Why We’re Retiring Drive and Hitting the Road in 2027

After three years of hosting Drive, our annual event in Vermont, we’ve made the decision to pivot our strategy heading into 2027 and retire Drive.

I know. I know…

Drive was awesome.

Drive was summer camp for B2B marketers.

Drive was LinkedIn, but the good version: in person. Everyone was super kind, approachable and – normal. At a time when we need real human connection more than ever, we made new friends and bonded over career moves, families, and life outside of work.

Over the past three years, 800 people flew to Vermont from places as far as Hawaii, India, and Israel for a conference about B2B marketing. 

That’s not normal. We clearly have something special. So why walk away from it? What, are you crazy? Haven’t you read the business books? Double down. Keep the main thing the main thing!

Well: speaking of business books, Dan and I are always passing these types of books back and forth, and one that has stood out over the years is Ben Horowitz’s The Hard Thing About Hard Things. It’s all about the realities of building a startup when there are no easy answers. This is one of those hard things. Killing something that is working. Something that’s made a real impact on people’s lives, careers, and selfishly has become our team’s favorite week of the year.

But after Drive this year, we realized we were at a bit of a crossroads. Are we building the next giant tradeshow for marketers? Is Drive the next UNBOUND, Dreamforce, or SaaStr? Or should Drive be a festival in the desert? Burning Man for B2B marketers looking to find themselves.

Drive is stuck somewhere between a community meetup and a tradeshow, and we need to be intentional about what game we want to play.

Putting on an event like Drive is (candidly) a lot of freaking work. This becomes a year-round, full-time job for a bunch of the team. Ask Dan and Allison and Anna. It’s basically like planning a wedding for 400 people every year. Navigating speakers, sponsors, travel, contracts, venues, dietary restrictions, A/V, the crazy Frenchman who wants to bring a local jazz band to his keynote last minute (we love you Louis; don’t worry, you’re not the reason for this). The point is, the event business is not for the faint of heart, and we carry that stress 300 days out of the year.

So for 2027, we’re taking a break from the big “annual conference” feeling – and instead we’re going to hit the road. For three years, we asked you to come to Vermont. Next year, we’re coming to you. We’re rebuilding our event strategy around hub cities: Boston, New York, San Francisco, Toronto, and Austin*.

*For now. I can already hear you in the comments about Chicago and the UK and everywhere else we should go. We’ll get there. The good news is you don’t have to live in one of these cities. If you’re up for a trip, you’re welcome at any of them.

We’re beginning to plan these events now, but here’s what this might look like:

• A happy hour at a fun spot in Boston with 100 marketers from the community.
• A morning breakfast in NYC for CMOs on AI transformation, then an evening meetup with good food, content, and a big crowd. We did a version of this earlier this month hosting a live podcast with Varonis CMO Rob Sobers, and it was a huge hit.
• A half-day working session in Austin for B2B marketing leaders. It’s off the record, so no video, no notetakers, just what’s really going on inside their companies and where they need help.
• And there’s our Marketing Leadership Retreat, March 1–3 in Scottsdale, with 150 in-house marketing execs. It has peer-led breakouts in small groups matched by role, company size, and go-to-market motion. The keynotes are Alice de Courcy (CMO, ZoomInfo), Ethan Braden (CMO, Texas A&M), and Dave Kellogg (EIR, Balderton Capital), and there’s plenty of hiking, golf, and poolside conversation outside of the conference room.

And we get to go build all of it with what we learned from Drive over the last three years.

We’re already cooking up ideas for what’s next, but we wanted you to hear about our plans for Drive first.

To everyone who came to Vermont: thank you. Drive helped launch us as a proper company and a global community. Most of all, it got us in a room together, IRL. That’s where the good stuff happens.

So for 2027 it’s more cities, more often, closer to home. Same Exit Five energy.

(And now that I’ve written this all out, there’s no way this is less work. But we will figure it out.)

Thanks for the memories, Drive. See you on the road next year.

– Dave, Dan, and the Exit Five Team