Ironclad co-founder and CEO Jason Boehmig (left) and co-founder and CTO Cai GoGwilt (right).
For my final piece of this series on the world of LegalTech, I sat down with Jason Boehmig, CEO of one of the big success stories of LegalTech VC funding. His company, Ironclad, is a contract management and automation platform used by heavy hitters Dropbox, Glassdoor, and others. Boehmig generously gave of his time to share the story of his company’s founding and growth, and, as we spoke, I found myself drawing different lessons from each stage along the way. I’d like to share that story with you, in hopes the lessons apply well to the world of law firm management.
The Value Of Investment
It helps to start out knowing that Jason Boehmig wasn’t the prototypical 25-year-old law school graduate. He began his career on Wall Street working for Lehman Brothers in the mid-2000s, during the time the financial world was coming to recognize the value of marrying quantitative data to real-world experience. He recalled seeing an MIT computer scientist sitting on the trading floor with a 30-year trader, building a model together, creating something between them that was better than either could have created on their own.
Following Lehman’s collapse in 2008, Boehmig pivoted away from finance, enrolling in law school and teaching himself to code. He wound up an associate at renowned Silicon Valley tech firm Fenwick & West, working under the famous Ted Wang. Wang did something plenty of high-powered firm partners would find unthinkable: He allowed Boehmig to use a percentage of his billing time to work on improving the practice. Boehmig spent hours coding up productivity tools, trying to improve contract workflow and figure out ways to automate the day-to-day contracts that needed attention but weren’t valuable enough to merit a full attorney review.
Had Boehmig been required to simply bill his 2,200 hours and go home, Fenwick would have made marginally more money. Instead, by investing in developing its processes, Wang and Fenwick uncovered a massive opportunity to add value for their clients. The opportunity was so rich, in fact, Boehmig quit his day job to pursue it full time. My takeaway: breakthroughs don’t just happen. If a firm wants to distinguish itself from the pack, it has to spend the time and treasure in the short-term to search for and secure long-term gains.
Find A Way To Try
After leaving Fenwick, Boehmig had a vision for streamlining contract review. He soon had a co-founder, Ironclad CTO Cai GoGwilt, a computer scientist from MIT. With two techies and a good idea, I would have thought the next step would be to start coding for a few months and build a prototype. I would have been wrong.
Instead, Boehmig and GoGwilt started Ironclad as an entirely no-code system. Ironclad’s first customers paid a small fee and received an email address. The customer copied that email address any time they were working on a contract, and Ironclad provided bespoke advice and assistance in drafting and revising the contract. By first doing everything manually, Boehmig and GoGwilt were able to determine where they could make their biggest automation advances using real-world data, rather than intuition or educated guesses.
As lawyers, we’re used to preparing arduously, never letting a document escape our computer unless every sentence, clause, and comma is a polished gem. But there’s no better way to learn than to actually try something. If you want to test an idea, get it up on its feet as quickly as possible to see what does and doesn’t work (spoiler: usually almost none of it will work). Try, iterate, and try again.
Work Your Way Towards A Vision
Their hustle started to pay off. Boehmig and GoGwilt attracted seed funding from Y Combinator, bought a slew of IKEA furniture, and kept attracting customers. They iterated through new ideas quickly, validating what they could and scrapping what didn’t work. They had a series of useful tools and hacks but needed to understand what they should be building toward.
What they ultimately realized was that neither they, nor most of their customers, had an ambitious-enough vision. Customers had varied, niche needs. Some needed contracts to sign up Instagram influencers to push their products. Others needed NDAs for sales agreements. Franchises needed to streamline new franchisee onboarding.
Ironclad had tools to help with all of these, and customers were happy with the tools that helped them, but Boehmig and GoGwilt realized that having 50 separate tools wasn’t what they needed. If they wanted to grow, they needed to develop a single system capable of handling every one of these diverse tasks, no matter the complexity. Vision is important. Understand where you’re going, even if you don’t yet know how you’ll get there.
People Are Everything
Dropbox was when the fun started. Ironclad convinced the file-sharing giant to give them a pilot, which turned into a full-fledged relationship. Ironclad was soon in line for Series A funding, which it secured through Steve Laughlin at Accel. Boehmig connected with Laughlin on a shared philosophy: that a company’s people are a far bigger contributor to its success than the product it sells. Laughlin had been CEO of RelateIQ, a company known around Silicon Valley for the unusually strong team bonds within it. Accel’s funding helped the company grow on the balance sheets; Boehmig credits Laughlin’s shared focus on building the company’s culture for helping it mature internally.
The focus on personnel continued onward as the company grew. Series B went through Jess Lee of Sequoia Capital, one of the biggest and baddest names in VC funding. Series C went through Ali Rowghani at Y Combinator Continuity, bringing it back to the fund that gave Ironclad its initial seed. In each instance, Boehmig raved about the buy-in and passion of the company’s new partners. People come first. Plenty of lawyers can perform a given job. The only way to make magic is to have talent that care about each other and their shared goals.
Onward And Upward
With the holidays coming up, this will be my last column of the 2010s. I hope you’ve found something to take with you into the new decade, some resolution or glimmer of a good idea that will help you make your corner of the legal industry better. It’s been a long 10 years for the profession, and the next 10 promise to be just as full of challenges, opportunity, and surprise as the last.
James Goodnow
James Goodnow is an attorney, commentator, and Above the Law columnist. He is a graduate of Harvard Law School and is the managing partner of NLJ 250 firm Fennemore Craig. He is the co-author of Motivating Millennials, which hit number one on Amazon in the business management new release category. As a practitioner, he and his colleagues created a tech-based plaintiffs’ practice and business model. You can connect with James on Twitter (@JamesGoodnow) or by emailing him at James@JamesGoodnow.com.