9 takeaways from SaaStr

First time at SaaStr. Not sure why it took me this long—but I immediately felt at home. If you're reading this in San Mateo, I’m on the AI demo stage at 10am today (Thursday) for Skyp.ai. Come by.

Part of feeling at home was thanks to Audine and the team at Maxio, who recognized me after I was a guest on their CEO’s podcast a while back. Always fun to meet great people in person you’ve only worked with virtually.

SaaStr is yet another reminder that conferences are phenomenal for customer development and, depending on what you sell, meeting prospects. If you’re a founder and there’s a good conference that has your ICP in attendance–go! The conversations you’ll have in 2-3 hours of walking the floor are far, far better than anything you could get almost any other way. Even better if you can be a speaker. Did I mention I was speaking pretty much right now?

I had a mix of observations today, and couldn’t string them together. So this post is in two parts. First, takeaways from SaaStr–because everyone loves a list. I wouldn’t describe any as “news” but perhaps they reinforce thoughts you’ve already been having or trends you’ve been seeing elsewhere. Part two is about competing, which at least from my perspective was on display today.

9 takeaways from SaaStr 2025

Everyone loves a good list, so list it shall be.

1. AI is hotter than mobile at Mobile World Congress in 2011

   AI is very, very in. There’s a whole stage for AI. Most of all presentations are about AI. Integrating it into your app or enterprise. Building it. Securing it. Managing it. Attendees are talking about AI organically. SaaStr even got SaaStr.ai.

2. Some AI demos were incredible

   There were many. Here are two. Getbreakout.ai demo’d live personalized demos built by AI for current live visitors in real time on your website. Sounds insane but seen live it was awesome. Dobs.ai will audit an enterprises contracts and invoices to find mistakes, and save money. Like that 10% discount that was in the agreement–but not in the latest invoice. This used to be a juicy McKinsey project that saved you $15 million. Now, it’s software that saves you $15 million. Wonder which is higher ROI?

3. AI is not a silver bullet for GTM

   Just because it is AI doesn’t make it easy to sell (or a good business). Not calling anyone out, but there were some demos that could have benefited from some marketing and messaging help. ChatGPT can’t fix everything, I guess.

4. AI growth rates are shocking.

   One AI founder casually mentioned that her company had reached $2 million in ARR–7 months in. I think the rate speaks to both how fast one can build today using AI tools (cursor, bolt, etc.) and also how much demand there is for AI-based solutions. Done well it really is magical.

5. Branding matters. 

   Artisans, a Skyp competitor, is everywhere (and I’m sure, paying dearly for it–on which more later). But great branding stands out anywhere. Adopt, which makes AI agents, had a cute dog as a mascot; that kind of clever touch was not lost on me, at least.

6. Most people have no idea about AI.

   Most attendees were uninformed on AI. These were CEOs of 100-1,000 person companies, entrepreneurs and marketers. While there were people building extremely advanced AI apps, most people were still in the dugout, thinking about taking the field.

7. Wells Fargos are emerging

   The vendors to AI builders are emerging. Sure, there’s the cloud and compute providers. But that’s not a small startup’s game. One example: getbasalt.ai helps AI developers analyze prompts, to see which are better so they can tune their product. This was a problem my cofounder and I were wrangling this morning. I had no idea anyone else had been thinking about this–let alone building it.

8. Competition is next to you.

   If one company can succeed in a market, so can others. Rippling was next to Remote. There were several subscription billing companies next to each other. They all seemed to be getting a lot of traffic.

9. Great hospitality is easily overlooked.

   Great hospitality is almost invisible. I didn’t notice it–until an events marketer pointed it out. There were no lines– at bars, lunch, or even to get badges. Everything looked great–because the conference set the booths up for the exhibitors, there’s a welcome uniformity to it all. It’s the little things. And big ones. Well done.

Big markets and competition

As I mentioned, competition is in your face at a conference like SaaStr. One founder friend I ran into asked how Skyp was going to succeed in a crowded space. Another AI founder shared that he felt like he needed to raise because others in his market had raised a lot of money and he was afraid of falling behind.

The answer to both was: Artisans. A Skyp competitor, Artisans was one of three diamond sponsors, alongside Google and Rippling. They’ve raised ~$36M, and spent a meaningful chunk making sure attendees had heard of them. Great brand presence.

The thing is, Artisans is raising awareness for the category. And Skyp.ai benefits from that awareness. It is not a winner-take-all market; some people will like our product more than theirs and vice versa. Meanwhile, my marketing budget is $0 and we have sold 0% of our company to fund marketing. Pretty good deal, if you ask me. I hope Artisans keeps it up.

Small markets and competition

I was fortunate to catch up with my friend Melissa Moody, who has started a group for executive women called Wednesday Women. Highly recommend. Of course, there’s already Chief–which has a strong following and is quite, quite large. I’m not sure what this market would be called–professional women’s networking?–but what is clear is that Chief has blazed a trail, done things a certain way, and some women wanted something different. Wednesday Women grew organically, and is still growing rapidly.

When someone asked her what she did, she could explain it relative to Chief–because Chief has done a tremendous job of marketing itself. And while a lot of what Wednesday Women does is at no cost, you can pay for a membership–which she can easily and unapologetically justify the price of (it is much less than Chief).

I bring it up both because it’s cool (if you want to know more–reply, I’ll connect you) and because it shows that even if a company entered a not enormous market before you, there might still be room for a different approach. And, it might be easier to be second to market.

That demo

By the time you’ve read this far, I’m probably done demo’ing. If there’s quality footage, I’ll share it out in next week’s newsletter, or if you’re curious just reply. Always happy to set up a 1:1 demo if you like (here).

Don’t let big names in big markets intimidate you. If they’re spending to educate the market, that’s your tailwind. If you're behind the leader, you're not losing—you’re drafting. It’s how you win in the long run.

Skyp has almost 50 companies on the waitlist! Grab your spot now. We’re about to launch, going in batches of 5-10, and would love to work with you.