SaaStr Insider Webinar: AI Day Recap and Insights

In this SaaStr Insider webinar, host Jason Lemkin (Speaker A) and panelist Waylon McGill recap the recent SaaStr AI Day digital event, highlighting standout sessions such as Runway's founder Siki, Contextual's deep technical talk, PagerDuty's AI agent discussion, and IBM's trust and security focus. They discuss practical takeaways on prompt engineering, improving LLM response quality, and the varied maturity of AI adoption across SaaS companies—from early automation to enterprise‑level integrations. The hosts share sponsor performance metrics, noting view spikes from 3,000 to 17,000 and hundreds of qualified leads generated. They explain their live‑streaming workflow using Restream to broadcast on X/Twitter, YouTube, and other platforms, emphasizing the importance of treating digital audiences like physical seats. The conversation shifts to the value of digital versus in‑person events, the logistics of sponsor booths, and the upcoming SaaStr Europa and SaaStr Annual (including AI tracks and an AI summit). Resources such as slide decks on SlideShare, recordings on YouTube, and contact information for follow‑up are provided. The tone is informal, enthusiastic, and promotional, aimed at informing the SaaS community and encouraging participation in future events.
Chapters
Looks like our stream is going live. Welcome, welcome. Okay, starting stream, starting. Great. Welcome to another Soundster Insider webinar. We do these every Thursday. Let me get Waylon as a panelist here. I think our Restream is just a little tired after all the streaming we did yesterday. So. Took a minute for us to get going, but I see people watching the livestream. That's awesome. Let me just make Waylon a co-host. Hello. Okay.
There we go.
There we go. I know I was like, even my, I had to like change my Restream key. I was like, we did so much streaming yesterday that my poor Restream and Zoom were so tired. It's like it wanted to sleep in today.
That's all right. We're here now.
We're here now. Yeah. Gonna get it going. So yeah, we thought— let me just share my— one of my screens here. We thought we'd take the time today just to recap about AI Day and then chat about what's coming next. I know it's the end of the quarter for many of you as it is for us. It's been a busy week. So you may not have had the chance to watch AI Day. But yeah, we wanted to just share a bit about, you know, our thoughts on AI Day and also share a bit about some of the sponsor results as well. As well, just because they were really good actually. So I thought we would share a bit of that with you guys today and then chat about what's next for SaaS and then how we're building off of AI Day and what we're doing next. So yeah, Waylon, it was your first SaaS digital event, I believe. What were your kind of initial thoughts on it?
Well, I think it's great. I mean, it's obviously comfortable being at home, taking in great content from the comfort of home. So that was really nice. I thought the content was really great. Obviously with shorter sessions, people are really forced to trim the fat and there's some really interesting takeaways and some things that, you know, made me want to apply. I don't know if we're getting into specific sessions, but I thought Stiggy's session about being everybody's like prompt engineer, it kind of made you think that there's so much that can be automated and the amount of work it takes to automate it is maybe not as great as people think. And then some of the really interesting stuff just around how to get better, more reliable responses out of these, you know, large language models like ChatGPT, just like saying things like, you know, think hard about this, or, you know, my job depends on me getting this right. And that actually makes the models be more careful and give you higher quality answers was really kind of mind-blowing.
