The Signal

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...

Chapters

(00:00:00) - Not every degree is worth the same
(00:00:44) - John Fees on Higher Education and the Future
(00:02:12) - Bill Sonneson: The Crossroads of Higher Ed
(00:06:53) - Grad Guard: Why It Shouldn't Be Expensive
(00:11:06) - Gradguard: The College Enrollment Process
(00:17:00) - Markel on Higher Ed Decision Design
(00:21:17) - Enrollment Cliff: The College Professions
(00:24:29) - Benefits of Brightguard for College Students
(00:27:07) - Have We Reached a Mission in Higher Ed?
(00:29:02) - Grad Guard: The One Risk Students Should Know

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:

LinkedIn                              

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

AI-C...

Chapters

(00:00:00) - To Prove You're Human, You Have to Stare Into
(00:00:46) - Jeff Wilser: The Curious Edge of AI
(00:02:02) - In the Elevator With AI's Legends
(00:04:08) - What's the Most Human Problem That AI Can't Help?
(00:08:12) - Jeff Dylan on When Will AI Give Us Free Money?
(00:13:09) - Matthew McConaughey: Take Control of Your Identity in AI
(00:15:15) - In the Elevator With AI: What's Useful?
(00:23:36) - The Importance of AI in Higher Ed
(00:27:27) - Using AI for AI's Sake
(00:30:17) - Jeff Bezos on the Need for Curiosity in AI Jobs
(00:32:30) - The Signal: Higher Ed Tech Insights

In this episode—the 100th recording of The Signal—host Jeff Dillon sits down with Wendy Wong, Director of Enterprise Support and Client Engagement at Florida Atlantic University, who has spent 24 years transforming IT from a back‑office function into a driver of student and employee experience. Wendy shares the story behind OwlOne (FAU's branded version of Nebula One), a no‑code AI agent platform that sits in FAU's Azure infrastructure, giving the university complete control while avoiding the security risks of public AI tools.

Wendy reveals the secret to driving adoption: don't ask users what they want—show them what's possible. She walked into offices with use cases tailored to their actual work (residency forms, graduation ceremonies) and even shared personal examples like planning a trip to Japan. She also explains why strong change management—communication, expectation-setting, and grassroots efforts—was the real driver of success, not the technology itself.

For any CIO, IT director, or campus leader trying to figure out where to start with AI, Wendy offers practical advice: don't buy an AI point solution that will be obsolete in 18 months, and don't chase hype. Build a foundational platform that can evolve.

 

Key Takeaways 

Build a Foundational Platform, Don't Buy a Point Solution: Wendy advises against purchasing a standalone AI tool that will be obsolete in 18 months. Instead, build or adopt a platform that can evolve with the technology and the institution's needs. 

Don't Ask Users What They Want—Show Them What's Possible: Most people suffer from "blank page syndrome." Wendy showed faculty and staff tailored use cases (organizing a graduation ceremony, filling out residency forms) rather than asking open-ended questions. This approach unlocked adoption. 

Normalize AI by Showing Personal Use Cases: Wendy shared how she used AI to plan travel to Japan and translate for her Spanish-speaking family. When users see AI as a life tool rather than just a "student cheating tool," their mindset shifts. 

Strong Change Management Is the Real Driver: Communication, expectation-setting, grassroots efforts, and meeting people where they are were more important than the technology itself. The Cloud Force Frontier Award for AI Advocacy recognized FAU's change management efforts, not just the tech. 

Adoption Comes from Making AI Approachable: Wendy avoided tech‑intimidating language and made AI feel accessible to non‑technical users. The result: a 50x increase in adoption and nearly one billion tokens processed. 

Look for Partners Who Bring Expertise, Not Just a Product: The best technology partners challenge you, offer honest feedback, and help you succeed even if it means recommending something that doesn't directly benefit them. 

Use the "How Are You Using AI?" Question as a Screening Tool: When evaluating partners, ask them how they use AI internally. If they can't give a compelling answer, they likely don't understand how to help you use it effectively. 

