The Signal

Latest Episodes:

Ep. 110 - Eytan Wurman: Scouting Infrastructure for Artistic Intelligence Oct 23, 2026

Show notes

Jeff Dillon welcomes back Eytan Wurman, founder and CEO of CommonTime Pathways—the recruiting platform built on a simple, disruptive idea: creatives deserve the same recruiting pipelines athletes get. When Eytan and Jeff first talked about a year ago, CommonTime was just getting off the ground. Since then, the company raised $1 million from Yamaha and Reach Capital, expanded beyond music into theater and dance, and took the platform to the international stage at the ISME World Conference.

Eytan shares the big realization that reshaped CommonTime's mission: they weren't just helping music kids connect with scholarships—they were repositioning the artist as the center of an AI‑enabled future. He explains why music faculty are the most underutilized recruiters on campus, why they're already visiting high schools and adjudicating festivals, and why Common Time simply makes them 20 times more effective.

He also offers a brilliant analogy for two‑sided marketplaces: they're like middle school dances. Everyone's on the wall, no one wants to touch each other. CommonTime created the dance floor, set up the DJ booth, and then had to figure out how to get people to dance. The answer? The snowball dance. Get one college and one kid to talk, then another, then another—until everyone sees it's safe to join in.

For anyone thinking about enrollment innovation, creative talent, or what higher ed looks like in 2050, this episode is a must‑listen.

Key Takeaways

Artists Deserve the Same Recruiting Infrastructure as Athletes: Common Time is an athletics‑style recruiting platform for creative humans—musicians, and now theater and dance students. Colleges can find 13‑year‑old violists, oboists, and tenors the same way they find soccer players.
Music Faculty Are the Most Underutilized Recruiters on Campus: Music professors already visit high schools, adjudicate festivals, give lessons at summer camps, and build pipelines. Common Time makes them 20 times more effective by connecting them with non‑majors who want to keep playing in college.
Creative Students Are the Center of the AI‑Enabled Economy: The Forbes/LinkedIn versatility data shows that English and performing arts majors are among the most versatile degrees. As AI handles more technical production work, the ability to perform, present, communicate, and curate experiences becomes more valuable, not less.
The Unintended Consequence: Parents Are Talking About Music Like Sports: Students are telling their parents they want to study music earlier—and they're using Common Time to convince them it's viable. Parents are starting to see music as something that might pay for college, not just something that's good for you.
Application Pledges Change the Conversation: Colleges can now offer application fee waivers, audition waivers, and pre‑assigned scholarships tied to a student's profile—sometimes two years before they apply. It's the same model as athletics recruiting, and it signals early interest that changes how families see a school.
The Enrollment Cliff Is Creating Urgency—and Opportunity: With three million fewer college kids expected over the next five years and $75 billion in lost tuition revenue at stake, colleges are grasping for new ways to enroll students. Common Time opens the door to 10 million creative kids in the US alone.
Two‑Sided Marketplaces Are Like Middle School Dances: Everyone's on the wall, no one wants to touch each other. The hardest part is getting people in the door. Common Time created the dance floor, put up the DJ booth, and then ran the snowball dance—one college and one kid at a time until everyone joins in.
Common Time's Vision for 2050: To be the central hub where humans position themselves at the center of an AI‑enabled economy—where the world is full of art, community, and interactions based on beauty and humanism. In a year, Eytan wants Common Time connecting people because of their humanity to college experiences, and connecting colleges to real humans who can still do real thinking.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Eytan Wurman:

https://www.linkedin.com/in/eytanwurman/

CommonTime Pathways

https://www.ctpathways.com/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 109 - Melanie Moran: AI Can Learn Your Voice, It Can't Manufacture It Oct 16, 2026

Show notes

In this episode, host Jeff Dillon welcomes Melanie Moran, Vice President and Senior Strategist at Mackey Strategies, who spent nearly two decades at Vanderbilt University—rising to Associate Vice Chancellor for University Relations—and recently completed an 18‑month stint as interim head of athletic communications. She's seen campus and athletics communications from every angle: as a writer, a strategist, a leader, and an outsider brought in to bridge two worlds.

