Three things Ironclad did well from seed to A. Or, Ironclad: layin’ down the law.

Kevin Webb
Webb Investment Network
3 min readAug 9, 2017

As you might have seen last week, Ironclad formally announced its Series A raise with Accel, and we couldn’t be happier to see this team hit this milestone. Since 2015, Jason and Cai have been quietly building mission critical software for corporate legal teams.

In case it’s helpful to future entrepreneurs, I wanted to take this moment to highlight and celebrate a few things that this team has done very well over the past two years:

  • Build Community. Within a few months after YC, Ironclad started pulling in a trusted pool of General Counsels across the Bay to gather feedback on their offering, and to get them involved in regular events. Every two weeks, Ironclad has a Friday evening talk with legal experts. These events are interesting, fun, and filled with good people, and they lead directly to landing new hires and customers. In legal experts, Ironclad has found a network of passionate, talented people who are curious and generous with their time, and who don’t have as many opportunities to connect with one another as their peers in other departments like engineering, product, or marketing. These relationships have proven crucial in Ironclad’s progression from supporting early startups to landing enterprise customers, and will continue to serve the company well.
  • Move Up Market: When we first met Jason and Cai, their customer base was made up almost entirely of small deployments at small startups. This enabled them to prove their contract management system could work across many different customers, while constraining the range of documents they had to support to the handful that small startups needed most (e.g., SAFEs). Watching the monthly updates, though, there were two clear trends as their software grew more robust — first, the slow trickling of large enterprises signing up, and second, that the customers who really started using their offering tended to expand their deployments over time. Ironclad was helping these companies to view contract management as a process that can be streamlined and bulletproofed. And legal departments found that with Ironclad, they could keep up with their businesses’ rapid growth — without adding any headcount.
  • Communicate: There were a few months when revenue remained small, and monthly growth in total number of customers, revenue, and engagement was close to flat. Often these points can be where a founder removes metrics, swaps them for artificial ones, or worse, stops sending updates altogether. Instead, Jason and Cai shared everything, and they stayed focused on serving their customers. With investors, they sought critical feedback and customer introductions, and they highlighted individuals every month who were particularly helpful (which tends to make us investors work even harder to get in the next month’s shoutouts). Over the subsequent months of updates, it became clear that their hard work was really paying off.

Building companies that last is incredibly hard, and Ironclad still has a very long road ahead of it (we hope!). But I’d just like to commend this team for getting to this point in such a thoughtful, deliberate way.

(And if you know someone who might be interested in optimizing their legal org, or who gets excited about the intersection of software, AI, and law, please direct them to https://ironcladapp.com/).

Also special thank you to my colleague Jeremy for suggesting a slew of historical ironclad ship puns for this post’s title: “Ironclad: Steaming ahead,” “Ironclad: taking broadsides since 2015,” “Ironclad: bulletproofing your contract management.”

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Kevin Webb
Webb Investment Network

Previously investing things @winfunding, now studying sustainability science at Columbia. Interested in building a world for people & diverse, rich ecosystems.