What I learned from events this year (and what I'm taking into 2025)

You could say I’ve been buried in spreadsheets for the past couple weeks.

I know I’m not the only one, but we got a bit of a head start this year. Probably started three to four weeks earlier than last year. So, hey, that’s progress in my book.

One line item from my budget this year that’s getting some serious thought is events.

The dinner roadshow we hosted, events we sponsored, and one-off tickets to attend events at the last minute. I’m trying to figure out the role of events in our overall marketing strategy.

I’ve spent a lot of time on the road this year (and I’m wrapping it up in Philly next week with one last event this year).

So, I thought I’d share my POV on the events I attended this year. Let’s do it.

Use the destination as the hook

Location, location, location.

Some people underestimate how much a unique location can create a truly standout event experience—especially when you’re not competing with the noise of a massive city designed to host thousands of attendees.

Take Exit Five’s Drive event in September. Dave Gerhardt pulled a power move and made everyone come to him in Burlington, Vermont (a town with about 44,500 people).

Compare that to San Francisco and the Moscone Center. If I never have to go back to the Moscone Center again, I’d be totally fine.

Drive didn’t feel like Dreamforce. It couldn’t. The town’s size alone made it different.

But that’s also why it worked.

The Exit Five team leaned into the local Vermont culture. Lake Champlain, Ben & Jerry’s, maple syrup, and leaf-peeping season. The destination wasn’t just the venue. It was part of the experience.

AudiencePlus’ Goldenhour event did the same, but they went big in a big city: five-star everything in Brooklyn. Production quality through the roof (I think there was one camera person for every 20 attendees), insanely nice menus, and almost too nice for a B2B marketing event.

Like so nice, something felt off.

My takeaway: Both organizers made their events more personal by making the destination part of the experience. A unique destination can set your event apart. Use the location to build an experience people won’t forget.

Create a space for real connections

When it comes to events, it’s a numbers game.

You need enough attendees to justify costs, attract sponsors, and prove ROI. But chasing quantity can ruin the experience.

What attendees really want is to connect with their peers in person and off the record.

They want real conversations. In-house marketers aren’t there to get pitched by consultants or agencies trying to sell them something. Mixing too many different roles and personas creates competing agendas and misses the mark.

That’s why events like Klue’s Compete Week in Vancouver and Navattic’s user event in NYC stood out.

Both had a strong customer component, unlike a lot of other events. Hearing how their customers use the product, seeing execs coming up with new ideas in real time, and learning about unexpected use cases created an awesome environment.

Having customers at your event is a hidden cheat code.

They can tell your product’s story in ways you can’t. They’re living proof it works. And from a sales perspective, they can connect directly with attendees who aren’t customers yet. Their word will always carry more weight than yours.

The future of events is shifting toward smaller, curated gatherings (150 to 200 people tops) where attendees feel safe to open up, share their experiences, and learn from people who truly understand their challenges. People walking in the same shoes.

My takeaway: Invite-only or application-based attendance doesn’t just narrow the focus—it creates a space for deeper, more valuable conversations, especially when customers are part of the mix.

Balance education, community, and fun

The real magic of events is finding the right mix of education, community, and entertainment.

The presentations aren’t the main draw for me.

Sure, you can tell who loves a good slide deck by how fast their phones come out to snap pictures, but I’m there for the people. Real conversations beyond the LinkedIn B2B marketing echo chamber.

Wynter’s Spryng event nailed it.

They hosted at a brewery with food trucks, a bar that opened shockingly early (maybe a little too early), and a party where everyone could just relax. No awkward networking games, no forced personas. Just humans connecting.

But they didn’t stop there. They matched attendees with roundtables based on shared roles and interests, creating deeper conversations that felt more like a good group hang than a forced discussion.

The trick is to stop treating tracks as just “content delivery systems.”

If you’re curating a focused audience, think about tracks that reflect how people want to learn or what they hope to get out of the event.

Some want structured presentations from experts. Some love talking shop with peers around a shared challenge. Others just want to hang and reconnect in person after three years of Zoom fatigue and awkward virtual waves goodbye.

My takeaway: Survey attendees at registration to understand the “why” behind their attendance. Catching them at that top-of-mind moment helps you design an experience that meets their expectations. Not just your assumptions.

Events I’ve got my eye on for 2025

You’ll probably see us at some of the events mentioned above next year, but not always in a sponsorship capacity.

The cost to sponsor didn’t feel worth it in most cases, so we plan to be more selective about which events we’ll attend and focus on pulling off our video interview play more strategically.

Three events I’m especially excited about:

1. Pavilion’s 2025 GTM Summit next October—I had some serious FOMO from missing it this year, but it seems it’s squarely in our ICP and the exact audience we want to connect with. Go where your ICP goes. That’s the move.

2. UserEvidence’s in-person event next fall—I can’t say much yet, but I promise it’ll pull from the best of what we’ve seen this year with our spin on everything (while leaning into our roots 🤠). I pitched the co-founders on the idea, and they loved it.

3. My wedding next November—my mom subscribes to Evidently so I’d probably get an earful if I didn’t say I was very excited about this event next year. We have most of the wedding planned already (aka I got out of the way).

Stay tuned. More to come early in 2025.

Stuff I’m digging this week

• Board-level questions on the marketing budget from Dave Kellogg—I’ve been reading Dave Kellogg’s blog since 2017, and I can’t tell you how much I’ve learned from him over the years. His latest post hit me at just the right time yesterday (right in the middle of spreadsheet hell for next year’s planning).

• CyberMarketingCon 2024—We’ll be in Philly next week so come say hey. We’re getting ready for our presentation, podcast recordings, and dinner we’re co-hosting with Navattic. I’ve also never been to Philly before, so give me your best cheesesteak recs.

• 5 tips from customer marketing Leaders at Gong, Tipalti, and Trellix—Customer marketing doesn’t always get the credit it deserves. Learn from three of the best customer marketers I know so you can show real impact and use customer evidence to move the needle.

Opinions are cheap. Proof is gold.

In the latest episode of The Proof Point, recorded live at the Exit Five event, Copy.ai’s Kyle Coleman explains how AI can help SDRs succeed without compromising human connection. 

My biggest takeaways:

• AI is an SDR partner, not a replacement. Kyle explains how using AI to automate repetitive tasks gives SDRs the freedom to focus on personalized, high-impact interactions.

• AI is helping to close the SDR skill gap. By reducing busy work, SDRs can build the sales skills they need to grow into more strategic roles.

• Buyers don’t want a robotic sales process—they want to feel understood. Kyle speaks to how AI can make SDR outreach more thoughtful and relevant.

Listen on Spotify or Apple, or head over to YouTube.

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