Melanie shares what surprised her most about athletics communications: the sheer volume, the round‑the‑clock pace, the 17 sports, the live broadcasts, and the massive, always‑on audience. She explains why operational separation makes sense—athletics needs to move fast—but why brand and strategy can never be siloed. The university's name is on the jerseys, and the best operations work hand in glove.

She also offers advice for crisis leadership. The best leaders don't panic. They create space to understand what really happened. They're willing to hear information they don't like. And they understand that trust is the currency of a crisis—the goal isn't to survive tomorrow's news cycle, it's to protect the institution's reputation for the next decade.

For anyone in communications, athletics, or institutional leadership trying to navigate an increasingly complex media landscape, this episode is essential listening.

Key Takeaways

Relationships Must Be Built Before the Crisis Hits: You don't want to be meeting your campus communications colleagues for the first time in the middle of a reputational fire. Establish regular check‑ins, track issues together, and know in advance who handles what.

The Crisis Playbook: What Happened, What Will We Do, What Will We Say: In that order. Don't skip ahead to messaging before you understand the facts and have decided on a course of action grounded in your values.

The Best Leaders Don't Panic: The leader's behavior sets the tone for the entire team. Calm creates space to understand what really happened and gives staff confidence that they'll be supported.

The Best Leaders Ask "What Do I Need to Know?" Not "How Do I Make This Go Away?" They're willing to hear tough news, even if it reveals a staff failure or a mistake that could have been avoided. You can't make good decisions without complete information.

Trust Is the Currency of a Crisis: Getting through tomorrow's news cycle is not the goal. Protecting the institution's reputation for the next five to ten years is. Trust and values are foundational—and they can be lost in the midst of a crisis if you're not careful.

AI Is Great for Getting Past the Blank Page—Not for Judgment: AI can synthesize information, test ideas, and handle repetitive work. But outsourcing judgment, leadership voice, or relationships to AI is risky. The question isn't "Is AI replacing communicators?" It's "How can AI free up communicators to think more strategically?"

The Transition from Individual Contributor to Leader Requires a Mindset Shift: Being the best writer or social media person won't prepare you to lead. You need to shift from "What can I produce?" to "What is the strategy behind it?" Learn the business of the institution. Understand what the president, provost, and athletic director are trying to accomplish. Invest in relationships before you need them.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Melanie Moran:

https://www.linkedin.com/in/melaniemoran/

Mackey Strategies

https://mackeystrategies.com/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 108 - Austin Blair: Buy-In Is Too Small of a Goal Oct 09, 2026

Show notes

What if the reason your enrollment strategy keeps stalling has nothing to do with the plan—and everything to do with the culture?

In this episode, host Jeff Dillon sits down with Austin Blair, Dean of Admissions and Marketing for both St. Francis Medical Center College of Nursing and St. Anthony College of Nursing, part of OSF Healthcare. Austin also coaches high school football, and that experience shapes everything about how he leads. He draws a direct line between coaching a team and building an enrollment operation: both are about creating belief, creating the experience before results, and understanding that talent rarely overcomes a bad culture.

Austin shares the story of uniting two distinct nursing college cultures—one in Rockford, one in Peoria, two and a half hours apart—with different histories, different demographics, and different ways of doing things. He explains why "buy‑in" is too small of a goal and why shared ownership is the real objective. He walks through his CULTURE framework: clarify the why, understand the terrain, listen before launching, turn committees into coalitions, use data as a mirror, reinforce through relationships, and empower shared ownership.

He also makes a provocative case against buying prospect names—a strategy he abandoned not out of philosophy, but out of necessity when his marketing budget was only $40,000. What he discovered was that relevance beats volume, and relationships beat lists.

For any enrollment leader, president, or marketing team trying to move a stalled strategy forward, this episode offers a practical, football‑tested framework for putting culture first.

