Notes from SaaStr 2025

And my review of Walter Isaacson's biography on Benajamin Franklin

Last week I went to SaaStr in San Mateo. On a spur of the whim moment, I bought a conference pass on a Black Friday deal. Overall it was a great event to meet other founders and share conversations and I had some notes from the conference I wanted to just write down.

The Winner of SaaStr 2025: Go-to-Market + AI

There were a lot of common themes across the conference. I met with at least five people running accounting AI agencies, recruiting AI software companies, but the winner for the biggest theme had to be Go-to-Market AI companies.

So many companies were selling tools for go-to-market. AI SDR, AI BDR, AI Email, AI Drip Campaigns, my god it was everywhere. Go-to-market had recently entered the Silicon Valley canon, and it showed widely across SaaStr.

But do these AI products work? I mean in some cases they do, in the way that each vendor or founder I was talking to had a very specific type of product they were selling in tackling go-to-market. There was the prospecting data layer, companies like PeopleDataLabs or Ocean.io that focused on finding email contacts from LinkedIn or lookalike profiles. Then there was Artisan that was building an agentic SDR to run outbound on all your prospects with a very catchy tagline.

Also why isn’t Jennifer Connely suing for likeness?!

Lemkin had a hilarious anecdote how he was having critical bugs with some SaaS company he had spent hundreds of thousands of dollars on over the years, and when he reached out to support, he received an email a day later from a customer success manager that said something like: “Let’s jump on a call dude”. This to him was an example of how AI would disrupt companies that can’t even personalize their experiences in SaaS.

I agree these situations are quite disconnected. There’s that attention to detail that hasn’t been figured out yet because our systems don’t work together and most people haven’t figured out those workflows that combine human + AI elements well enough yet. Can you really sell someone that an AI + human workflow to send 100 personalized emails is better than the same amount of effort to send 1000 mail merge emails without personalized messaging?

It reminded me of the fact that so much of the stuff that needs to be automated is so currently customized. Take for example what’s running through my head: there was this guy from OpenAI who I contacted on LinkedIn but have yet followed up with because he said it wasn’t a good time a few months ago. But I only have his LinkedIn so I have to remember to find his email and send a continual drip campaign customized to what we discussed. But this use case is just one in hundreds of other kinds. Someone else might have replied to my Substack as a great lead that I should follow up with. Or someone else via text.

In some ways, it’s about myself getting more organized. But AI is supposed to solve the disorganization? In my head, all of these companies are selling specific workflows. But like everyone else, I don’t want to pay for a million tools. And I guess my use case is different because I’m a startup founder.

My last thought are it might be worth deconstructing why everyone right now is so obsessed with go-to-market. There are fears that once AI enters here, your only moat that exists is distribution. But we’ll see if this lasts too.

SaaStr: Your First Time Too?

On the first official day, Jason Lemkin at the keynote asked the crowd how many people had been to SaaStr before. I counted <20 people raise their hands out of a crowd of at least 100+. High churn.

Indeed, as I went around the conference and asked the same old boring small talk “Is this your first time at SaaStr?”, almost every single person said it was. The few that mentioned they had been before I met at the happy hours, where they conspicuously also must have forgotten their badge. Turns out, the happy hours after the events, the intimate meeting places for people to actually have conversations, were where most people found value in SaaStr.

But what surprised me was how many founders there were at the event. Many of these founders had an agenda to either talk to customers or raise from VCs. But when I went to the founder <> VC brunch, there was no brunch and also not many VCs to pitch to.

SaaStr overall seemed like a great event if you were like every other YC or growing startup that was building products to sell to other founders. But it was less helpful if you were a founder and looking for companies to sell to. Multiple vendors I talked to said half the people they talked to were founders pitching them, which made me lol.

How Much to Pitch?

There’s an argument to be made that you should be pitching really hard because your vision of the product cannot be 100% easily communicated through your control of the English language. Even if you had a powerpoint slide, you probably can’t communicate 50% of your idea. And so in order to truly get your vision across to another investor or potential hire, you really have to elaborate reality as it is today and paint a truly utopian future that the person on the other side of the table will naturally handicap because they don’t have a direct Neuralink connection to your brain on how your product will re-shape the future and make them tons of money.