During the first internet revolution of the late ‘90s, when John Orta was a young litigation associate, another junior associate at his firm inspired him to go to business school. They were working long hours together on various IP litigation matters while several of their contemporaries were striking it rich with the first-generation internet companies, a fact not lost on his fellow associate. “Law is hard and boring,” he said. “These business guys have it all figured out.”
So after thinking it over, Orta headed off to business school, but he never completely left law. Instead, he combined his legal and business experience, choosing positions where he can use both of his skill sets. He is currently general counsel at Metromile, the pioneering pay-per-mile insurance startup, where he oversees not only legal, but also the HR and recruiting teams.
Prior to Metromile, Orta also served in a similar capacity at OpenTable — the world’s leading online reservation provider — as SVP, general counsel, and head of people, making him responsible for all aspects of the company's legal, HR, recruiting, fraud, and risk teams. Orta is confident that neither legal nor business dominates his career. “My legal experience helps my business experience, and vice versa. They really do supplement each other,” he explains.
Orta credits his unconventional career path for his success at bridging the business and legal worlds, specifically the fact that he had time to focus solely on law and solely on business at different times. “I didn’t do a traditional JD/MBA approach. I had a chance to meaningfully practice law before I went to business school. Then when I graduated from business school, I had a series of business development roles,” he says. “As a result, I had great legal and business training.”
As he recognizes, he “was in a fortunate position to dedicate a chunk of time to law and then to dedicate a chunk of time to business, and understanding both sides makes it much easier to navigate the two worlds.” Over the course of Orta’s successful career as a business/law chameleon, he has gathered the following tips for anyone seeking to bridge the industry divide — both lawyers seeking to break into business, and business professionals seeking to break into law.
Be a business-savvy lawyer to get hired
Lawyers who want to break into the business world need to be actively interested in understanding a company’s business. As a business professional responsible for hiring, Orta emphasizes the importance of business skills for all professionals, especially in-house counsel.
When Orta hires attorneys for his team, business savvy is an absolute must. “I screen for attorneys who are curious and ask questions. As lawyers, we are almost always the only people in the company who read the fine print,” he explains. “So, we need to understand our business, why we do certain things, and what implications they may have for the future.” Orta explains that in any business, and especially for lawyers working in startups, good legal skills are table stakes.
“People on my team must do more, much more, than just redline the document,” he says. “People assume the lawyers will deal with warranty or indemnification provisions, but those are often the least important aspects of deal. The real value-add happens when in-house counsel understand the business objectives so that they can accurately describe — and often question — the structure of the arrangement.”
Numbers are important
Remember that joke where a graduate goes to law school because they’re bad at math? Orta does not think it is funny. He strongly believes that any lawyer hoping to transition into the business world needs to have some skill with numbers. “It is hard to build a company on a purely qualitative value proposition,” he explains. “That is a sure road to a business failure.”
This is where business school can be helpful for lawyers who, like Orta, are dedicated to transitioning into business. Lawyers who are “bad at math” can learn these skills in business school. Law students who are already considering a business-related career can even take classes on essential math skills, such as financial statement analysis, while earning their JD.
However you attain it, a grasp on numbers is a must, according to Orta. “Numbers move markets. Numbers build business. Numbers explain partnerships. If you can’t follow the money, your value at the table is highly limited if it exists at all,” he says. “At the end of the day, lower costs, higher revenue, more customers, and other similar quantifying metrics dramatically increase the odds of success.” A business with no numbers is like a bird without wings — it just won’t fly.
Listen before asking questions
Orta explains that the business world is much more of a team sport than many legal endeavors. You can’t be a good team player unless you listen first, and then show a genuine interest in the ideas of others by asking relevant and meaningful questions,” says Orta.
According to Orta, it is not a coincidence that the most successful business people ask many great questions. “There is an art in asking a question,” Orta explains. “You must listen with intent toward identifying and truly understanding the issues, the impact of those issues on the company, clients, and employees, and the importance of a timely solution.”
To succeed in a business role as a lawyer, Orta also recommends checking your ego at the door. You will likely work with colleagues who have less education, though possibly more experience, than you do. You need to be open minded to all ideas. “For example, one more than one occasion I’ve discovered what provisions in our contracts might be confusing by listening to feedback from the sales and customer support teams. Easy fixes like that make everyone’s life easier.”
Create relationships that transcend jobs
Networking is important for anyone trying to transition between industries. Orta also emphasizes the importance of building long-lasting relationships with business professionals. “At every job since business school, I’ve worked with someone who knew my work,” he explains. “For example, I found my current opportunity at Metromile through the Head of Product who I worked with at OpenTable.”
Similarly, Orta says, “I found my opportunity at OpenTable through the CFO, with whom I worked at E-Loan.” Orta emphasizes that the business world is small, and the startup world is even smaller. “Ultimately people, and business people specifically, like to work with people with whom they’ve worked well in the past.” It is wise to build deep and wide relationships at work if you are at all interested in transitioning to a business role.
Roll up your sleeves
As a startup veteran, Orta highly recommends that lawyers try the startup route. “Startups are a perfect place to break into a business role, though keep in mind it is not as easy and as glamourous as it sounds,” he says. “You should be prepared to do whatever it takes because at a startup everything is a team effort.”
Although startup life can be difficult, it’s a true trial-by-fire experience that can teach you more than a traditional business school class. If you manage to break into the startup world, be prepared to work hard in order to reap the benefits. “It is not unusual for startup lawyers to do much, much more than a traditional legal job in a law firm or in-house,” Orta explains. “If something needs to get done, just roll up your sleeves, show your commitment and value, and then learn a lot of business skills in the process. Even manning the front desk — which is something I do regularly — will teach you a lot.”
On the fence about making a career transition? You might be better suited for it than you think. Orta notes that we are increasingly seeing lawyers transcend the business, law, and technology boundaries. For him, Belinda Johnson, chief business affairs and legal officer at Airbnb, and Kathleen Philips, chief financial officer and former general counsel at Zillow, among numerous others, exemplify this trend.
Orta believes this is because many lawyers have the skills to be business professionals, and vice versa. “Some lawyers are also sharp business people. Some lawyers are also very good managers and can inspire others,” he says. “Just because someone has a JD or is a member of the bar association doesn’t mean they’ve checked their business sense at the door.” In fact, Orta strongly believes in evaluating lawyers on multiple dimensions, just like we do with all other business professionals.
For example, Orta is a skilled attorney, but also has HR skills. “I love being responsible for HR. It gives me immense pleasure to figure out how to discover, hire, and retain talent. And talent is a big part of success in Silicon Valley, where daily competition for talent is fierce,” he says.
Becoming a business/law chameleon has given Orta a more satisfying, multi-dimensional career, where he can pursue this interest. Likewise, making an industry transition could be the right choice for many other lawyers and business professionals. Ready for a change? Orta’s tips can guide you through a seamless transition into the intersection of law and business.