Key Takeaways

Culture Before Strategy: Strategy tells people what you're going to do. Culture determines whether they'll actually get there. Enrollment problems rarely stem from enrollment challenges—they're usually cultural, communication, or trust issues.
Buy In Is Too Small a Goal—Build Shared Ownership: Buy in means the decision has already been made and you're trying to get people to agree. Shared ownership means shaping the decision together. People support what they build.
Talent Rarely Overcomes a Bad Culture: Austin has seen great enrollment plans fail because the culture wasn't ready to support them. He's seen talented teams underperform because they weren't aligned. Culture is the foundation.
Don't Skip the Listening Phase: The listening phase often gets compressed when leaders are under pressure to move fast. That's where you find who your arrogant leaders are—they think they've already solved it.
Good Ideas Don't Spread Just Because They're Good: They spread because people trust who's behind them, understand the idea, and see themselves in it. A good idea without adoption is just a recommendation.
Small Colleges Win by Being Human: Don't imitate scale—maximize intimacy. Own your traditions, own your identity, and don't try to be something you're not. The world will try to hate on you if you're inauthentic.
The First Question to Ask When Enrollment Stalls: What's your culture? Who's your biggest leader? Are you embracing who you are? Culture determines whether you'll actually get where you're trying to go.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Austin Blair:

https://www.linkedin.com/in/austin-w-b-63a306a6/

OSF HealthCare

http://osfhealthcare.org/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 107 - Si Elliott: Change Your Shoes, Not Your Software Oct 02, 2026

Show notes

What if the biggest problem in higher ed marketing isn't technology, budget, or even strategy—but the fact that we assume students make rational decisions when they're actually driven by emotion, bias, and the simple need to feel like they belong?

In this episode, host Jeff Dillon welcomes Si Elliott, founder of Fabrics, a customer experience consultancy that applies behavioral science to how organizations design experiences and relationships. Si also runs Diversity, a creative agency in Nottingham, England, and guest lectures at three universities—including the Communication University of China. He brings a rare outside perspective to higher ed, challenging institutions to stop designing around the needs of the organization and start designing around the experience of the person.

He explains why the technology amplifies whatever process is already there—good or bad—and why "marketing is better with psychology." He also breaks down three behavioral biases that could change how enrollment teams communicate: the curse of knowledge, social proof, and peak-end rule. And he offers a simple but powerful challenge to any president or CIO: put on a pair of trainers and a hoodie, walk around campus anonymously, and just observe. Change your shoes.

Key Takeaways

Psychology Is Better Marketing: Marketing isn't just persuasion—it's understanding people so you can serve them better. The goal isn't to trick people into converting; it's to make it easier for them to make the best decision for themselves.

Assume Emotional Decisions, Not Rational Ones: A 17-year-old choosing a university isn't just weighing league tables and employment outcomes. They're asking: "Can I see myself fitting in here? Does this feel like a place for me?" That's hard to track in a CRM, but it's the real question.

Three Biases That Matter Most: The curse of knowledge (you know your institution too well to explain it clearly to others), social proof (students need evidence they'll belong), and peak-end rule (people judge an experience by its emotional peak and its final moment). Use these to redesign open days, communications, and touchpoints.

Technology Amplifies What's Already There: If the underlying process is broken, technology will make it broken faster. Before buying a new platform, ask: are we fixing a process problem, an ownership problem, or a human understanding problem?

Don't Confuse Efficiency with Experience: AI and automation can streamline operations, but they can also strip the warmth out of a relationship. If an airline's automated messages leave a stranded passenger with no human contact for 72 hours, the technology is working against the brand.

The Value of Toil: Learning happens when you work through a problem yourself. AI shortcuts can rob students of the struggle that leads to true understanding. The future of education isn't competing with AI on processing—it's competing on context, nuance, creativity, and the human touch.

Map the Journey, Find the Friction: A customer experience audit starts with mapping the full journey—exploration, open days, offers, registration, student life—and identifying moments of high emotion or high friction. That's where you focus your attention.

