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Meet Toby Willcocks, Ironclad Legal Engineer

October 2, 2018 5 min read

Toby Willcocks was Ironclad’s first business hire. Over the past two and a half years, he’s worn a number of different hats at the company and has helped dozens of clients implement Ironclad.

Like all Legal Engineers, Toby is an expert in both legal workflows and solution design: he works with clients to figure out how Ironclad can best be implemented, then oversees workflow designs, systems integrations, and roll-out from beginning to end.

In this interview, Toby discusses:

  • Why he chose Ironclad over a more traditional career in law, as well as the pros and cons of entrepreneurship;
  • How his role at Ironclad has changed over time, and what he expects moving forward; and
  • Why Blueprint, Ironclad’s contract automation tool, will enable commercial legal teams to rethink their existing contract processes and become dramatically more efficient

You joined in 2015 as one of Ironclad’s first employees. How did you find out about the company and why did you decide to join?

Ironclad combines my two strengths–law and entrepreneurship. I’ve never worked as a lawyer, but I studied law as an undergraduate at Oxford and received an LLM from Harvard Law School.

One thing I noticed during my internships at law firms was that the industry is filled with very bright people working under a structure that’s often archaic. That, combined with the rigid career trajectories in law, led me to look for something more entrepreneurial.

When I found out about Ironclad on TechCrunch, I cold-emailed Jason (our CEO), and told him I wanted to help out any way I could- even if that meant working for free! I flew out to California, spent a week with the team, and have been here ever since. At the time, Ironclad didn’t have anyone on the business side, so I was the first business hire.

How has your role changed since you started?

One of the things I love most about tech companies is that most roles aren’t rigidly defined–that can be daunting, but it gives you the freedom to chart and pursue your own career trajectory. My title hasn’t changed during my time at Ironclad–I started as a Legal Engineer and still hold that position–but my responsibilities have evolved significantly.

In the early days, any issue that wasn’t Product- or Engineering-related came to me. My goal back then was to do whatever it took to help the company grow. A lot of times, that meant acquiring new skills quickly and learning on the fly. One of the great things about working at a company like this is that you’re forced to grow quickly and can take total ownership over your successes and failures. On the other hand, you might have less guidance or mentorship than you would at, say, a law firm–that’s definitely part of the trade-off.

As our company and product have matured, my role has shifted from that of the all-around problem-solver to more of a thought partner for our clients. Back then, I was mainly concerned with getting the Ironclad system up and running. Today, I’m helping legal teams think through their business processes and working with them to identify their most important long-term goals.

There are a few different players in the contract management space. What differentiates Ironclad from its competitors?

I think a lot of things separate us from competitors, but I’ll focus on two for now: our implementation model and our product roadmap.

We implement Ironclad by sending teams of Customer Success managers and Legal Engineers to work on-site with clients. We have a “bias toward onsite” mentality, meaning we take every chance we can to meet with actual Ironclad stakeholders and users. That’s a key distinction, right off the bat. This is uncommon; typically, contract management vendors “throw software over the fence,” meaning they offer limited support to the client after installation. Just as important as our implementation model is the quality of our implementation teams. When you work with Ironclad, you get world-class consultants, lawyers, and account managers coming onsite and making sure that every detail of implementation is optimized–from workflow design to user training. Not only does that mitigate any implementation risk, it gives you access to some of the brightest minds in legal operations and technology.

The second differentiator I’ll highlight is the product roadmap. This actually flows from the implementation model I described. As they work with clients, our Legal Engineers provide a steady supply of feedback to our Product team. What’s working? What’s not? Are there any trends in feature requests coming from customers? In contrast with most other contract management solutions, Ironclad’s product roadmap is a result of years of iteration with customers. It reflects what we’ve learned from working with customers as well as emerging trends in the legal operations space. The best example of this is Blueprint, a self-service contract automation tool that Ironclad is rolling out this fall. We didn’t just decide to build Blueprint one day. We built it based on the lessons we learned from dozens of Ironclad implementations, and from hearing the same pain points faced by in-house counsel across a range of industries.

Tell me more about Blueprint–how and why did the Ironclad team decide to build a self-service contract automation tool?

Blueprint is the next step in our product evolution, but it’s also a result of lessons we’ve learned over time. If we’d tried to build a self-serve contract engine from day one, it would have been impossible. We really needed to learn what a good workflow engine looks like first. What are the approval processes that trip up contract teams? How do different departments prefer to communicate with each other? These are all questions we weren’t sure about before we went out in the field.

What Blueprint allows in-house counsel to do is to use a point-and-click system to automate things like NDAs and other simple agreements. Previously, this required the help of an Ironclad legal engineer. With other solutions, it’s basically impossible. It’s hard to overstate the efficiency gains that Blueprint will enable. Workflows that used to take weeks to automate will now take days. We expect that, as in-house counsel automate more and more workflows, they’ll be able to shift their time to higher-value tasks. In that sense, Blueprint will help clients and Legal Engineers move up the value chain and spend more of their time optimizing complex workflows–things like vendor agreements and offer letters, for example.

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What would you say to prospective hires looking to join the Ironclad team?

If you’re looking for a mission-oriented company, this is the place to be. The thing that has impressed me the most in my time here is that the mission of the company has always remained the same: to bring a new technology platform and way of thinking to an industry defined by inertia. We’re not just building a tool and handing it over to customers. We’re partnering with them to change the way they approach their work. For many customers, thinking through long-term goals and business process changes is a new and exciting experience, since it means they can accomplish more with the teams they already have.

The flip side of that is that Ironclad will be challenging–it will force you to think creatively, become an expert on legal technology and operations, and partner with customers to better define goals and accountability metrics. If that sounds exciting to you, reach out to me at I’d love to hear from you!

Want to work with Toby? We’re hiring! For more perspectives on life at Ironclad, check out our previous interviews with Jen Paau (COO) and Damon Mino (VP of Sales).

Ironclad is an end-to-end contract management and workflow automation platform. By automating contracting processes and extracting intelligence from contracts, Ironclad lets legal teams focus on legal work, rather than paperwork. See what we’re building today. 

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Stacey Wang is the Director of Product Marketing at Ironclad. Before Ironclad, she worked in Business Development at Palantir Technologies, and before that, she was a litigator at Orrick, Herrington & Sutcliffe. She is a California-licensed attorney and graduate of Harvard Law School.