As advancement professionals trying to re-engage alumni and encourage giving, we often face resistance rooted in their student experiences. We see our institutions as launching pads for lives and careers, but they may not see it the same way.

The bottom line is that if alumni don’t feel their alma mater gave them a potent professional springboard, their interest in giving back time, talent, and treasure simply won’t be there. And with AI changing the game of higher education so quickly, that tenuous connection risks breaking completely.

That’s why I found John Hill’s conversation on the first episode of our Speaking Engagement podcast so valuable. Hill, the vice president of story at Whop, has roots planted on both sides of the tech/higher education divide, so he has a unique view of how both industries can work together better.

“I think, with AI, the easy thing to do is to become fearful. The harder thing is to lean into it and actually see what it looks like,” Hill says. “[AI is] not as bad as I think people are viewing it, partly because they’re viewing it as, “is it going to cost my job’ instead of ‘is it going to change my life?’”

AI + Entrepreneurship: An essential toolkit for careers

Reshaping institutions to become stronger professional springboards in the age of AI requires fundamental shifts in the way they operate. Right now, Hill says, institutions are either encouraging students not to use AI, or they’re making decisions about student AI use in committees at a very high level, without student input.

“That’s a verticalization of who owns AI at an institution. You have to horizontalize AI,” he says. “It has to cut through every faculty, student, every administrator on campus. They have to have a general aptitude of it. You’re not going to survive unless you start to do that.”

At the same time, AI is forcing much of the job market to shift to a “maturation of the gig economy,” Hill says. In the not-so-near future, he adds, it’s very likely that just about everyone will be an entrepreneur on some level. “It’s no longer about finding the job, it’s about being the job.”

Colleges and universities, then, must expand entrepreneurship training out of the business school and into every major. Every student, no matter their preferred career path, must graduate with some level of entrepreneurial preparation.

How advancement fits into the equation

Much of this requires change at the academic strategy level—how will curriculums change? How will majors, departments, and even entire schools restructure?

But an equally critical question arises at the development level: How can we support this transformation through fundraising and engagement? A few of the ideas that popped into my mind as I listened to Hill speak are:

• Soliciting gifts for student seed funds: These would support students building their own businesses and products using tools like Whop while still in school.

• Creating “visiting professorships” for alumni entrepreneurs in residence: Business schools often do this, but with financial support, institutions could expand this resource to other schools and majors.

• Facilitating virtual micro-internships between students and alumni that give the former valuable experiences without leaving campus and the latter a meaningful connection back to their alma mater.

• Highlighting faculty, students, and alumni at all stages of the entrepreneurship process: Don’t just spotlight the big, splashy successes. In the magazine, on the website, and via social media, show how “being the job” can look for different career paths.

AI undeniably poses present and future risks for higher education, as well as for the wider economy. But these seismic changes also offer a great opportunity for colleges and universities to re-establish their role and relevance not only for students but for alumni, too.

“With the advent of AI, everyone is going to be moved into that entrepreneurial spot. It’s how much support they have around them that’s going to help these people out,” Hill says. “Figuring out how to develop lifelong engagement that’s meaningful to these people, those organizations will reap the rewards long-term.”

More content from Week 1

• This week’s learning guide

• Keynote: John Hill, VP Story at Whop

• From Ryan: Advancement can help alumni and student creators

• From Annie: Community Is the Product

• From Dave: When the Story You Tell About Alumni Stops Matching the One They’re Living

An entire economy has formed around human connection, and as engagement professionals, we need to start paying attention and learning from them.

Hampton is a paid peer community for startup founders. Members are vetted, placed into small core groups of about eight people, and meet with a facilitator roughly ten times a year. It also has a digital community where members can engage between sessions. The whole thing generates around $8 million in annual revenue.

Chief, a network for women executives that I belong to, runs on a similar model. It has curated small groups, structured conversation, and real community with both in-person and virtual options. In 2022, Chief reached the infamous “unicorn status,” hitting a $1.1 billion valuation in just three years.

Starting in Amsterdam and spreading across Europe, The Offline Club has created phone-free hangouts for strangers who want to unplug and connect IRL. Friendship apps (think Bumble BFF, Peanut, Timeleft, etc.) have collectively generated over $16 million in U.S. consumer spending in 2025 alone.

People are paying for structured ways to belong and be in community. That’s not a trend - it’s a societal correction.

In 2023, the Surgeon General declared loneliness a public health epidemic. Back in 1990, only 3% of Americans reported having no close friends outside of family. By 2021, that number had quadrupled to 12%. The private sector noticed before most of us did, and they built products around it. The design principles those products share are worth studying, because they’re the same ones that determine whether your engagement work succeeds or fails.

