me, John Rubright and his son Trevor, and Peter Burton and his son Ian. It was a long, hot summer, and I truly believe it set the tone for my work ethic moving forward. I didn’t want to let my father down, and that simple motivation pushed me to show up, work hard, and be reliable.
That summer was also filled with unforgettable laughs and stories—especially from the rich and colorful history of Middlebury’s golf and ski operations (most of which you won’t find in any official write-up). What made it so special, though, was having the chance to work side by side with my dad. At the end of the season, he told me how proud he was of my dedication and dependability, and that moment has stuck with me ever since.
Many people change jobs/careers multiple times in their working life. Something must have kept you here for 25 years. Is it anything that you can put into words?
You know, this is actually an easy one for me. Two things have kept me here for 25 years: a deep sense of dedication—and the people.
I come from a family that believes in sticking with what you start, supporting the work you do, and not turning away when things get tough. That mindset runs deep in my family’s history at Middlebury. My grandfather, Mahlon Cram, worked at the Snowbowl and Ralph Myhre Golf Course for 40 years, from 1951 to 1991. My father, Bernie Cram, followed in his footsteps and spent 33 years between the Snowbowl and the golf course before retiring in 2016. And I’ve proudly carried that torch—starting as a high schooler in 1998 and continuing ever since. Middlebury isn’t just where I work—it’s part of who I am.
But just as important as that legacy is the community that’s grown around it. The people here aren’t just coworkers—they’re family. That sense of connection is a huge part of what’s kept me grounded and inspired all these years. Whether it’s popping in to see Jen and Kara while grabbing the mail, catching up with Val about Bruce’s latest musical adventures, or chatting with Cathy and Emina about how my own family is doing—these small moments add up to something much bigger. I’ve had the joy of solving all the world’s problems with Curt, sending those inevitable SOS emails to Kris because someone hit the Kirk overhang (again), leaning on Joe at the Help Desk, pinging Rick James with Wi-Fi emergencies, and calling Phil at 4:40 p.m. on a Friday because a package is missing in action. I’ve had Scott help me out with AV on the weekend and asked the Communications team for last-minute help more times than I can count (and somehow they always pull through).
The list goes on—and that’s the point. This isn’t just a job. It’s a community that shows up, lifts each other up, and gets things done. Many of these people are still on campus, and many more are retirees I’m lucky enough to still keep in touch with. The depth of these relationships, the trust, the laughter, the support—it’s irreplaceable.
So yes, the legacy matters to me. But the people? That’s what’s made 25 years fly by.
What are your plans for the next 25 years?
Well, I’m only 43—there’s a good chance I’ve got another 25 years left in me! And honestly, as long as Middlebury continues to have a place for me, I hope to still be here. This place has been such a meaningful part of my life, both personally and professionally, and I’m excited to keep growing alongside it. Whether that means taking on new challenges, mentoring the next generation, or continuing to find creative ways to contribute—I’m all in.
Do you have a favorite place on campus?
There are a couple of spots—assuming the Snowbowl and Golf Course count as “part of campus.” One of my favorites is riding the Worth Mountain chairlift at the Snowbowl. As you crest the ridge and look out over Lake Pleiad and down into Hancock, it’s a fleeting but breathtaking view—made all the more special by how quickly it passes as the lift keeps moving.
Another favorite is just outside the golf course maintenance building, preferably on the old deck, with a cup of coffee in hand. Watching the sun rise over the Green Mountains, as the dew settles and the morning fog lifts off the fairways—there’s something incredibly peaceful about it. It’s one of those simple, grounding moments that reminds you how lucky we are to live and work in such a beautiful place.
Is there any person on campus (or retiree, former employer) that mentored you, or you feel helped you grow into your job, grow to enjoy your work and your time at Middlebury?
Honestly, there have been several people who’ve played a meaningful role in shaping my path at Middlebury. One of the first that comes to mind is Tom Corbin, my former manager and a now-retired member of the College community. Tom gave me some key opportunities early on that helped steer the course of my career. He also gave me a book called A Stake in the Outcome, along with some powerful philosophical insights into how he approached his work—ideas I still carry with me today and lean on regularly in my own role.
My father was another major influence. He taught me that dedication matters, and that a day of honest, hard work is a day well spent. John Rubright, simply by being himself, showed me that work can and should be fun—and that relationships are what really make the work worthwhile.
I also owe a lot to Peter Burton and Peter Mackey. Both of them gave me room to grow—not just professionally, but personally as well. They showed me that sometimes the best way to learn is to jump in, figure it out, and trust yourself in the process.
These mentors, among others, helped me not only enjoy my work, but also find meaning and pride in being part of this community.
If you could give one piece of advice to a new employee at Middlebury, what would it be?
Don’t just work at Middlebury—be a part of Middlebury. It’s more than just a paycheck. Make connections, join in, and take advantage of the community around you. Play in the employee golf tournament (even if you’ve never picked up a club—it’s often more fun that way), grab a drink with coworkers after work, catch a hockey game, help park cars at graduation, or respond to that IT survey with a kind word. The more you invest in the people and the place, the more you’ll get back. When you truly care about Middlebury and want to be part of something bigger, that’s when things start to click—and opportunities start to open.
Is there anything else that you would like to share about your time so far at Middlebury?
What stands out the most to me after all these years is just how deeply Middlebury is woven into the fabric of my life. Some of my earliest memories are from the Snowbowl, learning to ski when I was just four years old. My high school senior ball was held at the Snowbowl lodge. It’s been part of my life for as long as I can remember—well before I ever officially worked here.
Middlebury has always been more than just a job. It’s where I grew up, built relationships, found mentors, and now, where I get to share those same experiences with my own family. I’ve worn many different hats over the years, and each role has brought new challenges, lessons, and connections. I’ve watched this place evolve and had the privilege of growing right alongside it.
I’m proud of the work I’ve done here, grateful for the people who’ve shaped my journey, and excited to keep contributing to a place that’s been such a meaningful part of my life—professionally, personally, and generationally.