Yeah, no, it's really crazy. I'm like, the amount of content we had was, you know, a lot. It was a lot to consume. I know it was like a full half day of content back to back. I did see a number of folks going from session to session like it was, you know, an in-person event, which is fantastic. I will say, yeah, we can talk about a few specific sessions that I think were definitely standouts. The runway one with Siki, who is their founder and CEO. Yeah, it was fantastic. Great closer to the day. Yeah, I'm definitely going to try and steal his prompts that he uses in Zapier. I was like, oh, we could use those at Zaster. They're pretty good. That was a great one. I know, from Contextual who spoke at SAS Re:Annual and then did his solo session yesterday. Great session yesterday, super technical. And I think it was interesting to see how engaged the audience was on that one. We were a little nervous of being like, OK, this might be a fairly technical one. But folks were super engaged, asking really technical questions back. So that was great. Some of it I didn't even fully understand. Extremely technical, but no, that was great to see that, you know, we kind of had different— I think right now there's just such different levels within the SaaS community of like how far along people are in their adoption and implementation, right? Like obviously folks like Siki who think about, well, you know, he's built a product that is AI-based, but he just, you know, has fully embraced AI in his day-to-day, like is so far ahead of, you know, me and us and and how he's, you know, how he's using, you know, Zapier and ChatGPT to automate like his sales process. But I was like, that's such a great starting point for so many people to be like, okay, let me use this to improve my sales process to make it a little bit better. And then, yeah, you've got folks that are, you know, you know, chatting more about integration. So, you know, the— I think it was the— yeah, the VP of Product from Prismatic who was talking all about like how they use, you know, AI in their integrations. To kind of like layer on and enhance what they're doing. So yeah, I think there's different levels right now of adoption and implementation, but folks are, you know, and some folks have been doing this a really long time, like just 'cause it's kind of been taking off now. So it's top of mind, obviously it's top of mind for us too. But they're, you know, to that point, a lot of our speakers have been doing this for a really long time. I know Calvin from Dialpad, right? Dialpad's been doing AI for a really long time too. They've built all their own models. That's what they kind of showed yesterday. Lots of folks been doing this with, you know, varying degrees, but usually like great degrees of success and how they're thinking about AI and going forward. And so yeah, hopefully it was helpful to the SaaS community to see some more of that, you know, and then, you know, seeing things from folks like Shopify who are doing it, you know, at more of an enterprise level. Cisco's, I thought was like a really good, it was, it was both like a high-level explainer and then also kind of a deep dive in how they technically are using, you know, AI there. You know, IBM was talking about, you know, how to make it trustworthy. I know there's a lot of, I think a number one question, and it was a thread and, and theme in a lot of the sessions yesterday was like, you know, obviously security, like data security was like a big top of mind thing for a lot of folks. They're like, you know, the moment you kind of ask customers to give you all this to run it through AI, they, you know, become nervous, which I, rightfully so, right? You become nervous of like, okay, what's happening with all that data? What is it gonna do with it? And so I think, yeah, good session with IBM there on just how to kind of combat that and kind of like ease the nervousness there. Any other ones that were standouts for you, Waylon, just in particular sessions?
Well, I thought from the PagerDuty session with Jason, that was really interesting as well. Just understanding like—
Yeah, great kickoff.
Where you think you can totally automate, you know, AI agents versus AI as like a copilot. And, and that was a really interesting conversation. I think one of the interesting things from the IBM session as well, like a couple interesting things there. One was how much of like HR questions and stuff they've been able to automate. I think they said something like 90 to 95%. Yeah.
That is surprising, right? Because you're like, okay, usually HR has to be done IRL. Yeah.
And to be able to get like answers super quickly, that's what people want in a company when they want to understand policies around something and to be able to query and get answers super fast was obviously a really interesting use case and somewhere where it seems like you can kind of eliminate that human in the loop. But also just understanding that the way they do AI, like all the, everything that their models are trained on is all publicly available. So, you know, just like kind of upping, like you said, the trust and responsibility elements of AI, because I think that's a big part of what's slowing some people down. And as you saw, if you can go fast with it, there's like almost unlimited upside. It was really cool to see how far along some companies are and kind of paint like a North Star of where you should try to get to.