And here’s the part most engagement professionals in higher ed and nonprofits aren’t talking about yet: philanthropic behavior and consumer behavior are more alike than we want to admit. People give to organizations they feel genuinely connected to. They stay connected to things that fit their lives, their values, and their goals. The private sector has been studying what makes people feel that way for years. We should be reading those signals.

What the best communities are actually doing

The strongest community products share a set of design principles, and they’re worth naming because most engagement programs violate at least two of them by default: small groups, real structure, low barrier to entry, multiple modes of participation, and designing for the life people are actually living.

Small groups, not audiences or crowds. This isn’t about throwing a big tailgate or a gala. It’s about bringing three to ten people together where everyone is expected to participate and connect. You scale by growing the number of groups, not the size of them. The moment a group gets too big to go around the room, you’ve lost the thing that made it work.

Real structure. Prompts, facilitators, time limits, clear expectations. Nobody shows up wondering what they’re supposed to do. This is actually what makes participation feel safe enough to happen. An unstructured networking hour sounds friendly, but for most people it’s just anxiety with a name badge. Structure removes that friction.

Low barrier to entry. No board seat required. No event to plan, no year-long commitment to make. You show up, you participate, you leave. That simplicity is intentional. The easier it is to say yes the first time, the more likely someone comes back.

Multiple modes of participation. The strongest communities today offer both synchronous and asynchronous ways to engage. A live session anchors the experience, but there’s a way to stay connected between them. Chief does this well. [Advancement Talent Co.](your link here), the professional community I run for advancement talent professionals, does too. We meet virtually every month, and members can engage on our platform between sessions when they need it. Flexibility lowers the barrier to reentry, not just entry. And reentry is where most engagement programs fall apart.

Designing for the life people are actually living, not the version you assume they have. Peanut exists because someone noticed new mothers were isolated in a life stage nobody had built a community product for yet. The alumni newsletter I once helped produce included kids’ activity downloads because our alumni were parents with young children, and meeting them in that reality mattered. The best communities are built around who people actually are right now, not who they were when they graduated or when they joined.

Here’s where things diverge from how most engagement programs actually work.

Most organizations design engagement around output. Attendance. Clicks. Participation rates. We ask how many people showed up, not what it felt like to be there. In advancement, in nonprofits, in membership organizations, engagement often looks like a calendar. A series of events. Communications tied to moments in time. Those things aren’t wrong. But they don’t create connection on their own.

People don’t build relationships because you invited them to something. They build relationships because the environment made it easy to do so. There’s a difference between access and connection, and most organizations are still optimizing for access. More emails. More events. More touchpoints. But access doesn’t guarantee anything. You can give someone a dozen ways to interact and still not create a single meaningful relationship.

The communities growing right now, and charging for the privilege of joining them, aren’t winning because they have better content. There’s no shortage of content. They’re winning because the experience is better. Hampton isn’t selling information. Chief isn’t selling a network directory. They’re selling what it feels like to be in the room. To be with people who get it, who understand you — to not feel alone. Most engagement strategies are designed for reach. The ones that work are designed for belonging.

The design tension that kills engagement

There’s a failure mode on each end of the spectrum, and I’ve seen both up close.

The first is abdication. The institution hands the keys to a volunteer board without defining where the car should go. The board pursues pet projects, consumes enormous staff time, and produces activity disconnected from anything strategic. The members are engaged. The institution is not served.

The second is isolation. The institution designs everything internally, then wonders why participation falls flat. The community wasn’t included in building the thing they were supposed to care about.

The organizations getting community right sit somewhere in between. They design the structure — the format, the timing, the prompts, the purpose — and then invite people into it. They hold the frame. They don’t build inside it alone.

In our first Keynote conversation, John Hill described bringing stakeholders into the room to shape the product from the start. That instinct is exactly right. The best community designers know what they’re building and why, and they build it with the people they’re building it for.

What to do with this

The organizations building the strongest communities right now, startups and century-old institutions alike, are treating community as a core product. Designed. Intentional. Structured for small groups, flexible participation, and repeat engagement.

If your engagement strategy doesn’t have that at its center, you’re not behind the curve. You’re behind a market that already validated what works and is actively scaling it.

The question isn’t whether people want community. They’re already buying it. Ask yourself whether you’re building something worth joining, and whether you’re using the right principles to get there.

More content from Week 1

• This week’s learning guide

• Keynote: John Hill, VP Story at Whop

• From Ryan: Advancement can help alumni and student creators

• From Kristin: AI can enhance the student and alumni experience—but not in the way you think

• From Dave: When the Story You Tell About Alumni Stops Matching the One They’re Living

Most alumni surveys still ask some version of the same question: Where are you now?