Start Small, Build Momentum, and Let Successes Scale: Wendy's approach was iterative—launch with a few early adopters, capture their wins, and use those stories to bring in the next wave of users. This grassroots approach built credibility and momentum organically. 

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

 

Find Wendy Won...

Chapters

(00:00:00) - How Microsoft's AI Agents Became Popular
(00:00:43) - The 100th Guest: Wendy Wong
(00:02:21) - What's Keeps You Motivated at Florida Atlantic?
(00:05:38) - What Do CIOs Need to Know to Drive a Mobile App
(00:07:04) - Unifying IT support, help desk, desktop support
(00:08:51) - FAU's No Code AI Agent Platform
(00:14:31) - The University of Cambridge's AI Frontier Work
(00:16:51) - Fau's AI Governance
(00:19:20) - How to Deploy a Complex IT System in Higher Ed
(00:23:00) - What separates a Technology Partner from a Liability?
(00:26:15) - Where AI and the Student Experience Intersect
(00:27:49) - The Signal: Higher Ed Tech News & Insights

What happens when an enrollment marketing agency that's been at it for 20 years looks back and realizes their biggest lesson wasn't about campaigns—it was about finding the right partners?

In this episode, host Jeff Dillon sits down with Brian Hartnack, CEO of Archer Education, which just celebrated its 20th anniversary and was named Enrollment Management Solutions Provider of the Year. Brian shares the two founding principles that have guided Archer from day one: treat prospective students like the savvy consumers they are, and treat institutions as true partners focused on shared ROI.

Brian offers am illustration in the difference between traditional 18-year-old recruitment and adult learner enrollment—a distinction most agencies still get wrong. He explains why the brand that works for high school seniors doesn't carry the same weight with working adults, and why enrollment advising is a "litmus test" that tells students everything they need to know about what it will be like to be your student.

He also tackles the AI shift head-on, revealing that institutions have already lost at least 25% of organic referral traffic over the last two years. The game has moved beyond your domain—it's now about your entire web presence, including Reddit, TikTok, and earned media. And he offers a direct challenge to presidents and provosts: fund the data foundation, elevate your faculty, and create a shared vision that every corner of the organization actually wants to win.

 

Key Takeaways

Treat Students Like Savvy Consumers: You can't trick a prospective student into making one of the biggest decisions of their life. They want real answers to difficult questions. Meet them where they are.

Adult Learners Are Not High School Seniors: Traditional 18-year-old recruitment is about identity and belonging. Adult enrollment is an ROI purchase—career-driven, lonely, and beset by competing priorities. The same playbook doesn't work.

Brand Matters—But It Can't Overcome Everything: For adult learners, brand sits alongside tuition, flexibility, convenience, and responsiveness. A great name won't fix high prices, limited starts, or slow enrollment advising.

AI Has Already Reshaped the Funnel: Organic referral traffic is down at least 25% over the last two years. The student journey now happens in AI answers and chat before they ever reach your site. The game has moved beyond your domain.

Stop Treating SEO as Something That Lives Only on Your Domain: AI citations are assembled from your website, earned media, Reddit, reviews, YouTube, and social. Your goal is a robust, credible web presence across every node of the knowledge graph.

Data Interoperability Is the Foundation for AI: Everyone is shopping for AI solutions, but very few are laying the data foundation that makes AI useful. You need master data management—stitching your CRM, SIS, and LMS into one golden record. This is ongoing human work, not a one-time purchase.