Change Your Shoes: If you're a president, CIO, or marketing leader, put on a pair of trainers, jeans, and a hoodie. Walk around campus anonymously. Attend an open day. Buy a student a coffee and just listen. Observe body language in the corridors. Feel what they feel. That's where real improvement begins.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Si Elliott:

https://www.linkedin.com/in/si-elliott/

Fabricx

https://fabricx.agency/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 106 - Jeffrey Stepakoff: Content Is What You Put in a Sofa Sep 25, 2026

Show notes

What happens when a veteran TV writer—whose credits include The Wonder Years, Dawson's Creek, and Disney's Tarzan—decides to build a film school inside North America's largest soundstage complex? You get a model that challenges nearly every assumption higher ed has about where learning happens, who should teach it, and what students actually need to succeed.

In this episode, host Jeff Dillon sits down with Jeffrey Stepakoff, founder of the Georgia Film Academy and now President and co-founder of the Trilith Institute. Jeffrey has spent 40 years in entertainment, has over 1 million books in print, and has built two groundbreaking programs that bridge the gap between academia and industry. The Georgia Film Academy grew to serve 2,500 students a year across 30 institutions, helping grow Georgia's film production spending from $2 billion to $4.4 billion during his tenure.

Now at Trilith, Jeffrey is taking the model further—launching "Semester at Trilith," a 15-week, 15-credit immersive program that drops students into a working studio environment. He argues that in an era of AI abundance, the most valuable thing we can teach isn't craft—it's taste, critical thinking, and the ability to discern what stories actually deserve to be told.

For anyone in higher ed wrestling with questions of workforce relevance, industry partnerships, or the future of experiential learning, this episode offers a bold, practical, and deeply human vision.

Key Takeaways

Partnership Is the Engine of Success: The Georgia Film Academy succeeded because it brought together labor unions, state leadership, production studios, and 30 higher education institutions—including universities, technical colleges, and private schools—all aligned around a shared goal.

Credit Portability Is a Political Problem, Not a Technical One: The mechanics of transferring credits are doable. The challenge is institutional anxiety about losing students and resources. The solution is a consortium model with an R1 institution (like Clemson) serving as the accrediting body—similar to a semester-at-sea model.

Own Less, Access More: Institutions shouldn't be building their own soundstages or buying equipment that will be obsolete in 18 months. The future is about buying access to industry infrastructure, not owning it. Trilith partners with a 34-soundstage complex so students train on professional equipment in a professional environment.

In an Age of Abundance, Taste and Curation Are the Valuable Skills: AI can generate endless content. The scarce skill is knowing what deserves to be made—developing taste, critical thinking, and the ability to discern what stories matter and why.

What Do You Have to Say? Craft can be taught in a weekend. The deeper question is: who are you as a person? What stories are only you equipped to tell? That's what educators should be spending their time on.

The Goal Is to Build a New Creative Hub, Not Just a Factory: Georgia grew its production infrastructure to serve Hollywood. But the real opportunity is to build a self-sustaining industry based on original intellectual property—where writers, directors, and creators live, work, and tell stories that originate in the region.

Economic Impact Requires Measurable Metrics: To convince legislators and policymakers, programs must track outcomes—credit hours, job placements, industry spend. Accountability builds credibility and long-term investment.

The Future of Higher Ed Is About Partnership, Not Replacement: Jeffrey isn't trying to replace universities. He's building a model where industry and academia work together—each bringing what the other lacks—to create experiential learning opportunities that neither could deliver alone.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Jeffrey Stepakoff:

https://www.linkedin.com/in/jeffreystepakoff/

Trilith Institute

https://trilithinstitute.org/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 105 -Michael Leggs: The Essay Was Never Evidence of Thinking Sep 18, 2026

Show notes

What if the real crisis AI has exposed in higher education isn't student dishonesty, but the fact that we've been treating final papers as evidence of thinking—when AI can now simulate that thinking in seconds?

