In this BOOM! interview, host Ben Hindman talks with Jason M. Lemkin, CEO of SaaStr, about the evolving landscape of events post‑pandemic. Lemkin argues that large‑scale conferences will not be replaced by digital formats but will adopt a "perpendicular" model— a dedicated, high‑capacity digital experience separate from live streaming, enabling hundreds of thousands of virtual attendees. He highlights how event software is merging with collaboration tools (Zoom, Teams, Google Meet) and predicts significant M&A activity in that space. On sponsorship, Lemkin explains that field marketers must shift from raw lead lists to intent‑based leads, delivering both depth and breadth of qualified prospects. He outlines two ROI‑focused event strategies: deep investment in a few marquee events versus a ubiquitous, smaller‑scale presence across many events, both amplified by digital capabilities. Overall, Lemkin sees a bright, still‑early future for digital gatherings that can surpass in‑person events in scale and richness, provided the right technology and strategic approach are employed.
Chapters
If you're a field marketer speccing out your sponsorship spend, well, hold on to your scanners and pop your banners, 'cause this conversation with Jason M. Lemkin got a little sassy.
To the cloud!
Welcome to BOOM!, a show about the innovation explosion in events and the tech stack. I'm Ben, I'm the co-founder and CEO of Splitit. Splash is an event marketing software for your live, virtual, and hybrid events. Today I'm talking to Jason M. Lemkin. He's the CEO of Saastr. He's an investor, an entrepreneur, and an event planner. That's a rare combination. The guy has a unique and sharp perspective on everything tech and everything events. Saastr Annual has been the conference at the center of the cloud revolution. Saastr was started in 2012 as a blog. They hosted their first conference in 2015, and now they claim the world's largest community of SaaS executives, founders, and entrepreneurs. SaaStr was one of the first conferences to cancel due to the pandemic, but has bounced back with a fully online conference this December, which is set to welcome 50,000 attendees. I had a conversation with Jason M. Lemkin and I pulled some of the highlights of the conversation here. I think you're gonna love it. We talk about things from a perpendicular event, all the way to what is next in the collaboration suite. Let's get into the conversation. Jason, great to see you. Thanks for joining us on BOOM! Okay, first question. As you look towards the future, how do you expect digital events will continue to evolve?
I don't think SaaStr or Dreamforce or any of these things are gonna be replaced on its own by digital, okay? And we can talk about why. But what has happened as the tools have been brought forward a decade, is you can have user conferences, you can have customer conferences, you can have prospect conferences on the internet that you wouldn't— you couldn't have in the real world. It's too expensive, it's too complicated. I think the big events will have a much better digital component than they ever did. It will be on steroids, okay? And that will be all fired through software, right? A few folks like Web Summit will build their own, and everyone else will buy, okay? Much more functionality, not live streaming, an order of magnitude more functionality for the big events. And then digital-only events will not replace IRL events like they have since COVID They will be better. They will be richer. They will connect more people. They will have more content, more interactions. The truly great digital events were worth it, right? And so everyone's gonna try to do that, right? And you're gonna need tools and software because the crappy stuff we had before March, none of it did it, right? None of it did it.
Okay, next question. As you look post-pandemic, what's your expectation for how event formats or event planners will need to evolve?
They will have perpendicular events going forward. So they will not have a hybrid event, which is live streaming. Like, that didn't work. No one tuned in. The engagement sucked, right? Instead, you will have a perpendicular product where it's not live streaming, it's the rest of your community. It's the other— of the 15,000 people that can attend SaaStr, we want to have 100, truly 100,000 attend digitally next year.
Wow.
And it won't be the same. They're not going to get to bump into people in the hallways, are they? They're not going to have the same experience with, with the roundtables and the meetups and the jobs board and the parties and the, the Meet Zendesk in Person. And they're not going to have that. And that's okay. But they'll have a different experience that will also be rich. That's why it's not hybrid to me. It's this perpendicular experience where we— it's more work now. Next year there'll be more work because you will have to have this horizontal perpendicular content for the rest of your community, and the only way you'll be able to keep up is with tools, with software.
So I'm curious, as this is a show for event marketers, have you seen any new trends or evolutions in the event tech stack that are worth noting?