Yeah, no, yeah, so many good learnings. I think too, I, the Patriot Duty one was such a strong kickoff and I know we're trying to write it up and put it on to Aster if you guys missed it. The live stream for any of these sessions you can watch now on our YouTube channel. So they are all there and recorded. Lots again, it's a lot of great content. You know, I don't think there was a session that was a miss yesterday. So lots of learnings there. Very tactical to dive in on. But yeah, I do like that. That one too was like, It obviously was a lot about AI. That was the theme of the day, but still, you know, kind of overarching and like just talking about just, you know, the implementations into SaaS and kind of like the, the cross between the two. It was nice to see with PagerDuty and how they're thinking about all that. So yeah, no, that was a really great session to start the day. I know there's a lot of questions too we didn't get to, so we'll try to get to them next time on like a Workshop Wednesday or something. But yeah, lots of, lots of engagement yesterday too, I would say. You know, usually we do Workshop Wednesdays on Wednesdays. We did AI Day. So yeah, great to see that. The other thing I'll call out, and let me see if I can get my screen share to just flip here, is one thing that is a continuous learning, I think, on our digital events versus, you know, in-person, and something we see also at our in-person events is, let me just show you guys a little bit of the livestream, because I think this is something that people don't, I know people are like, oh yeah, we livestream our event, whatever. Like it's, it's kind of an afterthought. And there are other, you know, events and maybe more consumer events that take livestream extremely seriously. Like, you know, Coachella's next month. They, they take livestream extremely seriously. If you think about, you know, the number of folks who are going to Coachella but in person, but are also going, you know, to the livestream. Yeah, you, you can like 10x, 100x your audience on the livestream, which is crazy to think about because let me just flip my screen here. But crazy to think about in the sense that like so many more people are, you know, watching this and there's already such a windfall of folks there in person. And so I'll show you guys my or our Saastr's Twitter account just to show you some of what we've seen on livestreaming. We probably haven't talked about this in a while on this format at least, because we haven't done a digital event in a while. But let me share my screen here. So case in point, I don't know if this is going to make some kind of matrix window because we're live streaming this webinar. I'm like, literally, you can see us live streaming this webinar. You know, there's only a handful of people in the Zoom room, but there's 100 more people on Twitter watching this, right? So if you think about 126 people now in the room, you know, you're like, that's a pretty good crowd. That's a pretty good audience. Like, You know, okay, 130, like 4 people just joined now, right? Like that's a pretty good audience. I'm gonna scroll off that one so I don't make some kind of matrix glitch. But that's a pretty good audience, right? And something we try and explain to folks. And then yeah, you'll see, you know, we have, we've tweeted some yesterday. So let me scroll down to some of our AI Day tweets. But yeah, we live streamed everything. So you can see, you know, things like this one where Siki's has 17,000 views. I'm like, wow, as many people who come to— 17,000 people is a ton. That's like, well, I'm hoping we'll get to 17,000 IRL this year in person. But yeah, I'm like, but that's over 3 days. I'm like, this is literally all at once for 18 minutes. So kind of wild when you look at it that way, right? Like, lots of engagement on these live streams. It is something we do for our digital events. It's something we do for our in-person events. It's really great exposure. So, you know, if, if, if you are wanting to have your CEO also have 17,000-ish views, definitely chat with Waylon, you know, he had a fair amount of sponsors and partners take part in yesterday's AI Day. I'll try and scroll down a little bit here and just show another one. So yeah, here's another one. I'll resume my share. I'm trying not to, Scroll too much on the Zoom. Here's another one from Customer.io. You know, this one has 15,000 views from yesterday about, you know, like using AI to kind of expedite customer acquisition since PLG is, you know, too slow if you can't get everyone on the same page. So another good one there. Lots of really great views, really great interactions. And I think notice, you probably won't see it here anymore, but noticeably too, a lot of these were in real time. So it was something we were monitoring in our internal Slack of, you know, these were literally getting thousands of views during the, during the actual sessions themselves. Obviously a lot of folks have been watching the replays. It is something too where I do feel like specifically on X, you know, we, we livestream, we use Restream as you guys have probably heard, but you can use Restream to, you know, livestream to X, LinkedIn, Facebook, which sometimes Instagram if you, if it's the right format. But so you guys have probably seen us livestream and YouTube obviously, right? Simultaneously. But I will say we do get the most live views on X. So it is something where, you know, they take video very seriously on this platform. Obviously with all the changes they've implemented in recent years, video has become more prevalent on the platform. So yeah, it works really well for us. You know, we were early to kind of live streaming back in 2020. I think some people have a misconception of like, okay, like live streaming has either become the norm, so it's kind of like a throwaway or It's something that doesn't work anymore, right? So people don't take the time to either do it or train their teams up on how to do it. Is, you know, there's a little bit of technicality stuff you have to learn to livestream all these things and like, are we doing it simultaneously? Who moderates what? You've got to, you know, switch back and forth to moderate questions on the livestream, keep an eye on, like, it is an audience, right? And so I always think it's good to reshare here and, you know, great to see such positive results on the livestream. Lots of encouragement with our partners. I know, Waylon, you had sent screenshots to your sponsors immediately, right? Like their last reviews, I guess what were, what was their reactions? Just so that folks kind of understand, you know, that the above and beyond impact, right? Like obviously this is something that they're, they're probably more sponsoring for leads, but just to get, you know, those extra eyeballs. Yeah. What has it kind of meant?
