How Pylon turned a webinar program its CEO didn’t believe in into its #2 closed-won channel

About a year ago, Cassie Carter was given the job of launching Pylon’s webinar program from scratch. Her CEO wasn’t sold on it. His question was whether anyone still attends webinars.

The first session answered that by booking five meetings right away. Today the program pulls 1,000+ signups per launch webinar with ~70% live attendance. Only conferences drive more of Pylon’s marketing closed-won revenue, and webinar-sourced deals come in at a higher ACV.

In this masterclass, Cassie walks through how she got there: the format pivot that made it work, the founder-led promotion behind most registrations, and the post-event motion that turned on-demand into Pylon’s top MQL driver.

What you’ll learn

• How to get leadership buy-in when they think webinars are dead (and which early win to go after first)
• Why Pylon moved from thought leadership to demo-led sessions, including a monthly PM-led What’s New
• The founder LinkedIn play that drives more registrations than any other channel
• How to tie webinars to closed-won and ACV so the program can defend its budget
• The post-event workflow: Salesforce sync, LinkedIn follow-up, repurposing, and paid retargeting to on-demand