In this episode, host Jeff Dillon sits down with Michael Leggs, who has taught English at St. Paul College for 21 years and is the founder of Smartlby, an AI‑powered revision tutor designed to help students strengthen their writing through guided reflection—without writing for them. Michael brings a rare perspective: he's not a technologist or an administrator talking about AI in the abstract. He's the person reading the papers, watching students struggle, and redesigning assignments in real time.

Michael argues that detection software is a triage response, not a long‑term solution. The deeper problem is that our curriculum and assessment models were already fragile—AI just made it visible. He explains why surveillance tools create environments of mistrust, why revision should be treated as evidence of thinking, and how tools like Smartlby can guide students through a Socratic dialogue about their own writing without ever rewriting a single sentence.

For any faculty member, department chair, or academic leader trying to figure out what actually works in the AI era, this episode offers a grounded, practical, and deeply human perspective.

Key Takeaways

The Real Problem Isn't Cheating—It's Assessment Design: AI didn't create the problem; it exposed a weakness that was already there. We've been treating final papers as evidence of thinking, but AI can now simulate that product. The solution isn't more surveillance—it's redesigning how we assess learning.

Detection Software Is a Triage Response, Not a Solution: Institutions rushed to buy detection tools because it was something they could control. But surveillance creates environments of mistrust—students know we don't trust them, and that damages the learning relationship.

Revision Is Evidence of Thinking: The shift needs to be from product assessment to process assessment. When a student revises, they are thinking. Tools that track revision give instructors visible evidence of that thinking process.

Process Assessment Is Instructionally Scalable—Not Just Technically Scalable: Many tools are technically scalable (they work at scale) but not instructionally scalable (they don't actually help teachers teach better). Smartlby was designed by a teacher with 21 years of classroom experience, so it solves problems faculty actually face.

AI Closes the Production Gap—But the Learning Gap Is Still Open: Students can produce more effectively with AI assistance. But producing more isn't the same as learning more. The goal should be to close the learning gap, not just the production gap.

Redesign Starts at the Grassroots Level: Faculty sharing ideas about how they're redesigning assignments is where real change begins. It doesn't have to be a top‑down mandate. Department‑level collaboration on assignment types can create scalable, shared solutions.

Surveillance Tools Should Be Abolished in Five Years: Michael's hope is that within five years, institutions will stop policing student writing and instead focus on ethical AI use, assistive tools, and redesigning assignments that actually teach students how to think—not just how to produce.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Michael Leggs:

https://www.linkedin.com/in/mikeleggs/

Smartleby

https://smartleby.com/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 104 - Raffi DerSimonian: Ikigai and purpose driven paths Sep 11, 2026

Show notes

Jeff talks to Raffi DerSimonian, VP and Chief Strategy Officer at ERI, a digital agency that has been building for colleges and universities since 2005. Raffi came up on the institutional side—alumni relations at Becker College, then marketing and communications at Maine College of Art—before moving to the agency side. He brings a rare combination: deep empathy for campus dynamics and a strategist's eye for what actually moves the needle.

Raffi shares the story behind ikiGuide.ai, a tool that takes the Japanese concept of Ikigai—the intersection of what you love, what you're good at, what the world needs, and what you can be paid for—and turns it into a guided college search experience. Instead of handing a student a list of programs, ikiGuide gives them a path and the reasoning behind it, pulling in not just curricular offerings but also clubs, activities, study abroad, and stories of students and alumni who have walked similar paths.

The conversation also tackles the shifting role of the college website in an AI-driven discovery landscape. Raffi argues that with nearly half of prospective students now consulting AI before visiting a website, the site's purpose is no longer to provide facts—it's to provide a "vibe check," a sense of connection, and evidence that a student can see themselves there. He also offers a sobering challenge to institutions: if your differentiators sound like they could apply to any school in America, it's time to go back to the drawing board.

Key Takeaways

Start with Purpose, Not a Major: The traditional college search process begins with "what do you want to study?"—a question many 17‑year‑olds can't answer. ikiguide flips that by asking who you are, what brings you joy, and what you're good at, then connecting those answers to a full ecosystem of opportunities.

