Welcome to Evidently—the bi-weekly newsletter where I share my biggest hits (and get honest about my misses) as a first-time VP of Marketing. If this was forwarded to you, join the 4,000+ people who apparently enjoy watching me figure this job out in real time by subscribing here.

I’ve already written about the bet we made with Highline in past editions of Evidently (here and here). We’ve even recorded a mini-series literally called The Highline Bet, coming soon.

None of this is that.

This is the personal one. The emotions, the moments, the scenes burned into my brain. What it actually felt like to live through Highline from the inside.

Flying into Jackson on Saturday, I wanted a head start. A good night’s sleep. Space to get my bearings before the chaos began. Friends and mentors all told me the same thing: “Soak it all in. Take time to pause and notice everything coming together.”

That advice echoed in my head all week. So that’s what this is—what I noticed before, during, and after. What I felt. And why I’ll never forget any of it.

Oh, and one more thing: the part I’m now on the hook for showing—ROI.

The build

Sunday was a beast of a day. By design.

Started at 8 a.m. Didn’t stop until I face-planted into bed around 9 p.m.

Badges. Deck changes. Lanyards. T-shirts. Speaker gifts. Deck updates. Signage. Walk-throughs. More deck updates.

All the little details attendees would never notice—unless we got them wrong.

It was chaotic, but not messy. Every box checked made the pressure feel less like stress, more like focus.

And then Slack started blowing up.

We’d spun up a channel for attendees the Friday before—a last-minute idea from Evan. By Sunday, it was buzzing. Travel selfies. Side chats. People making dinner plans before they’d even landed in Jackson.

^{The energy was already through the roof.}

The welcome party

Monday night is when I first thought: we might have something special here.

The welcome party didn’t feel like a conference mixer. It felt like the kickoff to a wedding weekend. Someone said that out loud—and they were right.

Beer burros clopping through with saddlebags full of drinks. Leather koozies you could custom brand with different designs. People even snapping photos of the napkins and stirrers.

This wasn’t networking over watered-down cocktails. It was a vibe.

^{I want to come back in the next life as a beer burro.}

Most of these touches were surprises—even Evan and Ray didn’t know. Watching their faces light up alongside the attendees was one of my favorite parts of the week.

At one point, someone asked them how much they knew about the plan. Their answer: “Not much. We just let Mark and his team cook.”

Then came the first party crashers. Six people from across the street wandered in. “This event just looked so cool,” they said. “We wanted to be part of it.”

Strangers trying to sneak into a B2B marketing event? That’s about as good a sign as you’ll ever get.

By the end of the night, people were already talking about how “different” it all felt. And the best part was Highline hadn’t even officially started yet.

The activity day

Tuesday was the first big swing.

We didn’t want people trapped under fluorescent lights in a hotel ballroom. We wanted them to actually experience Jackson.

So we broke into small groups for four excursions:

• Whitewater rafting

• A scenic float down the Snake River

• A wildlife van tour

• Horseback riding into the hills

The hunch was simple: give people a once-in-a-lifetime experience together, and meaningful connections will follow.

And they did.

By dinner, the room wasn’t cold. People weren’t strangers. They’d already paddled through rapids, spotted moose, and laughed on trail rides. That did more than any icebreaker exercise ever could.

That night, we filled the Jackson History Museum for local stories and live music. Plus a custom hat bar that had a line all night. Attendees branded their initials into cowboy hats, posted photos, and tagged each other on LinkedIn.

That was the whole idea. Big strokes visible. Flourishes as surprises.

The content day

Wednesday was the main event.

I rode the gondola up at 7 a.m. (who has ever said this for a B2B marketing event?) with Madeline, our event manager from Planwell.

The car rattled quietly while my brain replayed all of the planning that went into this crazy idea. When the doors opened, everything was still. Cold air. Empty room. A panoramic view of the Tetons. Tables set. Signage in place.

Once everything was locked, I walked to the rooftop and asked someone to snap a photo.

Not for LinkedIn (though it ended up there). For me. Proof I actually paused long enough to feel it.

^{A photo for me, my mom, LinkedIn, and this newsletter.}

The thought in my head: It’s finally here. You’ve done everything you can. Now enjoy it.

Then the storm hit.

