The Real ROI of Events (It’s Not What You Think) (Exit Five Newsletter)

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If you want your 2025 (and 2026) campaigns to take less time and drive more pipeline, don't skip this.

🎤 Behind the Scenes of Our Annual Conference: What Running Drive Twice Taught Us About Events

Editor’s Note: Hey, it’s Dave. This week I'm doing something different. I know you love the behind the scenes stuff, so I invited Allison and Anna from the Exit Five team to talk about Drive 2025, our second annual conference in Vermont. They are the two people on our team responsible for this event, and figured it would be fun to do a deep dive with them. This newsletter is all the lessons we learned from running this thing and the massive undertaking it’s become. If you're thinking about events for your company or just want to see how we think about this stuff, keep reading. I think you’ll like this. Plus, go and listen to my full conversation with Allison and Anna here.

Events are having a moment right now.

After years of Zoom fatigue and talking to AI assistants on our phones (cut to me walking through the woods of Vermont talking to ChatGPT), people want to connect with real people again. We're all craving that in-person energy. I miss the eye contact! The nuance! The hang in-person.

At Exit Five, we went all in on events. We ran Drive for the second time this year, and we're doing it again in September 2026. Same place. Vermont. But bigger - four hundred people this time. Plus we’re doing dozens of smaller events around the country. And I think we’re starting to figure out a bit of an events playbook.

Here's what we learned so far.

🖥️ Every Event Should Start With the Landing Page (aka Begin With The End In Mind)

Most people think about the landing page last. We think about it first. And I’ve always loved this as a guardrail. Think about the headline. Picture the page. What does it look like? What do you want people to see, feel, think, and do?

The landing page forces you to answer the hard questions before you've wasted time on anything else. It’s too easy to jump RIGHT into the logistics and minutia.

So let’s get back to good marketing: What is this event? Who's it for? Why should someone come? What will they walk away with?

If you can't nail that messaging, your event isn't clear enough yet. Don't book the venue. Don't lock in speakers. Figure out the landing page first.

We learned this the hard way in year one. We had a venue and two hundred tickets sold before we even knew what the event was going to be. That made everything harder.

Year two, we started with clarity. And it showed.

🔒 Treat Your Event Like a Product, Not a Project

Here's the shift that changed everything for us: we stopped treating Drive like a one-time project and started treating it like a product.

Products get iterated. Products get feedback loops. Products improve over time.

After Drive 2024, we sent a survey to every attendee. We asked what worked and what didn't. Then we read every single response.

People wanted more time to connect. They wanted smaller group discussions. They wanted activities that weren't just sitting in a conference room.

So we built that into Drive 2025. More free time. Structured small group sessions. Hiking excursions. A golf outing. Axe throwing.

The feedback shaped the entire event. And people noticed.

🕒 Connection Happens in the "Third Spaces"

The best moments at Drive didn't happen during the sessions. They happened in between.

At breakfast. On the hike. At the bar after dinner.

We call these "third spaces." Not the stage. Not the breakout room. The informal spaces where real conversations happen.

So we designed for that. We built in long breaks. We made sure meals weren't rushed. We created excursions where people could opt in and spend hours together doing something fun.

One person told us they made three new friends on the hike who they're still talking to months later. That's the kind of outcome you can't manufacture. But you can create the conditions for it.

👥 Your People Are Your Best Content

We had panels and fireside chats. But the most valuable content came from the attendees themselves.

We ran small group discussions where 8-10 people sat together and talked through real problems. No presentation. No slides. Just marketers helping marketers figure stuff out.

People loved it. Because they weren't just listening to someone on stage. They were part of the conversation.

If you're running an event, don't underestimate the knowledge in the room. Your attendees are the content. Your job is to facilitate the exchange.

✈️ The Event Isn't Over When People Leave

Most companies think the event ends when people walk out the door. But the event ends when the follow-up ends.

We captured everything. Professional photos. Video clips. Recap content. Then we pushed it out fast. The same day or next morning.

Why? Because if you wait a week, the momentum is gone. People have moved on. You need to keep the energy alive while it's still fresh.

We also introduced people to each other during the event. On purpose. "Hey, you two should meet." That's part of the job.

And we're already planning Drive 2026. The event never really ends if you're building something that comes back every year.

✅ What Worked and What We're Changing

Here's what worked:

• The venue. Vermont is incredible. Mountains. Golf course. Spa. Pool. People loved it.
• The size. Two hundred fifty people felt right. Big enough to meet new people. Small enough to actually connect.
• The vibe. No vendor booths. No suits. Just marketers being real with each other.

Here's what we're changing:

• More people. We're going to four hundred next year. That's a big jump, but we think we can handle it.
• More structure for small groups. People wanted even more facilitated discussions. So we're building that in.
• Better communication before the event. We want people to know who else is coming and start connecting before they even show up.

📈 Why Community Is the Real ROI

Look, events are expensive. They're hard to pull off. And measuring ROI is tricky.

But here's the thing: the real value isn't in the sessions. It's in the relationships people build.

Someone told us they met their next hire at Drive. Another person said they found a mentor. A third person closed a deal with someone they met there.

That's the ROI. Connection. Relationships. Community.

If you're building a community like we are at Exit Five, events are where the magic happens. People go from usernames to real friends sitting next to you on a chairlift.

You can't put a number on that. But you can feel it.

🫵 What This Means for You

You don't need to run a conference to apply these lessons.

Start with the landing page. Force yourself to get clear on what the event is and why people should care.

Treat it like a product. Get feedback. Iterate. Make it better each time.

Design for connection. The best moments happen in between the structured parts.

Use your attendees as content. Facilitate conversations instead of just broadcasting information.

Follow up fast. The event isn't over when people leave.

And if you're thinking about events for your company, just start. We had no idea what we were doing in year one. We figured it out as we went. And now we're doing it again with four hundred people.

The only way to learn is by doing.
– Dave

P.S. Are you doing events at your company in 2026? Tell me what you've learned. Where are you investing? I'd love to get a few replies telling me about your event strategy. Did anything land with you in this email?

Btw the highlight for Drive for me: having my kids up on stage at the end. They are starting to get it. Look Kids! Your Dad is a B2B marketing legend! JUST KIDDING, they have no idea what I do - but they loved that people came to this event and that we had cookies 🙂

📺 UPCOMING EVENTS

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• November 18th: Attention and the Inbox: How Great Marketers Are Rethinking Email and SMS in the World of AI (exitfive.com/live/email-sms)

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• TODAY: Map Your IT Services Buyer Journey: Peer Roundtable and PlayBook Swap
• November 17th: Fix Your Paid Ads: AMA with Rex Gelb (Former Head of Paid Media at HubSpot)
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📚 LATEST CONTENT

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• 📰 How to Put On a Virtual Event People Actually Want to Attend
• 📰 How to Lead a High Functioning Marketing Org

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