AI legal startups are a thing in 2024.
But as
@ironclad_inc’s
@jboehmig puts it, “nobody was trying to buy an AI legal assistant back in 2015.”
Ironclad has one of the most interesting and underexplored stories out there IMO. As we were developing
@firstround's PMF Method, we learned so much from their journey — super grateful Jason took the time to share his insights for other builders. 🙏
Here were a few of my takeaways:
🔬 Zoom in to find focus
“It was actually fairly easy to sign up early customers — what was difficult was finding a product that could address that market. That took us several years of iteration. We had to try to figure out what pieces we could peel off into a repeatable, discrete software product.
We quickly realized the really interesting part of the problem was in repeatable business transactions — sales agreements, employment agreements, NDAs licensing agreements, partnership agreements. A lot of our competitors tried to do everything that corporate legal teams do. But we were only doing the contract part.”
📣 Expand an existing category (with an existing buying cycle)
But the initial AI legal assistant positioning wasn’t resonating. I’ve talked to 100s of founders about PMF and the story of how Ironclad got unstuck is one of the wildest ones I’ve heard.
“100% of the time I had to explain what an AI legal assistant was. We had a hello@ironclad.ai email on our site. One day I got a one-liner message that said, ‘Hello, are you a CLM?’ I was so close to hitting archive, but it was from someone at a publicly traded company. But what was a CLM?
Turns out it’s a Contract Lifecycle Management platform that helps enterprise companies create and manage their legal contracts. By that definition, we were. So of course I wrote back, ‘Yes, we are definitely a CLM, we would love to come demo our CLM for you.’
But while we were really great at creating contracts with our AI legal assistant product, we hadn't put a lot of thought into how you deal with contracts afterwards, with a feature called a repository. And so we had set up this demo with the legal team from this publicly traded company, and I turned to my co-founder Cai, and said, ‘By the way, we have 3 hours to build a repository.’ We took the train from SF to San Jose and he built the first version of a repository, which we demoed live at the end of the train ride.
This customer was in a CLM evaluation cycle that had 12 other solutions in it, but they loved the demo. So we went and actually built the full product, and we won. And after that, of course, we changed our messaging. We got serious about building CLM functionality and that's our flagship product to this day.
There were lots of people out there trying to buy a CLM so we just got to participate in a lot of buying cycles, but with the AI legal assistant buying cycle, we had to create every one of those.”
👥 Artificially constrain the buyer and build community early
“One of the things that we did which was really helpful in hindsight was we artificially constrained the buyer we were going after. Once we decided to make the shift to enterprise, instead of trying to address the whole US market or the whole global market, we decided we only cared about being the number one CLM in SoMa. We got a list of every company that could use the CLM in SoMa and got intros to them — it just provided a ton of focus for us.
It's how we also stumbled into doing community. We would host these community dinners and if you were a general counsel of a company based in SoMa, you probably knew other people that were coming to them. We just started to get this buzz of ‘Are you going to the Ironclad thing tonight?’
There's a ton of value if you can discover a part of the organization that no one cares about, and connect that part of the organization to a larger business problem.”
📚 Founder-led sales is learnable
I was impressed to learn that Jason still sends cold outreach himself to this day. But founder-led sales didn’t come naturally.
“A misconception I had about early-stage startups was that the cartoon character salesperson who's slapping everyone on the back and is a total extrovert is the best salesperson. And it's actually the person who's almost like an engineer in their mindset — super methodical, sends great follow ups, could be very shy. It's a very learnable skill.”