I’ve never carried this much weight, visibility, and expectation on a single project

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 and you like what you saw, you can subscribe here.

Last year we spent over $100K on event sponsorships. We vetted the lists. Got the sponsorship decks. Asked for proof our ICP would be in the room.

The reality didn’t match the pitch I heard.

Agencies and fractional people on the hunt for their next client. Marketers from B2B companies that don’t look anything like the ones we’re trying to reach.

We went into events like Spryng, Drive, and Cyber Marketing Con knowing they were smaller, more curated, and not built around sponsor booths. We were fine with that. But we still expected to have real conversations with the right people. That part fell short.

So we treated those events as content plays, too—something I’ve written about in Evidently before. We booked time with marketing leaders we respect (including a few target accounts), and turned those interviews into months’ worth of LinkedIn content.

The content play was a hedge. If the sponsorship didn’t deliver pipeline, at least we’d leave with something useful. And it helped.

But the whole time, I kept thinking:

What if we stopped trying to make someone else’s event work for us and built the one we actually need?

Where it started

The idea came up casually last fall in a conversation I had with our co-founder Ray.

I told him I’d been thinking about taking everything we learned from last year’s events, skipping the sponsorships this time, and doing our own. Same lessons, our format, done right.

Ray didn’t push back. He agreed and said I should talk to our other co-founder and CEO Evan about it.

That’s when it got real.

This kind of thing comes with cost, risk, and very public accountability. I’ve never hosted an event at this scale. If it doesn’t go well, there’s nowhere to hide. And it’s on me.

So I built a full event brief with clear goals, attendee mix, budget needs, and what success would actually look like. I needed to get Evan, Ray, and myself on the same page before we spent a dollar.

Evan didn’t just approve it. He got excited. More excited than I expected.

That gave me the push I needed to move forward. No waiting. No half-launching. Just go big and send it time.

What we’re building

Highline is an invite-only gathering for 100 in-house B2B marketing leaders. August 19–20 in Jackson Hole, Wyoming.

We’re bringing together Director-level+ across product marketing, customer marketing, and marketing leadership—the people we market to every day, and the ones working through the same challenges we are.

Day 1 is all about getting outside and actually spending time together.

No lanyards. No stage-mic networking. Just trail runs, fly fishing, long dinners. Whatever gets people to drop the LinkedIn persona and talk like humans.

Day 2 is where the content kicks in.

Tight keynotes. Curated roundtables. Fast lightning talks. No filler, no recycled slides, and no pretending panels are anything but panels.

Jackson isn’t just a location—it’s the point. You slow down, you talk, and by the time content day rolls around, you actually know the people in the “room.”

Most B2B events are filled with the same companies, saying the same things, to the same people.

We’re not building another hallway full of marketers marketing to marketers. We’re curating a mix of fresh perspectives, different motions, and voices that aren’t already on every stage.

That’s the kind of “room” we’re trying to build.

Who’s in the “room”

Jackson isn’t exactly cheap. Getting there, staying there, hosting an event—it all adds up.

That’s why we’re covering the full cost of the event itself. Every meal, every activity, every session. Once you’re in Jackson, it’s on UserEvidence.

Attendees cover their flight and hotel through our room block. We did that on purpose—to make it easy to say yes, especially for the right people.

But when we’re putting that level of investment behind it, we’re going to be selective. Every “yes” matters.

That includes:

• Strategic customers

• Contacts from open opportunities

• Dream, best-fit accounts that align with where we want to grow

This isn’t a UserEvidence customer event either. We’re using our #1 marketing bet of the year to strengthen relationships, accelerate deals, and create new opportunities.

The response so far

Less than two weeks after the full announcement, we’ve already confirmed 32 through direct outreach and we’ve got 77 more applicants we’re reviewing. We’re aiming for 100.

Most of that came from early LinkedIn promotion, email outreach, and a handful of personal invites. Now we’re doubling down on one-to-one follow-up from Sales, CS, and our Leadership team to keep building the right “room.”

Names like Kyle Lacy, Kacie Jenkins, Devin Reed, Jen Allen-Knuth, and Julien Sauvage are already in. One comment even called it the Met Gala for B2B marketers:

What I’ve learned already

1. The pressure to deliver is very real
   
   During a final interview back in February, a candidate asked Evan what he was most excited about across the entire company. Without hesitation, he said this event. I felt it. This isn’t just another marketing play. It’s the one we can’t afford to get wrong. And the pressure that comes with that doesn’t live in a spreadsheet. It follows you around until you make it worth it.
   

2. I’ve never done this before but I know what good looks like
   
   This is my first time running something at this scale. But I’ve been to enough events to know what works and what doesn’t. What creates momentum and what creates noise. The playbook didn’t exist, so we built the one we wish we had.
   

3. This big marketing bet has to put big pipeline numbers on the board
   
   We’re not throwing UserEvidence slides at people or running breakout demos. But the intent is clear. This event is designed to strengthen customer relationships, accelerate in-flight deals, and create new ones with the right accounts.

4. Trust gets built before the content starts
   
   That’s why Day 1 is outside. People don’t connect over slide decks. They connect on the trail, at dinner, in the quiet moments before the structured stuff begins. That’s where trust starts. And when Day 2 rolls around, the content hits harder and the follow-up happens naturally.

5. There’s no shortcut to building something like this
   
   We’ve got help (event agency Planwell and a great Jackson-based partner) but we’re running this lean. And building something from scratch still takes everything. Every detail. Every decision. Every name on the list. This event has quietly become my number one job. And I’m not sure I’ve ever carried this much weight, visibility, and expectation on a single project. It’s exhausting. But I know it’s going to be worth it.

The stakes are high but that’s the point

We’re still building. There’s pressure. There’s risk. And yeah, I’m nervous. But I’ve never felt more sure that this is worth doing.

If you’re an in-house B2B marketer and this sounds like your kind of “room,” we’d love to see you in Jackson.

Apply to attend Highline here. Every application gets a real look.

Playing The Long Game

When you take a new role, especially your first marketing leadership job, you’re betting on a person. The CEO can make or break the journey.

For season 2 of The Long Game, I “sat down” with the CEO of UserEvidence (aka my boss) for a mix of real conversation and fresh powder. TL;DR: he was worth betting on.

What we got into in episode 1:

• Startup life in a mountain town. What it’s actually like living and building a company in Jackson Hole.

• Early career arc and side quests. Stanford, SurveyMonkey, the leap to CEO, DJing Coachella, volleyball championships, and throwing parties in the Tetons.

• Life beyond Zoom. How being a dad, snowboarder, and mountain-town local has shaped his perspective and pace.

Watch it on YouTube. Episode 2 drops later this week.

Hold up—what does UserEvidence do again?

Product marketers, marketing leaders, and customer marketers need more than generic testimonials to prove value.

UserEvidence helps create real customer evidence that Sales, Marketing, and Customer Success teams can use to increase buyer confidence.

We make it easy to collect and share case studies, testimonials, competitive intelligence, product stats, and ROI data—proof that helps move deals forward.

Need a stat to prove ROI? A competitive insight to handle objections? A case study that closes the gap between interest and decision?

UserEvidence helps you capture and share the proof buyers need.