From 0 to 20,000 attendees: Event marketing insights from Jay Schwedelson

Part of Beyond the Venue: Event Marketing Bootcamp

Event marketing isn’t without its challenges. From dealing with low turnout to making your event stand out in a sea of competitors, the process can test even the most seasoned marketer. But it doesn’t have to be a guessing game.

Jay Schwedelson—a marketing visionary behind some of the most successful virtual events—is sharing his proven strategies to make your events work for your business. Having grown his own virtual conference to a staggering 24,000 attendees, Jay knows what it takes to drive engagement, deliver value, and, yes, keep things interesting.

Let’s break down his top insights from our recent Event Marketing Bootcamp, in his conversation with Jordan Arnold (Head of Global Sales & Strategy at RingCentral), into actionable steps for your next event.

Rethinking webinars

Jay makes one thing clear: the word “webinar” could be holding you back. “The actual word is a boat anchor,” he says. Instead of relying on a tired format, shift the focus to what truly resonates with your audience.

His advice?

• Highlight the topic first, not the format.
• Use engaging terms like “live event” or “virtual workshop.”
• Emphasize the value attendees will gain, and make that value obvious upfront.

Building experiences that stand out

How do you get people excited? Simple: offer something different. Infuse your event with personality and tangible takeaways. Jay puts it this way: “If your event feels like you’re just reading off a PowerPoint about industry updates or best practices, no one is coming to your next one.”

The importance of brutal honesty

Jay’s team uses what he calls the “Does It Suck?” committee: a no-holds-barred process for evaluating ideas. As harsh as it may sound, this approach ensures that every concept or session aligns with audience expectations and drives engagement. Consider building your own internal feedback mechanism to ensure quality without compromise.

Redefining monetization

Charging admission isn’t the only path to ROI for virtual events. In Jay’s model, he keeps events free for attendees to broaden reach, while giving sponsors meaningful ways to engage with a highly targeted audience.

One tactic? Sponsors can ask custom registration questions to generate qualified leads—a win-win for both event organizers and sponsors looking for high-value prospects.

Optimizing for speaker impact

The days of promoting events with static thumbnails and bland bios are long gone. Jay’s approach prioritizes action from speakers.

Here are a few of his top strategies:

• Ask speakers to produce 30-second tips or teaser videos in advance.
• Require them to promote the event on their own social channels.
• Make promotional efforts part of the speaker agreement.

Speakers, no matter their level of prominence, need to contribute to the event’s visibility. Setting clear expectations ensures everyone has skin in the game.

Solving the on-demand dilemma

It’s tempting to make event recordings available forever, but according to Jay, that might diminish live attendance. Instead, he recommends an “earned on-demand” model: require attendees to participate in the live event for a set amount of time (e.g., 60 minutes) to unlock access to recordings. This approach builds FOMO while encouraging deeper live engagement.

Final advice: Push boundaries

Jay’s overarching reminder to event marketers? Stop following the same well-trodden paths. Play the game differently by rethinking traditional formats, embracing creativity, and actively experimenting with new ideas.

Your next virtual event doesn’t have to look like everyone else’s. With Jay’s advice in mind, you’re positioned to create experiences that are engaging, effective, and, most importantly, memorable.

Looking for more insights? Jay’s upcoming 100% free virtual event, Eventastic, hosted by Guru Media Hub, is the world’s largest event about events, offers even more actionable strategies to elevate your approach. Don’t miss it, happening on June 5-6, 2025.

Missed our Event Marketing Bootcamp? Sign up and watch the replay of the entire conversation with Jay.

Watch the replay

Originally published Jan 13, 2025