YC posted a list of top alumni companies by valuation, as of October 2018. You can see the full list at https://ycombinator.com/topcompanies.

Here’s a Q&A with Cai GoGwilt and Jason Boehmig, the founders of Ironclad, one of the companies featured on the list.


What does Ironclad do?

Ironclad makes software for legal teams to help them make contracts faster and track the key information in them automatically. Our solution brings fragmented contract processes together into a centralized system of record. We do this by integrating with the systems that our customers use in their day-to-day business, like cloud storage, e-signature, CRM (e.g., Salesforce), and other solutions.

By automating contracting processes and extracting intelligence from contracts, Ironclad lets legal teams at companies like Dropbox, HotelTonight, Procore, and Glassdoor focus on legal work, rather than paperwork.

How many employees does Ironclad have?

Right now we’re around 50 employees, with plans to double that in our next year.

How many founders?

There are two of us. Jason, who previously practiced corporate law at Fenwick & West, and Cai, who was previously a software engineer at Palantir and who studied CS at MIT.

What is your most impressive recent product milestone?

We recently released Blueprint, which lets our customers set up their own contract workflows on our system. It’s important because the rest of our industry relies on expensive and time-consuming consultants to set up their implementations, which can take months or years. Blueprint allows our customers to be up and running in minutes, without having to write a single line of code.

What is the larger impact / societal impact of your product in the space you work within?

Contracts are foundational to society. The fact that we still make them in a very old-school way, with a mix of non-specialized systems, really slows down the pace of business. If we’re able to transform that across the world in the same way we already do for our customers, the results would be enormous. Businesses can transact more efficiently. Even more importantly, they can actually know what’s in the legal agreements they are creating. And, they can also use that data in new and interesting ways. We’re excited to have the chance to play a role in how contracts, which have been around for millenia, will evolve into the digital age.

What’s an interesting element of Ironclad’s company culture?

We’re really proud of our culture. We have four key values: Intent – we want to be thoughtful in everything we do and have an ownership mentality; Empathy – we want to care more about people than is common, both our team and our customers, and be able to step into one another’s shoes; Drive – we want to be the best at what we do and hold each other to the highest standard of excellence; and finally, Integrity – we want to not only win, but win the right way.

Another thing we’re proud of is our team’s diversity – we’re 50% women and have a wide variety of racial and cultural backgrounds. We think it’s important to also have diversity of thought. Our team is super quirky and smart. We eat lunch together every day and we love hanging out after work.

Looking back, what motivated you to start Ironclad?

Jason was a practicing attorney, and so was able to see the real problem that businesses have dealing with contracts on a day-to-day basis at his job. Cai was intellectually interested in how to take a smart user (the legal team) and help them scale themselves in the same way he was able to scale himself as a software engineer.

Together, we realized that the landscape of legal software is littered with disjointed tools that might help solve pieces of puzzles, but don’t empower legal teams to make strategic and ultimately transformative business decisions. We wanted to give legal teams a total, holistic solution for contracts.

Is what you’re working on now the original idea or did you pivot?

We’ve been executing on the same vision since we met. It took a lot of faith in the early days, because almost nobody else believed that what we were working on was a good idea. Most people said that legal teams were a bad audience, that they wouldn’t adopt technology, and that they would be a bad buyer. But we wanted to serve them, and it’s paid off. We’ve looked back at our YC application periodically, and it’s really cool to see how we have the same mission we began with.

Were there moments where you thought the company might die? Describe one of those and anything you learned from it.

One of the biggest decisions we made early on was not to focus on the law firm market. Who knows whether it was the right one, but we’ve been very happy being laser-focused on the corporate legal team market. That focus has helped us achieve clarity and purpose with our product that is unique in the market.

What was a particularly important insight you had about your market that made your product work?

Early on, we received advice to focus on a single vertical/type of contracts (for example, sales contracts), but because Jason was a corporate lawyer he realized that actually, all contracts go through the same steps. For that reason, we committed to building a system that would be helpful to centralizing every type of contract that a company might encounter. That insight has made it possible for Ironclad to be the only platform you need, regardless of contract-type.

What’s one piece of advice you’d share with a young founder?

Asking for help is a superpower. You may be the most intelligent, talented, and skilled person in the world, but you’re going to need help on your journey. Get good at asking for it!