Well, yeah, like, I mean, I sent them yesterday and the numbers are way higher today and they were already, I think like when I sent to the Stiki team or Stiki and the Runway team, they were only at only at 3,000 views. Now we're at 17,000.
I mean, 3,000 is a lot.
No, that's what I mean. It is a lot. It's a lot more than I expected. That's a huge audience. Like, you think about a 3,000-person room, like, that's a big room. That's a fair-sized theater. And then we're at 17,000. Like, that's basically an arena, right? So yeah, yeah, there was a problem. We were happy at 3,000. So I'm definitely going to be following up to let them know. I guess one question for people watching this, maybe, are people able to get the decks from, like, if they didn't sign up already, can they go sign up now? Like, how do people get access? Because, like, the prompts and stuff like that were really cool, and I think a lot of people would love to see those.
Yeah, that's a great question and call out for the audience. Yeah, we, we're, we're posting them all on Saastr's SlideShare. I know we're, like, the only people still using SlideShare. We will email it around to folks. If you were an attendee, right, we'll email you all the links so that you have it handy, or if you signed up. And then just generally, we are gonna write up each of these sessions and put it on sas.com with the slides in there. So it'll probably be, that's its most digestible format, I would say. You know, we write it up, it's all SEO optimized, it's all outlined like a playbook. So that's the easiest way to digest it. But yeah, that's how you can get it now. And then obviously on YouTube, yeah, there's, there's, you could screenshot it if you really want something now. But yeah, that's, that's the best way to get it. But yeah. It's just going back to kind of like, you know, the theme of exposure. Yeah, I think, you know, it's something I always try and explain to sponsors of like, okay, like, it's again, in-person and digital, there's so many commonalities and also differences and like benefits to one versus another. Obviously, we do it all at DASDR because you kind of have to do everything. I would say, I'm like, I wouldn't pick one or the other. No, a lot of these partners are going to be either at Europa or both the Europa event and the SaaStr Annual. Like for a fact, like each of these sponsors is also sponsoring the in-person component, right? So I'm glad to see that that has taken traction as a pattern with, you know, one of our partners of doing both things. Because I do think, you know, there's benefits to both, right? Like to your point, you don't have to travel for a digital event, but also like, you know, and like if you had all these people in a room, yeah, 3,000 folks would be like a, you know, huge stage, 17,000 folks would be an arena. You'd be like, wow, that is such an amazing impact, right? So I always try and tell people to imagine each of these viewers like as filling an actual seat in an in-person event. Like, that's a good way to just visualize it, right? But also, you know, it's a digital event. So you do have to do a bit more follow-up with these folks because you didn't get to actually meet them in person, right? That's the magic of being in person is anyone that you're in the audience and talking to, you can then actually talk to after. So we try and recreate that a little bit using like, you know, more of the Zoom meeting format versus the webinar, which we used to use. So now the meetings is at least, you know, people can come ask questions face to face with the speakers in real time, which I think is quite nice. But yeah, all that to say, you know, all these extra eyeballs are impactful. And yeah, live streaming for us has always been one of those things where, you know, depending on the topic and, you know, kind of perceived value to the platform, we've seen different numbers of varying degrees of like, yeah, you know, a couple thousand would still be good, but as you've seen overnight, like more people are watching this on the replays, probably because everyone's watching everything AI right now. But which we, you know, we kind of thought, but you never know for sure until you get— until you get there. So yeah, it's, it's nice to see that it still has that longevity because I do feel like folks have kind of either they roll their eyes or they kind of grumble when they're like, but it's a digital event. I'm like, no, like if you, if you actually do it the right way and invest just, it's very impactful, right? And there was a lot of times, I know personally, like we did a lot of, like we did a couple rounds of actual like speaker content reviews and like revisions. And, you know, these were, there were some last minute calls of like, okay, can we swap this for this? What about, you know, talking about this theme or incorporating something else? And so obviously that's all paid off because AI Day was like a huge digital event success. So yeah, any Any other thoughts there, Waylon, either on like the partners, sponsors, or just AI Day overall?
