Root Insurance Company gave me my first general counsel position, apart from an opportunity I had for a year back in the dotcom days for a startup called eGovNet. There, I also marketed, I did procurement work – but it was a small enough organization that ‘general counsel’ was really a plank of what I did.
Before that, I’ve spent probably two thirds of my professional career in and around government. I’ve worked as chief of staff to the Governor of Ohio, handling regulatory agencies, and then outside of government, either with my own consulting firm or as a law firm partner. Throughout that time, I’ve had opportunities to work either directly with or for the insurance industry – Root is the third insurance company that I’ve worked for. I did the government affairs work for State Auto Insurance all over the US, and I was in senior management on the operational side of the business at managed healthcare plan CareSource.
Now I’m at Root Insurance, I am the first and only general counsel (the team is just me) for a rapidly growing personal auto insurance company, learning to wear many hats and to manage everything that comes at me every day.
The business of insurance is highly regulated, and the fact that I have been a regulator in the past, have worked with regulators for decades, and have an appreciation of the big challenges and opportunities of a regulated industry is probably the greatest strength that I brought to this role.
The learning curve for me has been primarily on the corporate transactional side, but fortunately the company already had relationships with some terrific outside corporate counsel, who continue to assist. Getting up to speed and understanding the twists and turns and history of the company, and being able to put that into context to give really good advice has also been a learning curve.
The other part of the learning curve is around privacy and security. It’s not that I was unaware of restrictions in the law around privacy and security – having worked for insurance companies, and certainly working for a managed healthcare plan where health information is involved, I’ve had to be aware of the risk – but that’s another place where I’m getting up to speed.
The primary reason for me coming back to the law was the excitement of working for a startup that really is disrupting the auto insurance business. To be with Root almost from the ground up at this stage of my career seemed to be a very exciting chance to take.
We are a mobile-only personal auto insurance company. All of the policies that we sell are through a mobile device app that our customers download, and we use telematics data gathered from the customer’s smartphone in order to assess their driving. Along with other insurance rating factors, we then decide whether to offer them a quote and to help us price that quote.
I think it’s fair to say that we are, by our very nature, innovative, disruptive and focused on growing our footprint. We are always investing and innovating in our core technology and, as a general counsel in a regulated startup, I interact very regularly with our product team as they contemplate options for improving our app. They often have questions for me about how that functionality will work, and how we will describe that functionality back to our customers.
There’s an opportunity at a company like Root to work with some very bright software engineers, marketers, data scientists – folks who have significant IQs, but they haven’t been in the workforce that long because they’re young. I’m very proud of the work that they do, and I see every day I work with them as an opportunity to not only answer their legal questions, but also to use my experience to help them think about how to frame those questions, and to always make certain that we are looking at any problem or opportunity through the lens of our customer. If I had any moment of pride in my first four months, it would be that I have built the trust of this team, many of whom had never worked for a company that had a general counsel or any in-house legal staff at all.
Certainly, when I’m able to see what they’re doing with AI and large amounts of data, they are providing me an opportunity to learn a lot. They see unlimited business opportunities with the technology, and when they come to me with an idea, they are appreciative that I am going to hold the line with compliance, but that when there are gray areas, I will always do my best to make sure we err on the side of saying yes to innovation and opportunity. Sometimes that means taking some risk in gray areas of the law – for many people, their experience with auto insurance is via a relationship with an agent. In a business model where the agent is not present and we are doing our best to completely serve our customers through an app, many of the insurance laws have not yet caught up.
Because Root Insurance Company is so disruptive, I will look to use what I’ve done in the past with government affairs work to shape public policy going forward. It’s my agenda to work with regulators and to look for opportunities to make sure that the laws contemplate and permit our business model, ultimately for the benefit of the consumer.
GC: Now less than a year out from the United Kingdom’s scheduled withdrawal from the European Union, how would you characterise the current state of negotiations between the UK and the EU? 
