“I hosted a the worst webinar in the history of webinars”

I was this company’s new demand gen manager and this was one of the first big campaigns I ran. Someone on the leadership team came up with the idea to host this huge webinar about automation in back-office processes (basically a topic that should’ve been a huge hit for our audience).

We spent weeks putting it together. The product team built a live demo, we locked in a guest speaker (some influencer in our niche who charged us a small fortune), and I ran ads and email campaigns to drive registrations. Everything looked good on paper. By the time the webinar rolled around, we had over 1,000 sign-ups, and I thought we’ve nailed this.

But it all went downhill, FAST.

First, we sent out confirmation emails with the wrong link. People were logging into some unrelated event that had nothing to do with us. By the time we fixed it and sent out a new link, a bunch of people had already bailed.

Then there was the guest speaker. They were supposed to give this amazing talk about trends in automation, but their internet connection was terrible. They kept freezing mid-sentence or disappearing entirely. It was painful to watch, and the audience was dropping like flies.

And then, just when I thought it couldn’t get worse, the product demo crashed. Not even halfway through, the software just stopped working. The presenter tried to recover, but you could see the panic on their face. At that point, I wanted to crawl under my desk and disappear.

After it was over, I thought, “Well, at least we got a bunch of sign-ups, right?” Wrong. Turns out, the marketing ops team had pulled the wrong contact list for the campaign. Most of the registrants were completely outside our target audience—random Gmail accounts, students, people who were never going to buy from us.

The sales team was furious. Leadership wanted answers. I had to sit in meeting after meeting explaining how everything went so wrong. I didn’t even know what to say. It was one of those moments where you feel like maybe you’re not cut out for the job.

Looking back, it’s almost funny how bad it was. Almost. At the time, it felt like the end of the world.