Job title. Employer. Industry. City.

The data comes back clean. The picture it creates is incomplete.

John Hill made an observation in his conversation on the Speaking Engagement Keynote that I haven’t been able to set down. He was describing the perception problem at Whop - the platform he now leads community and story for - where the narrative the market had formed around the company had stopped tracking with what the platform was actually becoming. The early story: young, male, sneaker bots, college dropout energy. The actual reality: 160,000 companies generating revenue. Three med students running a membership business helping undergrads navigate the MCAT. A 19-year-old teaching other gamers to build maps and sell them. A traveling nurse aggregating jobs for other traveling nurses, generating $4,700 a month on a jobs board she would have been curating anyway.

The story people had about Whop was real. It just described a version of the thing that no longer existed.

Universities have the same problem with their alumni, and most haven’t noticed.

The institutional alumni story runs something like this: you came here, you grew, you graduated, you built a career. The credential opened doors. You succeeded. Now you give back. That story works for a portion of the alumni base. For a growing portion, it doesn’t land the way it used to - not because those alumni don’t value what the institution gave them, but because the path the story assumes no longer describes the life they’re actually living.

Hill has spoken at 249 universities in person. He’s watched the economic graph shift in real time, and he’s direct about what it means: “It’s no longer about finding a job. It’s about being the job.” Flex employment. Micro-networks. Digital businesses built from expertise most institutions wouldn’t have thought to credential. Alumni who are two years into freelance work, or three pivots into something they couldn’t have named at graduation, or building something that generates real income from an interest that never would have appeared on a career services intake form.

The “where are you now” question can’t hold them. And so the alumni story, the one institutions rehearse in magazines, at reunion weekends, in the opening line of every annual fund letter, quietly drifts from the story the alumni would tell about themselves.

That drift is not a communications problem. It’s an identity problem.

Engagement research keeps circling this without quite naming it. Alumni who feel like the institution’s story of success still fits their life show up. Alumni who feel like they’ve moved past the frame the institution offers tend not to. The activity data looks like apathy. Something closer to misalignment is underneath it.

The drift runs in two directions, and the second one is harder to see.

Institutions have moved increasingly toward telling stories about the student experience: what it feels like to be here, what the community offers, what the credential promises. That shift makes sense when outcomes are harder to guarantee.

But the alumni held up as proof of that experience are still largely the ones the old model produced.

If the only alumni a program is reaching are the ones the original story worked for, the institution is using a curated sample to validate a promise it may no longer be equipped to keep.

What is presented as evidence is often a version of the past, selected because it still fits the promise.

Hill was clear about what actually works in community building: bring the stakeholders into the room before deciding what to build. Not to pitch them, but to understand what they need. The communities that hold, he said, are the ones where the voices of the people you’re building for have actually shaped what gets built. Most alumni programs are designed in the opposite order.

The question worth sitting with, for any shop running re-engagement campaigns, reworking reunion programming, or rebuilding annual fund messaging, is a simple one: whose story are we telling?

If the answer is the institution’s story of what alumni should be, the next question is how far that story has drifted from the one alumni would write for themselves. That gap is where engagement breaks down.

What looks like disengagement in the data is often something else. It is the moment an alum no longer recognizes themselves in the story being told about them.

Hill’s point about Whop wasn’t that the platform had a branding problem. Knowing where something is going matters more than defending where it’s been. That’s the frame.

Alumni programs that hold tightly to the success story they were built to celebrate will keep reaching the alumni that story fits. The rest do not disappear. They just stop seeing a place for themselves in what’s being said.

More content from Week 1

• This week’s learning guide

• Keynote: John Hill, VP Story at Whop

• From Ryan: Advancement can help alumni and student creators

• From Annie: Community Is the Product

• From Kristin: AI can enhance the student and alumni experience—but not in the way you think

One of the points John Hill makes in his Keynote interview this week is that young people need to learn to “be the job” rather than just find employment. The implication is that at the heart of the modern college curriculum at this moment must be learning about entrepreneurship, and how to take what someone’s good at and monetize it.

For years, advancement teams have focused on engaging successful entrepreneurs. Colleges have established award programs and created listings of alumni-owned businesses. But there’s never been an effort to work with alumni to teach students how to make their own businesses now, with what they’re good at today. It’s clear to me that advancement teams should rethink this.

The creator economy is here, signaling a movement towards monetizing attention and teaching students how to build businesses. A few schools are recognizing this dynamic and addressing it. At the same moment that Syracuse University announced its cutting of 93 academic programs, it also announced a new position for the Executive Director of the Center of the Creator Economy, a joint initiative of the S.I. Newhouse School of Public Communications at Syracuse University and the Syracuse University - Martin J. Whitman School of Management.