Well, one, it's like, I hope, like, I'd love to see us, I hope we do more because we certainly way over-delivered on what we promised for sponsors. We definitely did.
Right?
Like, you always, that's like, you always want it to be the case, but like, we really massively over-delivered there. But I think the quality thing, you know, having a dedicated speaker team that really has a high bar in terms of like what makes it on. Is really what makes SaaStr events both in person and at home stand out. And it's, you know, even if you're, you know, spending a lot of money at a SaaStr event and you've got stage time, it's not just you go on stage and talk whatever you want. Like the content bar is the same. And I think that's why, you know, people look to SaaStr for thought leadership first.
Yeah. That is such a great point. I think too, like the other thing I'll kind of close on on AI Day and then we'll talk about what's next for us, which is, you know, you're— well, there's Workshop Wednesdays and these in between because we do these every week. But, you know, I'll talk about what's the next major event for us. But yeah, I think just one thing kind of to wrap on for AI Day, and I know we did this, we broke our cardinal sin of, you know, we make all of our content usually do slides and we didn't do slides for today because we just wanted to like kind of riff on our final thoughts on AI Day. So we'll, we'll, we'll make them more formal and we'll, we'll, we'll turn it into a SaaS post of all of our learnings. But yeah, I think the last thing I'll wrap on is, yeah, to that point, right? Like a lot of our sponsors, like I said, all the sponsors of AI Day that were participating as a sponsor are also sponsors of our in-person events, whether it's the annual, Europa, or both. Right. So great to see folks kind of doubling down on the formats. Good to see, you know, so many people too were able to deliver content on AI. During, you know, AI Day. It was like, you know, not everyone can do that and say, okay, I'm literally going to launch what I'm doing around AI at AI Day, which a few folks did actually. They were like, yeah, this is like hot off the press, like did this for this, which is actually kind of the magic of, you know, what sponsors and partners have done at, you know, past SaaSRe annuals, past SaaSRe Europas. We've had people launch like research reports, case studies, new products, new features, rebrands, like, you know, that's part of the magic of things that people do in person. So great to see people did that still at a digital event. And yeah, for all of our partners, right, like just to get maybe into the technical weeds for 60 seconds and then we'll go back is yeah, so a lot of these partners, you know, did a session with us, worked with our speaker team and today are getting, you know, a fair amount of the leads from it. So that is, you know, not only do they get all these eyeballs, they get those leads, which I think is just crazy to see because a lot of them actually ended up with hundreds. Like we always ballpark low of like, you know, We'll see how reg and signups go. Like we never try and overpromise of like, okay, we can guarantee you XYZ amount of, you know, leads. It's the same thing we do with in-person, right? We can kind of guide them on if you do activations, you can get more. Like if you do content, you can get like, we kind of guide people to how to maximize it. But I think just to see how many signups there were just naturally from, you know, attendees picking their sessions was really great to see. So yeah. We— it was something that was a great success in that standpoint, I think, for both SAS and its partners of like, you know, we were able to deliver that for them without it being too forced, right? Of like, okay, we've got to kind of go back and make sure people either, you know, like do a second wave or something. It's like, you know, it was all kind of like naturally flowing with how folks signed up and picked sessions and the agenda. It's also why, you know, I know we had a few folks who came in last minute and wanted to sponsor AI Day that we couldn't accommodate. We do have certain processes, right, that help us kind of make sure we can maximize that time to lead value. So with that, maybe that's a good transition of, you know, the things we're gonna do next. Because that time to lead value is very prevalent in maybe even more so for in-person than it is for digital, right? With digital, you can get away with doing a few things last minute that you wouldn't otherwise be able to for an in-person event. And so, yeah, again, we are We're still gonna continue doing Workshop Wednesdays every Wednesday. It's just yesterday we're, we're instead of Workshop Wednesday, we did AI Day, which was like, you know, 12 workshops at once. We do these every Thursday as well, you know, our