Only 30% of Gen Z Students Feel Prepared for Life After High School: According to Gallup and the Walton Family Foundation, the majority of students enter higher education without a clear sense of direction. Colleges have a responsibility to help them explore, not just funnel them into a predetermined path.

The College Website's Role Has Shifted from Facts to Vibe: With nearly half of prospective students now consulting AI before ever visiting a site, the website is no longer the primary source of information. Its job is to provide a sense of connection, evidence of differentiation, and a clear path forward—all within the first three seconds.

AI Is Moving the Discovery Upstream—But Websites Still Matter: Students are coming to websites already briefed by AI, with comparisons and assumptions already formed. The site needs to validate that they can see themselves there, not just repeat the facts they already know.

Personalization Requires Judiciousness: Over‑personalization can backfire if the institution can't fulfill the expectations it creates. The safer approach is to let users opt in to sharing their interests and then use that data to surface relevant opportunities—not to make assumptions about them.

Write for Both Humans and the Machines That Read for Them: AI is now summarizing institutions on behalf of students. Content needs to be findable for AI while still resonating with the human who will eventually read it. The line between the two is blurring rapidly.

Differentiation Is the Only Defense Against Sameness: Most higher ed websites look and feel identical. Institutions that clearly articulate what sets them apart—with evidence, not just claims—are the ones that win attention in a crowded market.

The Same Questions Colleges Ask Students Apply to the Institutions Themselves: Colleges should ask themselves: what is unique about our DNA? If your differentiators sound like they could apply to any school in America, it's time to dig deeper. Don't contort your value proposition to meet audiences where you think they are—lean into what makes you distinct.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Raffi DerSimonian:

https://www.linkedin.com/in/raffi-dersimonian-5099233/

ikiGuide

https://www.eridesignstudio.com/ikiguide/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 103 - Jenny Petty: The Alignment Gap That's Bankrupting Higher Ed Marketing Sep 04, 2026

Show notes

Jeff Dillon talks to Jenny Petty, Vice President of Industry Relations and Advisory Services at Simpson Scarborough, who has spent over a decade inside higher ed—most recently as VP of Marketing Communications at the University of Montana, where she helped reverse a decade‑long enrollment decline. Jenny brings a rare combination of private‑sector marketing experience (including growing a Facebook community from under 200 to over 1 million at IGT, working with brands like Dolly Parton and Family Guy) and deep institutional knowledge.

Jenny doesn't hold back. She argues that many CMOs are operating from fear disguised as prudence—dressing up inaction as "getting more buy‑in" or "the campus isn't ready." She challenges the instinct to centralize everything when things feel chaotic, warning that org chart changes often mask deeper alignment problems. She introduces the concept of "alignment debt"—the organizational equivalent of technical debt—that compounds quietly until it becomes one of the most expensive problems an institution faces.

For anyone leading marketing, enrollment, or institutional strategy, this episode offers both a diagnosis of what's broken and a framework—assess, align, activate—for actually fixing it.