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

 

Find Brian Hartnack:

LinkedIn                              

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

Archer Education

https://www.archeredu.com/

 

And find EdTech Connect here:

Web: https://edtechconnect.com/

 

Chapters

(00:00:00) - How to Gain an AI Cease
(00:00:34) - The Signal
(00:01:47) - Archer College Enrollment Management Solutions Provider
(00:04:21) - What Colleges Need to Know For Adult Enrollment
(00:08:22) - Top Higher Ed Executives: Brand Matters
(00:15:16) - Archer Innovation: Helping Colleges Build Internal Capacity
(00:18:29) - Building Internal Capacity for AI Search
(00:21:38) - Archer Education Partnerships: Red Flags
(00:26:29) - The Future of Enrollment: What Leaders Need to Know
(00:28:55) - Brian Archer on College Professions and the Future of Learning
(00:30:58) - The Signal: Higher Ed Tech Insights

What happens when a prospective student asks ChatGPT for the best computer science program in the Midwest—and gets a complete answer without ever clicking on your website? For higher ed marketers who've spent 15 years optimizing for clicks, that shift changes everything.

In this episode, host Jeff Dillon sits down with Andy Crestodina, co-founder and CMO of Orbit Media and author of Content Chemistry, to unpack what AI search really means for colleges and universities. Andy, who has been doing SEO for 25 years and teaches digital marketing at Northwestern, argues that the SEO playbook isn't dead—it's just expanded. The new goal isn't ranking; it's being cited.

Andy explains why program pages need to be dramatically more detailed than they've ever been, why "conversation optimization" matters more than keyword optimization, and how a 30-word prompt from a nervous 17-year-old can completely change the game for a small school competing against a flagship. He shares practical, actionable methods: run synthetic prompts, audit where AI is training on your vertical, and fix your homepage (which AI crawls far more than any other page).

For anyone trying to make sense of a world where traffic is down but intent is up, this episode offers a clear, grounded perspective from one of the most trusted voices in digital marketing.

 

Key Takeaways 

The Goal Has Shifted from Clicks to Citations: AI search doesn't send visitors to your site—it synthesizes answers from across the web. Your goal is to be the source behind the answer, even if the user never clicks through. 

Prompts Are Much Longer Than Keywords: The average prompt is around 30 words, not two or three keywords. To win in AI search, your content must align with the detailed, real-life questions prospective students would ask an admissions counselor. 

AI Search Is SEO + Conversion Optimization Combined: You need both algorithmic visibility (SEO) and alignment with visitor psychology (CRO). The playbook has expanded—not been replaced. 

Homepages Matter More Than Ever: AI crawls your homepage far more than any other page. If your homepage is a branded tagline without substance, fix it. That's where AI is trying to learn about your institution right now. 

Run a Synthetic Persona Audit: Build a detailed persona of your ideal student, then run 25 synthetic prompts on behalf of that persona. Ask the AI to output its sources. Audit those sources to see where you're cited—and where you're missing. 

The AI Has No Appeals Process: There is no one at OpenAI, Google, or Anthropic who will respond to your request to be ranked higher. Your only leverage is the quality and depth of your content. 

Thought Leadership and Original Research Are the Antidote to AI-Generated Sameness: If AI can write it, don't publish it. The internet doesn't need more generic content. Prioritize original research, strong points of view, and collaborative content that AI can't replicate. 

Brand Still Short-Circuits the Funnel: Brand awareness and word of mouth still matter. Not all marketing is algorithm-based. Relationship marketing, brand positioning, and share of voice are blue ocean opportunities. 

Start at the Bottom of the Funnel: Before you worry about AI visibility, fix your program pages. Address the basics: deadlines, financial aid, concerns. If there's a leak in the bottom, nothing else helps. Benchmark conversion rates by URL and prioritize the lowest-performi...

Chapters

(00:00:00) - How AI Is Affecting Cloudflare's Content Marketing
(00:01:59) - Higher Ed Marketing: Where's Marketing Heading?
(00:09:22) - How to Win in an AI-First World
(00:10:02) - AI Search: How Will It Affect Marketing?
(00:17:44) - How to Get More Out of Your Homepage
(00:21:41) - The Tension Between Optimizing for AI and Human Content
(00:27:00) - AIs Will Build Custom Websites
(00:29:43) - The Signal: Higher Ed Tech Insights