Todd Jackson’s Post

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Partner at First Round Capital

AI legal startups are a thing in 2024. But as Ironclad's Jason Boehmig puts it, “nobody was trying to buy an AI legal assistant back in 2015.” As we were developing First Round Capital's PMF Method, we learned so much from their journey — grateful Jason took the time to share insights. 🙏 My takeaways below: 🔬 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 several years of iteration. We had to figure out what we could peel off into a repeatable, discrete software product. We quickly realized the interesting part of the problem was in repeatable business transactions — NDAs, sales, partnership and employment 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. Turns out it’s a Contract Lifecycle Management platform that helps enterprise companies create and manage legal contracts. So of course I wrote back, ‘𝘞𝘦 𝘢𝘳𝘦 𝘥𝘦𝘧𝘪𝘯𝘪𝘵𝘦𝘭𝘺 𝘢 𝘊𝘓𝘔, 𝘸𝘦 𝘸𝘰𝘶𝘭𝘥 𝘭𝘰𝘷𝘦 𝘵𝘰 𝘤𝘰𝘮𝘦 𝘥𝘦𝘮𝘰 𝘰𝘶𝘳 𝘊𝘓𝘔 𝘧𝘰𝘳 𝘺𝘰𝘶.’ But we hadn't put a lot of thought into dealing with contracts afterwards. 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 GoGwilt, and said, 'By the way, we have 3 hours to build a repository feature.' We took the train from SF to San Jose and he built the first version, which we demoed live at the end of the train ride. This customer was in an evaluation cycle with 12 other CLMs solutions, but they loved the demo and we eventually won. After that, we changed our messaging. That's still our flagship product to this day. 📚 𝗙𝗼𝘂𝗻𝗱𝗲𝗿-𝗹𝗲𝗱 𝘀𝗮𝗹𝗲𝘀 𝗶𝘀 𝗹𝗲𝗮𝗿𝗻𝗮𝗯𝗹𝗲 I was impressed to learn that Jason still sends cold outreach himself. But founder-led sales wasn't natural. “A misconception I had was that the cartoon character who's slapping everyone on the back and is a total extrovert is the best salesperson. It's actually the person who's almost an engineer in their mindset — super methodical, sends great follow ups, could be shy. It's a very learnable skill.” Tons more of Jason's and other founders' advice for every stage of PMF in our new essay (link in the comments!)

Todd Jackson

Partner at First Round Capital

2mo

Listen to other $1B+ B2B founders share PMF advice here: https://youtu.be/iD1vQ4tHhO4?si=yxKqpipto7OvGMAP Prefer to read? Our new essay lays out our PMF Framework in full: https://pmf.firstround.com/levels If you’re a B2B founder interested in taking a more rigorous approach to finding product-market fit, consider applying for PMF Method — application deadline is 5/7: https://pmf.firstround.com/

Impressive insights! To gain even more traction, have you explored leveraging machine learning algorithms to dynamically segment and target your content? ManyMangoes consistently achieves higher engagement by implementing granular audience segmentation using AI.

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Dakotah Rice

Co-Founder @ TatchAI | ex-Coatue, Carlyle, Goldman, & HBS | Forbes 30u30

2mo

The shifting messaging is CRITICAL in selling to industries with a ton of sensitive data. You have to find frameworks that people understand and learn that even though you think its cool to say things like "AI-native, AI-first, autonomous" it can scare customers. Thanks for sharing. This is important

Colleen Krieger

Marketing Advisor & Strategist | Fractional CMO | Founder, Superbloom Strategies | ex-Capital One, Edelman

2mo

Couldn’t agree more about expanding an existing category! It’s easy to burn calories trying to create a new category. But often that just sets up barriers to your audience being able to choose you.

Sanjay Krishna

Growth @ Coast | MBA @ Kellogg '25 | Ex-Founder/ Operator/ Lawyer

2mo

This is a fantastic series!

Nastasha V.

Strategic Ventures and Advanced Technology Innovation

2mo
Markus Andreasson

Transforming Innovation and Patent Protection with AI | CTO & Co-Founder, Lightbringer | Product Builder

2mo

Love this story. Thanks for sharing!

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Cory Blumenfeld

3x Founder | Results-Driven Startup Operator & Generalist | Always Building...

2mo

Love these insights! It's always fascinating to hear about the twists and turns in a startup's journey. Sounds like Ironclad found its niche through some creative problem-solving!

Javier Rincon 💡

Product Leader | Build Product-Market Fit at startups | Lean

2mo

Great case study thanks for sharing Todd Jackson!

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