Workplace collaboration, internal is big, but external is really big too, right? External collaboration is a huge part of it, and the fact that that would meld with event software was something no one, you know, predicted before. COVID Open up, open up your, your, your, your Gmail, especially even on your phone if you're on an Android device like me. You know what's there? Google Meet, right? Zoom is getting into events, right? And why is Zoom getting into events? Because it wants to do session registration, and it— no, it's because digital events crossed over into collaboration software, right? That's why Microsoft Teams has limited events capability now, right? It's because we never thought of event software as collaboration software before COVID right? That's what's powerful. And that's, there will be M&A there, there'll be big M&A there, there'll be activity there. I don't know whether that really drove BlueJeans or whether that was an opportunistic attempt to compete with Zoom without doing the work, but we would have never thought of event software as collaborate, maybe you did, but very few of us would have thought of it as collaboration software before, right?
Okay, next question. Jason M. Lemkin, as you have looked at the sponsorship game evolve in a digital-first world, what have you learned? Any strategies you can share with us?
I did not know this until March of this year. I've been doing SaaStrangel for 2015. I did not know until March of this year why sponsors sponsor. In cloud, 40% of leads come from field. 40%. Everyone gripes, every field marketer gripes about every event from Dreamforce on down. They gripe about everything. But they need to deploy the capital because it works. It works. Does it work perfectly? Does it work as elegantly as a Google AdWords? No. but people go, buyers go to events, buyer goes to events to learn, and buyers go to events to talk to someone they've only talked to over Zoom. And buyers go to events to make decisions. At first we saw at SaaStr, our first two events, we had no revenue. We had no sponsors, our first two events, because budgets were frozen, right? And then by our third one, they're like, digital events suck, but we'll try it. Then by the fourth one, we're like, we can get you thousands of leads. And they're like, well, blah, blah, blah, blah, blah, digital. Like, well, where else am I going to get it? So you got to try. And then they see that it performs, right? So you need to deliver depth and breadth in digital. You need to deliver the prospects and you need to deliver more of them. And you need to understand why, because even if you deliver high quality prospects, it's still not the same as talking to Ben in the booth. Okay. It's not, it might be better. Because I get to talk with the CEO over a Zoom instead of talking to an SDR in a booth. It might be better, but it is different. So you need depth and breadth. Now, one thing we don't do that everyone does that's smaller is they give you all the leads. Like, we have 800 people sign up, we'll give you all the emails. Is that worth anything? No, you want intent. So we only give folks the leads, like a booth, that say, hey, I want to come to talk with this sponsor. But they all have intent, and this lack of intent is destroying the notion of a lead for digital events. No one— people think they want the list, but they don't want the list. They want a list that wants their product.
Okay, so what are the top field marketers doing to drive ROI and to get results?
There's two strategies for events, right? And you can do both, but only if you do both. You can do— you can go deep and do a couple events in your industry, right? And you see it at Dreamforce, at least you used to. People would invest mass amounts of money. You would see it at RSA, you would see it at You even see it to some extent at Web Summit, and you see it at ShopTalk for e-commerce. People go all in on one or two events, right? And then you could blow a million bucks or more including soft costs, right? Easily, right? Or you do the everywhere strategy. I'm gonna be at everything because yeah, maybe I'll only have the smallest booth at ShopTalk, but I'll be at every e-commerce event in the industry. So my, all of my prospects will see me, right? And marketers have different strategies. You've gotta do what you're good at. And so I think for digital, it's the same, but on steroids. Right? You either gotta pick a couple things and lean in deeply, but lean in even more. Get your brand all over, get in front of everybody, or be everywhere and really nickel and dime it because you may see lower ROI. Like anything in events, if you don't put in the effort in, you don't get the effort out. If it doesn't provide value to CEOs or founders, we won't take their money. It doesn't work. Maybe it works for other people, it doesn't work for us. We can give you the data, it doesn't work. We don't allow it. But one has slipped in and it was the worst performing thing we've done at all levels.
Okay, so I think I'm hearing you say that net-net you see a bright future for digital and virtual events.
It's still early days. It's still early days, right? But I think I don't even like that even though we're stuck, it's like I don't like the term SaaS or cloud. Digital events don't make sense either, but we're stuck with the term. But I don't know, I'm not convinced they're events yet. I believe they're gatherings. A gathering could be bigger on the internet. This is so what we learned from social media. A gathering can be bigger, right? So your, your, your digital event should be bigger and better than your IRL event.
Big thanks to Jason M. Lemkin. We got a ton of downloads, everything from new thoughts on the collaboration suite to perpendicular events, a term I have never heard, but I'm planning on tweeting and using 7 times tomorrow. If you like what you heard today, make sure to share this with an event professional you love. Like, subscribe, and come check us out next time as we explore the innovation explosion in events and the tech stack. See you then.