Key Takeaways

Fear Disguised as Prudence Is Holding Marketing Back: Many CMOs are afraid—afraid of exposure, afraid of making a public mistake. That fear gets dressed up as "getting more buy‑in" or "socializing the idea more." The result is inaction. The institutions that need to change most are the ones that can least afford to wait.
Alignment Debt Is the New Technical Debt: Just like technical debt, unresolved misalignment in people, processes, and decision rights compounds quietly until it becomes one of the most expensive problems an institution faces. It shows up in missed enrollment goals, budget crises, and systems that break at the worst possible moment.
The Scope of the CMO Role Has Become Unmanageable: Job descriptions for higher ed CMOs read like seven jobs in one—crisis communicator, media relations, digital transformation lead, enrollment partner, and more. Marketing can't fix problems with the academic portfolio, pricing, or leadership misalignment. That's not a marketing problem—it's an institutional problem.
Political Savvy Is Necessary—But It Can Become Self‑Protection: You have to be political in these jobs. But the moment political maneuvering starts protecting your own position instead of serving the mission, it stops being leadership. Know your warning signs. Ask yourself: "Am I building healthy coalition, or am I being manipulative?"
Assess, Align, Activate Is a Flywheel, Not a One‑Time Process: The activation stage exposes false agreement. It reveals even more misalignment that you would have missed if you skipped from assessment straight to activation. Continuous improvement requires cycling through all three stages repeatedly.
AI Is Moving Production Work Upstream—Design Around That: AI is making production cheaper and faster. The question isn't whether to use AI tools—it's what humans should be doing when production is no longer the constraint. Judgment, synthesis, creativity, institutional knowledge, and relationship‑building are all moving upstream.
Managing Decline Is Not Stability: Growth, stasis, and managed decline are all strategies. But many campuses act like they're in a growth strategy while actually managing decline—and the misalignment shows up in budget, resources, and morale. Marketing leaders need to be at the table helping to resolve institutional contradictions, not just communicating outcomes after decisions are made.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find John Fees:

https://www.linkedin.com/in/johntfees/

GradGuard

https://gradguard.com/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 102 - John Fees: The Insurance Founder Who Says His Own Company Shouldn't Have to Exist Aug 28, 2026

Show notes

What if the best measure of an insurance company's success isn't how many claims it denies, but how many it pays—and how many of those students re-enroll?

In this episode, host Jeff Dillon sits down with John Fees, co-founder and CEO of GradGuard, a fintech company that has protected more than two million students across 750 colleges and universities. John brings a rare perspective: he's a founder who built his first company in higher ed in 1999, sold companies to Viacom and JP Morgan Chase, and has spent three decades at the intersection of education, finance, and technology.

But here's the thing: John believes GradGuard shouldn't have to exist. He argues that the cost of college has become unsustainable, and that the student loan default crisis isn't about over-borrowing—it's about students leaving school without graduating. Health issues, mental health crises, and other disruptions are the primary drivers, and most schools don't even track how many students leave for legitimate medical reasons.

John shares how GradGuard flipped the insurance industry's scoreboard—measuring success by claims paid rather than claims denied, and tracking re-enrollment rates (currently around 75%). He also introduces the concept of "decision design," explaining how universities shape student outcomes through choices families don't even realize they're making.

For any enrollment leader, CFO, or student affairs professional thinking about retention, student risk, and the financial realities families face, this episode offers a deeply human perspective on a problem hiding in plain sight.

Key Takeaways

GradGuard Shouldn't Have to Exist: John believes the cost of college is the root problem. If education were more affordable and schools were more generous with refunds, tuition insurance wouldn't be necessary. But the reality is that most families can't afford the financial loss of a disrupted semester.
Student Loan Default Is About Dropouts, Not Over-Borrowing: The real crisis isn't that students borrow too much—it's that they leave school without graduating. If you don't finish, you don't get the ROI. That's the problem GradGuard was built to address.
Health Issues Are the Premier Reason Students Leave: According to Lumina and Gallup studies, health issues—including mental health—are at the top of the list of reasons students don't persist. Mental health isn't a "disorder" to be treated differently than physical health; it's a legitimate reason for withdrawal.
GradGuard Measures Success by Claims Paid, Not Claims Denied: The insurance industry traditionally tracks profitability by denying claims. GradGuard flipped that model. The real measure of success is: did the student re-enroll? Currently, about 75% of students who file a claim return to the same school.
Decision Design Is Hiding in Plain Sight: Universities shape student outcomes through forced decisions—living on campus, meal plans, health insurance—that families don't always realize are choices. CFOs and enrollment leaders are decision architects. Helping families make informed decisions benefits everyone.
Trust Has to Come Before the Transaction: In higher ed, trust is everything. The objection GradGuard hears most is: "We don't want families to think about bad outcomes." But ignoring the risk doesn't make it go away. Transparency builds trust.
Tuition Insurance Is Affordable at Scale: When schools partner with GradGuard, the cost is around 1.2% of tuition—about $120 for $10,000 of coverage. Without a school partnership, it's twice as expensive. The spread of risk across a large pool makes it affordable.
Don't Go to School Without Protection: John's advice to families: know the school's refund policy. Don't assume a nonprofit will give your money back if something bad happens. Insurance isn't about expecting the worst—it's about being prepared so a setback doesn't derail a student's entire future.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find John Fees:

https://www.linkedin.com/in/johntfees/

GradGuard

https://gradguard.com/

And find EdTech Connect here:

Web: https://edtechconnect.com/

Ep. 101 - Jeff Wilser: How One Chatbot Cut Summer Melt in Half Aug 21, 2026

Show notes

In a world drowning in AI hype, how do you separate what's actually useful from what's just shiny? And what happens when the people building AI can't even agree on where it's going?

Jeff Dillon sits down with Jeff Wilser, a journalist-turned-AI-strategist who has written for The New York Times, Wired, and GQ, hosted the AI Curious podcast (named by Inc. as one of the best ways to get AI savvy), and spoken at Davos. Jeff brings a reporter's instinct for cutting through noise and a storyteller's ability to make complex topics clear.

Jeff shares his "Curiosity Canvas" framework—starting with a "drudgery dump" to identify the boring, repetitive tasks AI can automate, freeing up time for what actually matters: human connection, creativity, and strategic thinking. He argues that the biggest mistake organizations make is using AI to cut rather than to grow.

He also tackles the existential tension in higher ed, referencing a business school dean who sees AI as a threat to universities while simultaneously driving 90% faculty adoption inside his own building. The takeaway: don't bury your head in the sand. Use AI to be more competitive, not to replace what makes education human.

And for anyone worried about what skills matter in an AI-driven world, Jeff's answer is simple: double down on curiosity. The tools will change constantly, but curiosity never goes out of style.

Key Takeaways

AI Should Empower, Not Eliminate: The goal isn't to replace humans with AI. It's to automate the drudgery so people can spend more time on high-value work—mentoring, brainstorming, building relationships, and thinking strategically.

The "Drudgery Dump" Is Your Starting Point: Make a list of the most boring, repetitive tasks you do—the things you could do while watching Netflix. Those are the tasks most ripe for AI automation.

The IKEA Example Is a Blueprint: IKEA didn't lay off 8,500 customer service agents when it introduced an AI chatbot. It retrained them as interior design advisors and generated €1.3 billion in new revenue. That's empower, not eliminate.

AI Should Solve Problems, Not Be a Coat of Paint: Jeff shares a cautionary tale of a hockey team that slapped "AI Night" on the jumbotron and used Snapchat-like filters. Fans come to watch hockey, not AI gimmicks. In higher ed, don't brand your solutions as "AI" just to sound innovative—focus on the actual problem being solved.

Curiosity Is the One Skill AI Can't Replace: Jeff Bezos says the most important attribute for a CEO is curiosity. Tools will change constantly, but curiosity—the drive to ask questions, explore, and learn—will never go out of style.

Use AI for Growth, Not Just Efficiency: Too many leaders ask, "How can AI help us do what we're already doing faster?" The better question is: "What could we be doing now that we couldn't do before because we have AI?"

Start with a 90-Day Roadmap, Not a Slide Deck: Jeff's workshops don't end with inspiration—they end with a plan. Build an accountability team, set a two-week proof-of-life milestone, and focus on both low-hanging fruit and bolder agentic workflows. Treat AI like any other project, not a mystical magic wand.

The Signal Newsletter:
https://edtechconnect.com/newsletter

Find Jeff Wilser:

https://www.linkedin.com/in/jeffwilser/

AI-Curious Podcast

https://podcasts.apple.com/us/podcast/ai-curious-with-jeff-wilser/id1703130308

And find EdTech Connect here:

Web: https://edtechconnect.com/