Engineering Change: How Cai GoGwilt and Ironclad are Driving Change in the Legal World

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For years, technology developers have focused on streamlining best practices for sales and marketing departments across the country, but the same cannot be said about their legal counterparts. After all, no two contracts are the same, right?

On this episode of IT Visionaries hosted by producer Hilary Giorgi, Cai GoGwilt, the Co-founder and CTO of Ironclad, talks about how his company is helping legal departments across the country operate more cohesively with their business brethren, why he is an advocate of work-life balance, and why recruiting and training the right people makes all the difference.

3 Key Takeaways

  • Ironclad is a platform designed to help legal departments automate and speed up their workflow
  • Contracting is more than a legal problem, it’s a collaboration issue
  • Building a team is about finding the right people that fit with the company’s mission

For an in-depth look at this episode, continue below.


For Cai GoGwilt, Co-founder and CTO of Ironclad, life is always about balance. In an industry dominated by tech leaders who fail to diversify their calendar with things that are not work-related, GoGwilt is the opposite. Instead, electing to spend his weekends playing in an orchestra or in bars and clubs in the greater San Francisco area. GoGwilt joined IT Visionaries to discuss why that life outside work is important to him, how he also got into his role at Ironclad, the importance of work-life balance, the evolution of legal engineering, and why team success always outweighs individual accomplishments.

For the last 20 years, GoGwilt has honed his love for music. On the weekends, he spends his time channeling that passion into his cello.

“Music is my passion, my hobby,” GoGwilt said. “I’ve talked a bit about how cello has really helped me in my work. I don’t think it’s necessarily from the perspective of being a cellist makes you a better engineer, or a better co-founder, as much as playing music I really think helps you be a better collaborator.”

In GoGwilt’s own words, music helps to center him, serving as an escape from the reality of the daily grind that comes with running a company. But it’s those hobbies that he believes help him in his professional life. Even as a high school student, GoGwilt searched for outlets to feed his passions while remaining productive and successful in school.

“What really turned me on to technology on a personal level, as opposed to just my family, was actually programming graphing calculators, TI-83s,” he said. “Assembler language was my first programming language and I built a ton of stuff while I was a kid in school.” 

Since those days of building programs on calculators and cementing his passion for technology and programming, GoGwilt helped establish Ironclad along with co-founder Jason Boehmig. Ironclad is a digital contracting platform, helping modern legal teams execute and control their contracts, with the goal of helping legal teams work in concert with the rest of the business.

“What we’re seeing in legal teams, especially as companies get bigger is they end up needing to diversify and I would say almost fracture in different ways,” GoGwilt said. “Some legal teams are able to actually be business partners, even with the more rudimentary technology that has been built for them. In these cases, we actually see legal teams that are pretty unified and are able to actually protect the company and be a business partner to various other organizations such as sales, marketing, R-and-D — that’s the exception as opposed to the norm.”

Armed with Boehmig’s legal background and GoGwilt’s love and passion for engineering, the two began to notice market inefficiencies with legal teams. While sales and marketing staff were able to deploy numerous forms of technology to streamline their business workflow, the same could not be said for legal teams. 

“Contracting is more than a legal problem, it’s a collaboration problem,” GoGwilt said. “Early on we were kind of figuring out how the contracting process worked and really condensing it down to make sure that it would work for the legal team, but also make the legal team a good partner to the business stakeholders.” 

The result was a first-of-its-kind platform built by GoGwilt’s engineering team specifically for legal purposes.

“This is really technology that’s built and designed by great engineers and for legal purposes,” GoGwilt said. “Really understanding the user, understanding how legal teams work, what legal teams need to do in order to be great business partners has really been the differentiator in terms of ironclads technology and platform.”

So what were some of the biggest challenges facing legal departments? Business has never operated at the pace it does today, and most departments were unable to keep up.

“The thing that helps legal teams a ton when using Ironclad is the fact that Ironclad gives them the power to iterate at the same pace as the rest of their organization,” GoGwilt said. “If you have a contract that takes you six months to change how a contract works [with] the approval process, the different fullbacks, and the template of the contract itself. If it takes you six months to change, you’re going to be behind in terms of the way business goes these days. You need to really be able to change, change business terms on a dime as you discover, and your business model as you try to open a new line of business.”

As a cellist, one of the GoGwilt’s favorite parts of an orchestra is when all the instruments come together to perform a tune. Much like a band, Ironclad builds its engineering department under a similar mindset, where all employees work together for a unified purpose.

“I always recommend to people that they start by building their engineering team with people who care about the user,” GoGwilt said. “I think you want to be selecting people in the organization who truly care about the end-user, who wants to speak to the end-user, who wants to hear it, even if they’re hearing things that aren’t necessarily great.”

As technology continues to streamline business practices, often eliminating jobs in the process, GoGwilt pointed out that technology should not be seen as a villain, but simply as an ally.

“Software plus humans is greater than just software or just humans,” GoGwilt said. “The legal teams that use Ironclad are the ones that are under pressure from their business to innovate and change. Probably because the business of that company is changing around them.” 

So what’s on the horizon for Ironclad and how does a company expand on their already successful product? The number one thing that excites GoGwilt is the community that’s growing around their product and the future of how it can evolve.

“I’m super excited about the community, both because I think that’s a part of the future and part of the answer in terms of spreading excellence and spreading great ideas,” GoGwilt said. “I’ve been so impressed by the in-house legal community and especially kind of the rise of the legal operations community in terms of trying to figure out what is this new world we’re in. what are the new requirements, and pressures that legal teams are facing and how we cope with them.”

To hear the entire discussion, tune into IT Visionaries here.

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Cai GoGwilt, Co-founder and CTO of Ironclad, discusses how his company is helping legal departments automate the contract process and why hiring a good team makes all the difference.

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