A Beyond the Brief Marketing Conversation with Jeremy Thompson, Vice President of Communications & Marketing at College of the Holy Cross.
Q: Jeremy, let’s start with your background. What first pulled you into marketing, and how did that lead you to Holy Cross?
Jeremy: My path into marketing was actually through the arts. I studied theater as an undergraduate at Western Michigan University, fully expecting to become a high school drama teacher, and discovered arts administration could be a viable career path while I was there. That realization led me to a small but highly regarded arts administration master’s program at the University of Alabama, including, at the time, a 15-month residency at the Alabama Shakespeare Festival, where I moved from the stage to the business side and learned how marketing, development, and audience strategy can shape an institution’s future.
From there, I took a job doing marketing and fundraising for the theatre program at the University of Vermont, which opened the door into higher education more broadly. Since 2007, I’ve led marketing, communications, and public affairs for a range of institutions, public and private, large and small, enrollment-hungry and highly selective, ultimately landing at Holy Cross in 2022, where the mandate is to take an already strong institution and position it for a new era of visibility and demand.
Turning comms shops into growth engines
Q: A theme in your career is transforming “traditional comms shops” into strategic functions. What does that look like in practice?
Jeremy: Many higher ed communications offices are still treated as service centers, great at making brochures, running the website, or sending press releases, but largely reactive. What I’ve tried to do, whether at the Boston University School of Law or now at Holy Cross, is move marketing and communications into the room where business decisions are made, so the team helps shape institutional strategy rather than just decorate it.
That means marketing is part of the conversation about program mix, pricing and discounting, delivery models, and the total student experience, not just promotion. When marketing brings research, data, and a clear view of the market to those conversations, it stops being “spin” and becomes a substantive partner in driving outcomes like enrollment, philanthropy, and reputation.
Holy Cross, Jesuit identity, and market reality
Q: Holy Cross sits in a crowded, competitive market and leans into its Jesuit identity. How do you differentiate without becoming “just another Jesuit school”?
Jeremy: When you land on our site, you should immediately understand that we are a Jesuit, Catholic institution—that’s intentional. But our distinctiveness is that we are the only liberal arts college in the Jesuit network.
This enables us to focus on building a four-year residential experience for students seeking a life of meaning and purpose, not just a first job. They arrive without a declared major, discern their path over time, and graduate not only with marketable skills but with ethical habits of mind and the ability to wrestle with complex issues in community, exactly what a polarized democracy needs and what employers increasingly value.
Enrollment success amid demographic and financial headwinds
Q: You’ve had notable enrollment gains at Holy Cross even as the sector faces demographic and financial pressure. What changed?
Jeremy: A lot of credit goes to President Vincent Rougeau and our Vice President for Enrollment Management, Cornell LeSane, who both came in with a mandate to modernize recruitment and admission. Historically, Holy Cross relied heavily on an exceptionally loyal alumni base and word of mouth; the shift has been toward a much more intentional, data-informed enrollment strategy.
Over the past three years, our admission rate has moved from the mid-to-upper 40s down to around 17 or 18 percent, and our yield has climbed from the upper teens to as high as nearly 50 percent. At the same time, we’re navigating real headwinds: the demographic cliff reducing the number of high school graduates, rising price sensitivity, and families at all income levels negotiating aggressively on aid.
As a sector, elite colleges like Holy Cross have now reached a price point that roughly one in 100 American households can truly afford. This presents a particular challenge for an institution grounded in the Jesuit, Catholic tradition of serving the poor and powerless. This is why Holy Cross provides full-tuition scholarships to households earning less than $100,000 a year and returns approximately 40 cents of every tuition dollar to students and families as institutional financial aid — more than $85 million dollars last year alone — not including other forms of federal, state, or private support.
High-impact experiences, AI, and preparing for what’s next
Q: How are you thinking about the academic and student experience as expectations shift and AI accelerates change?
Jeremy: One core concept of the Jesuit tradition is cura personalis, or care for the whole person, which calls us to approach student formation with attention to mind, body, and spirit. There’s strong evidence that students who have at least one high-impact curricular and one high-impact co-curricular experience, like meaningful study abroad, hands-on lab work, or a substantial internship with real mentorship, are much more likely to report being happy and fulfilled later in life. Our goal is to ensure every Holy Cross student can access both of these experiences, regardless of financial background, and we’re actively working to remove any barriers that stand in the way.
At the same time, we can’t pretend the world our students are entering will look like the one we grew up in, so we’re investing in a proprietary, closed-suite AI environment available to faculty, staff, and all students, paired with instruction on practical and appropriate use. Our campus community is also engaged in long-term critical inquiry into five “grand challenges” facing our global society — ethical computing and humane technology, inequality, climate, democracy and pluralism, and peacebuilding. The idea is to bring the 500-year-old Jesuit intellectual tradition into direct conversation with the tools and dilemmas of the 21st century, so graduates are both technically aware, adaptable to change, and deeply grounded in humanistic and ethical reasoning.
Data, segmentation, and the future of digital marketing
Q: Looking ahead, what are you going to do differently in 2026, and what are you going to stop doing?
Jeremy: We’re leaning into much deeper segmentation and geodemographic modeling to build a clearer understanding of the market segments we convert most and least effectively across the entire enrollment funnel, from prospect to matriculation, and even through to graduation. That’s going to inform not just messaging and media, but also where we see opportunities to tune the experience, and I’m eager to explore similar approaches with our alumni and advancement teams from a philanthropic perspective.
On the other hand, I’m increasingly skeptical of the value of traditional paid search and PPC as AI-driven search experiences push paid and organic links further down the page and change how people discover information. The question is shifting from “How do we get more clicks to our site?” to “How do we ensure AI systems and next-generation search are accurately informed by our content and brand?”, which may mean reallocating dollars from classic PPC into content, structured data, and experiences that feed both human journeys and AI-mediated ones.
Advice, authenticity, and marketing’s seat at the table
Q: What guiding principles shape how you lead marketing, and what advice would you offer peers facing similar pressures?
Jeremy: One of the most important lessons for me has been to slow down and listen; marketers can be caricatured as glib or purely tactical, but deep listening is critical to earning trust and ensuring substance is at the heart of our marketing strategy. Closely tied to that is a commitment to authenticity, working only in places whose mission you believe in and telling their story in a way that might make someone take notice without ever crossing into spin.
I’d also say: insist that marketing be in the room when decisions are being made about product, price, place, and experience, not just promotion, and come armed with research and data rather than opinions. In a sector where the economic model is under real strain, and the ROI conversation is often reduced to first paychecks, marketers who can connect mission, market reality, and measurable outcomes have a responsibility to help their institutions rethink how they create value — for students, for communities, and for society at large.
Q: For those who would like to reach out and connect, where can they find you?
Jeremy: LinkedIn is great, and I’d be happy to connect.