Seven sessions. Nine speakers. I was in constant motion—making sure the right people had the mic, keeping panels on track, guarding a two-and-a-half-hour buffer at the end of the day that I refused to give up.

The talks landed. The roundtables did their job. Leaders left happy. If I’m being real, product marketers and customer marketers wanted more tactical depth for their roles. With three personas in the room, that’s what we’ll need to balance better next year.

We closed with the Zealot announcement. Evan and Alex on stage. Me in the back, finally still, watching demo requests roll in before the closing keynote even ended.

That’s when the pressure finally lifted.

Every late-night thought I had about this event. Every email, DM, and Slack sent to get people to Highline. Every “I promise this is my last change” deck update. Every run of show planning meeting. Every debate about whether this crazy idea was even worth it.

Twelve months of energy, risk, and second-guessing—all crashing down into one moment in the back of that room: we pulled it off.

The payoff (so far)

And then came the public response.

LinkedIn lit up. 46 posts. Roughly 200K impressions. Nearly 6K reactions.

Attendees sharing photos from the river, the gondola, the museum. Quotes like, “The best marketing event I’ve ever attended,” and, “This wasn’t a conference, it was a feeling.”

^{This is going in my Q3 board update for next week (Les - you’ll get the rest of the Highline update on Tuesday).}

So far, the business impact in the 21 days since everyone left Jackson has also matched our gut feelings:

• NPS 83 for a year-one event (70 = world-class)

• $30K in bookings

• $415K sourced pipeline

• $483K influenced pipeline

• $820K influenced renewals and upsells

• $1.75M total pipeline impacted against a $1.82M goal

The earned media value from all the LinkedIn noise is hard to measure perfectly, but we put it at $15K+. That’s conservative too.

But when you scroll the LinkedIn feed, see the reach, and watch people posting about Highline who weren’t even there—let’s just say it blew past even my own ridiculously high expectations.

The quick learnings

What we’ll keep the same:

• No more than ~100 external attendees. Curation is the moat.

• Activity first, content second. Outdoor small-group experiences in Jackson did exactly what we’d hoped—created trust and shared memories before content day.

• Surprise and delight. The koozies, the hat bar, the touches people didn’t see coming but 100% noticed.

• Invite-only. The filter mattered.

• Slack channel. Spun up the Friday before, it became the heartbeat. By the weekend, it was blowing up.

What we’ll tweak:

• Securing more commitment. Invite-only with no ticket created soft commits. 75 people bailed leading up to the event and there were a handful of day-of no-shows. Next year: add skin in the game via a deposit, ticket, stricter RSVP parameters, etc.

• More tactical content and roundtable time. Practitioners wanted more time and tactical depth. Next year: more rooms where people can do the work—playbooks, talk tracks, customer sessions that aren’t sales pitches.

The end (for now)

People spent their own money to get to Highline. We spent more than we’d ever spent on a single marketing line item. And I carried the weight of all of it because I believed in it.

And then it worked.

The pride I’m still feeling two weeks later isn’t just from the pipeline or the posts. It’s from watching the event get experienced, word for word, exactly as we wrote it in our planning brief months earlier. Our playbook, spoken back to us by the market in their own voices.

A snippet from the OG Highline event brief I created on November 22, 2024.

That’s never happened to me. But it did.

Highline went from pressure to pride in three days. It’s the number one accomplishment of my career so far.

And it bears repeating: I’ll never forget it.

Stuff I’m digging this week

• Highline 2025 recap video—The first piece of content from Jackson is live, and I keep rewatching it. More coming soon—docu-series, keynotes, and some tiny mic interviews that tease our upcoming Evidence Gap 2025 report.

• Mojo PMM from Eric Holland—Mojo PMM takes your product messaging and turns it into custom GPTs that make it easy to write webpages, ad copy, and talk tracks. The idea, the creative, the execution—it all hits. I got to hang with Eric at Highline (fake mustaches included), and I’m pumped to see him bring this to life. 

• We’re hiring a Product Marketing Manager—Coming off Highline, a funding round, and the Zealot acquisition, we’re adding a PMM to help cover more ground. It’s a career-defining role and our team culture speaks for itself. What people saw at Highline was just a glimpse.

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