To quote John Hill, “This is where the ball is bouncing.”

Inherent in this challenge is the idea that “to be the job” and earn monetize means capturing and keeping attention through digital means. The question I have is about what role advancement teams should play in helping to meet this moment. Three key components will not only help institutions thrive during this moment of disruption but also stimulate more generosity and investment.

Hire freelance alumni donors as creators.

Advancement teams, indeed, all non-profits, should hire donors as part-time team members to cover events, interview other graduates or community members, and recognize donor impact. Every institution has alumni with experience as creators, whether as a hobby or in their role as a professional roles. These talented individuals need to be added to as contributors to the stories that advancement is trying to tell.

It’s not about hiring “influencers.” Influencers have their own agenda that doesn’t always align with the school or organization.

Tell success stories from the gig economy with content, not awards

Alumni teams have focused on the achievements of entrepreneurs for many years and graduates that have led successful businesses have routinely received accolades. Young alumni typically represent a category of award with recognition going out to the most extraordinary. A few schools have recognition programs like “30 Under 30” but few recipients are those that have built a small business through a platform like Whop that provides tutorials for success in a particular video game, for example.

For schools to really help draw attention to and be a part of the creator economy, a shift is needed in the way they think about recognizing not just successful entrepreneurs, but a certain entrepreneurial spirit. It also requires widening the aperture on who is recognized and how they are recognized.

Educate on the tools that are available to build a thriving business, even if it’s a “side hustle.”

Alumni and students who have found success in the creator economy are almost certainly experts in utilizing a set of digital tools. They’ve practiced, iterated, and prototyped over and over again until they’ve been successful. There’s a strategic partnership to be had between advancement officers, career units, and entrepreneurship centers to help provide insights into the new tools and platforms available for building a business.

The trick in all of this is to create value for engagement. In other words, advancement teams focused on engaging stakeholders should be thinking about what value their alumni networks can provide that adds to what someone can find on YouTube or through ChatGPT or Claude. The real value is not just the stories of success, but in sharing the failures as well.

If the next generation is expected to “be the job,” as John Hill says, then advancement teams have an opportunity to move from storytelling to skill-building in ways that directly shape student and alumni outcomes. In doing so, they won’t just drive engagement, they’ll create value that deepens connection, builds relevance, and ultimately inspires greater generosity.

More content from Week 1

• This week’s learning guide

• Keynote: John Hill, VP Story at Whop

• From Annie: Community Is the Product

• From Kristin: AI can enhance the student and alumni experience—but not in the way you think

• From Dave: When the Story You Tell About Alumni Stops Matching the One They’re Living

During this week’s conference on Speaking Engagement, everything centers on these ideas:

The world your alumni are living in has changed.
Your engagement strategy probably hasn’t.

If you only take one idea from this week, take this:

“It’s no longer about finding a job. It’s about being the job.” — John Hill

That shift is driving everything that follows.

What This Week Is About

Across the Keynote, Breakout, and articles, we’re exploring three connected ideas:

1. Your Alumni Story Is Outdated

• Most institutions still tell a linear success story

• Many alumni are living nonlinear, entrepreneurial lives

• The gap isn’t messaging — it’s identity

What looks like disengagement is often misalignment

2. Community Is Now a Product

• People are paying for belonging

• The model that works:

  • Small groups

  • Structured interaction

  • Flexible participation

Most engagement strategies still optimize for access, not connection

3. AI Is Raising the Stakes

• More people will need to “be the job”

• Entrepreneurship is no longer optional

• Institutions must rethink their role

The question isn’t “what do we offer?”

It’s “what value do we create?”

Where Advancement Fits

This week introduces a shift most teams haven’t made yet:

From storytelling → to skill-building

• Alumni as teachers, not just donors

• Content that teaches, not just celebrates

• Networks that create opportunity, not just connection

What to Do With This

If you’re leading a team, keep it simple:

• Listen: Keynote with John Hill (Free)

• Read: Pick 1–2 articles that challenge your assumptions (Members)

• Discuss: Where are we out of sync with our audience?

Don’t Skip the Breakout (Members)

In this week’s Breakout, we push on the uncomfortable parts:

• Is “being the job” realistic for everyone?

• Are institutions investing in the wrong things?

Including this:

Universities need to “get out of the infrastructure race” - John Hill

This is where your team will have the real conversation.

The Bottom Line

Maybe it’s not an engagement problem.

Perhaps it’s a relevance problem.

And relevance is harder to fix — because it requires changing how you see your audience.

Enjoy all our content with a membership for you, your team, or institution.

Become a Member of Speaking Engagement