Saastr Insider Series. And you know, we do the podcast in between all of our newsletters and all that. So what's next in major on our Saastr event schedule? If you're like, oh man, how did those people get AI Day? Because now I want something similar. Well, you know, we do have two big in-person events coming up this year. Again, hopefully AI Day is a good sample case of that time to lead value. SaaS Europa is coming up in just a couple months. I would say again, on that time to lead, it's not too late to get involved. We are, however, though, in April, like starting to launch everything with sponsors, right? So people are going to start picking their boots, they're going to start working on their content, they're going to start working on like their on-site presence. And so that That's, I think, the most optimal time to still get the maximum value out of it. Not to say you couldn't do it last minute, but again, being more prepared, I think, always helps. So that'll be the 4th and 5th in London at the Tobacco Docks. That's our next major event. And then, you know, the, the big daddy, if you will, is the SaaStr Annual. This is the 10th SaaStr Annual. It's in the Bay Area. It's at the San Mateo County Event Center. It's a massive, massive 40-acre campus. We will be live streaming. We will have some digital components at both of these events like we did, you know, AI day. We'll take certain pieces, kind of repeat them at the in-person events. And so yeah, we don't have to belabor it too much, but that is what's next for us. That is, you know, what's top of mind for us. We're going to continue on this AI thread though. You know, we're going to do an AI summit at SaaStr Annual. There is already an AI track at Europa. So the agenda is live. So if you haven't seen it, you can go on the SaaStr Europa website. There's a whole track in like the first day, half afternoon that is literally all AI content, like contextual deep, like lots of folks coming to that one. Lots of really great speakers that are gonna be, yeah, OpenAI is coming to that one chatting about AI. So lots of great folks that are coming from the States to Europa to talk about AI. So that is exciting and also a good segue. Anything you wanna add here, Waylon, about, you know, obviously we'll, we'll deep dive in the next couple weeks on, you know, Europa and all that and annual and AI Summit at annual. But yeah, anything you want to touch on now for the in-person events?
Yeah, a couple things. So although Europa is coming up, there's still like, if it is something that you want to do, there's definitely still time. One of the great things about SaaStr is everything is turnkey at our events. So, you know, basically the pre-event lift on your end is basically submitting booth graphics. We print, build the booths. You just show up on site and be ready to make an impact. We also do, you know, training for your team about how to maximize the impact that you have at the event, you know, increase your ROI, obviously. And then we're also there to support you on site. So it is something where if it is something you think could be valuable for you, it's definitely not too late. And then content-wise, yeah, I think, you know, if the views on the AI content are any indication, like it's some really great content that you're going to want to see. So whether you want to come as a sponsor, as an attendee, it's going to be a great event.
Yeah. Really great points there. Yeah, I know it's the end of the quarter, so again, we'll try and keep this one briefer than we normally would. Hopefully you guys are all, you know, having good luck closing those last-minute deals. I know we're going to try and go do that for the rest of our day after this. But yeah, folks want to get in touch with Waylon. What's the best way to do that?
Yeah, you can reach me on LinkedIn, Waylon McGill, or on email, waylon@saastrinc.com. That's W-A-Y-L-O-N-M-A-K-I-L-L. Lon@saastrinc.com.
Awesome. And as always, I am, I'm still ai@saastrinc.com. Those are just initials, but you know, also any AI questions you can funnel there, that's fine. I'm trying all the apps, so send it all to me. That's totally fine. I did get a lot of them in the last week, so I may not get back to you right away. But if you have an AI app you want Saastr to try, I'm the person trying them at Saastr, so you can still send that to me. Yeah. So yeah, that's, that's what we'll wrap on. Thanks everyone who came to AI Day yesterday and participated. Was great to catch up with the community, especially on AI. And then yeah, we will see you next week, not only for this one every Thursday, but we'll see you for Workshop Wednesday as well. And hope you guys have a nice long holiday. And if you're on spring break, enjoy. And we will see you soon.
Bye everyone.
Bye folks.
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