It’s a frigid night in January at Tilton School. Anyone who knows the cold winter wind on the Hill can attest that leaving the warmth of a dorm room to walk across campus on a night like this is a “by necessity only” situation. Yet, the Head of School House is packed for a totally optional event — the monthly birthday celebration hosted by Derek and Bobbi Krein.
“Even the coldest New Hampshire weather is no match for the warmth of our community,” says Mr. Krein.
Throughout the kitchen there is a dazzling array of homemade baked goods, crafted with care by none other than Mrs. Krein herself: confetti cupcakes and gluten-free brownies (always), tres leches cake, chocolate chip cookies, macarons, the list goes on. The Kreins have called the house their home for not quite a year and have been hosting these monthly birthday events only since the beginning of the 2024-25 school year, but the word is already out. Attendees include students and faculty celebrating their birthday — the Kreins are strident believers in the concept of a “birthday month” and took inspiration for the event from the traditions of their own family — as well as friends who are not celebrating a birthday but, rather, are excited about showing up for their roommates or teammates or, further still, just love any excuse to indulge in the now famous dessert lineup.
For the Kreins, these moments in the midst of the frenzied pace of a school year at Tilton represent something more than a simple birthday celebration.
“When we first met, we talked a lot about boarding schools,” says Mr. Krein. “Bobbi had been in admissions for a long time at that point, and she would always say to families who were in the process of searching for a school: ‘Make sure you ask who is going to say goodnight to your child.’ That’s perhaps the best test of what a boarding community is like.”
On this particular evening, the conversations that followed the dessert spread stretched on past check-in time (the students were excused, we promise) and the Kreins themselves were among those saying goodnight. As parents, it’s exactly the answer they’d want to receive to their question — knowing that adults at every level of the organization will care for their students.
“For almost our entire married life, we lived in dorms and were the family who had the door open even if we weren’t on duty,” recalls Mrs. Krein. “Now that we’re empty nesters who don’t live in a dorm, I just want to be around the kids. If you don’t like kids, you shouldn’t work in boarding schools.”
In that way, students, parents, and faculty alike recognize their authenticity.
Show up. Engage fully.
It’s not an accident that these four words became the credo of the Kreins’ first full year on campus.
“From the moment I arrived as a candidate for this opportunity, I felt a different kind of energy and enthusiasm,” says Mr. Krein. “That hasn’t waned a single bit. And I will say that, even on my busiest days, I feel like I’m the luckiest person going off to the work that I get to do with students, faculty, staff, parents, and alums.”
To understand the Kreins’ appreciation for the purpose and promise of independent schools, it helps to know how they got here. Mr. Krein, for instance, traces his calling to be an educator back to his early childhood.
“I think I was in education before I was in education,” he says. The youngest of three children, Mr. Krein’s older sister is developmentally delayed. He recalls the understanding, very early in his life, that she did not learn the way that he did and her challenges were much different than his own.
“I realized that every person will not do everything the same way, even if that’s how it is instructed to us,” he continues. “Think about swinging on a swing, how much goes into actually learning that skill, and trying to teach that skill to a sibling who doesn’t learn the same way you do.”
Immediately following his graduation from Connecticut College, Mr. Krein went to work at a boarding school. Over the next 30 years, he worked in nearly every capacity available to him at a boarding school: classroom faculty, coaching, residential life, college counseling, dean of faculty, etc. By the time he arrived at Tilton School, he’d been crafting his own vision — defined by a belief in caring for each student on an individual basis — for decades.
“It’s what I love most about Tilton’s history,” he says. “It has always been about the individual making progress, not simply moving a batch of kids along according to what a teacher wants. I think in many independent schools academic discipline can be the primary driver for faculty members. At Tilton, we care about adolescent development and having these teenagers emerge into the young adults that they need to be.”
“At our best,” he continues, “there is no better place for students and adults to learn than this environment right here.”
It’s also helpful to understand that the Kreins met at a boarding school. They’ve raised their family at boarding schools. They are all-in on this idea. Mrs. Krein, a self-described “public school kid,” remembers a simple conversation that started her on this path.
“When I went to college, my roommate was always getting phone calls that first year,” she recalls. “I finally asked her: ‘Who are all these adults you are getting calls from?’ It turns out that she went to a boarding school, and the calls were from her advisor, her dorm parent, her teachers — they all wanted to check in on her.”
Partially motivated by this exchange with her roommate, Mrs. Krein’s first job was at a boarding school. It pushed her out of her comfort zone, she says. She appreciated that. Eventually, her head of school asked if she might be interested in admissions work. She jumped into that opportunity as well, most recently as Director of Enrollment Management at Moses Brown School (RI). Mrs. Krein finds her experience to be a metaphor for the type of evolution that is possible for students.
“We take chances on people,” she says proudly. “And we’re forever evolving based on what students need and want to do.”
In a previous issue of The Compass, weeks after Mr. Krein started, he offered the following:
“Community is always a custom job. We’re going to create the next iteration of Tilton together.”
That is what the last year has been about: conversations with alumni, students, faculty, past parents, incoming parents, families who chose Tilton in the admissions process, families who chose to leave Tilton after enrolling. Every perspective, every anecdote, every piece of understanding has helped push the school forward.
“Tilton is a community that knows, supports, and challenges students to do really hard things, things that they didn’t know that they were capable of doing,” asserts Mr. Krein. “But the first part of that is knowing and supporting them.”
That is the ethos of Tilton School, and always has been, he says. The common thread — whether you talk to an alum from the 1960s or a current student — is students and parents who are supported by their own team of Tilton faculty members, helping to shape, individualize, and care for their experience on the Hill.
“I’ve worked at three Quaker boarding schools,” says Mrs. Krein, “and one of the things Quakers believe is that every person has a light within them. At Tilton, everything we do is about letting that light shine. Earlier this year, the entire faculty sat in a room and we discussed each student, one by one, to discuss their successes and their challenges everywhere, not just in the classroom.”
That is the heart of a Tilton education, more than the papers and speeches and exams and transcripts. As one alum puts it: “My schooling at Tilton was solid, but my education was outstanding.”
So, back at the Head of School House, single-digit temperatures outside, that 360 degree education is underway. Mr. Krein enthusiastically guides the students through a series of conversation cards. The students, though they’ll point to the dessert table and load their coat pockets with extras for late-night dorm snacks, are here for more than just the treats.
“The Kreins are the sweetest people on campus,” says Ella Makseyn-Santos ’26. “They’re welcoming and warm-hearted.”
While they appreciate that the students enjoy their company, the Kreins will simply tell you that this is a perfect match of people and place.
“This is a community that is not simply trying to be interesting,” says Mr. Krein. “Rather, our community is genuinely interested in other people. We are right where we want to be.”