Category: Interviews

I have always been attracted to public service. A number of my colleagues from my time at Gibson Dunn had gone on to serve as solicitors general in state attorneys general’s offices. Those offices provide unparalleled opportunities, such as the chance to argue appeals and challenge areas in which the federal government has exceeded its powers and placed onerous regulatory requirements on the state. So I was very grateful to have been offered the opportunity to work in the West Virginia solicitor general’s office.

In 2017, I became the general counsel of the FCC. I’m primarily responsible for two components – reviewing Commission rules and orders to ensure they are legally sustainable, and defending those actions in court. I also oversee units that deal with fraud and bankruptcy issues, as well as various internal issues like employment matters. In West Virginia, I supervised four or five attorneys at any given time. Now, I oversee a team of more than 70 lawyers, so I’ve had to focus a lot more on learning how best to allocate my time, how best to delegate, and who are the best people to delegate various issues to.

I came into this position with very much a generalist understanding of administrative law and appellate law. And while I had done some communications work in the past, I definitely rely on staff to brief me on particular areas that require a lot of technical or substantive expertise. But one benefit of bringing a generalist perspective is that I’m in a good place to understand what sorts of questions and issues a judge might have and how they will approach reviewing a particular Commission action, and to ensure that what we’re doing is likely to be upheld in court.

I think the first few weeks in the role were probably the most challenging – you really inherit a whole world when you come into a federal agency, and so the early days are occupied with learning new names, learning people’s responsibilities, and learning the various practices and processes at the agency. Once you’ve had some time to reflect on that, then you can start to think constructively about what’s working, what’s not working, what you’d like to change and what you’d like to improve.

Along with one of the new deputies that came in with me, I spent a lot of our early weeks scheduling meetings, both with different team leaders from the office of the general counsel, as well as with our stakeholders in the agency. That meant they could put a face to a name and we could show that we could learn about what they were doing and also how we could improve the relationships between the office of the general counsel and other offices within the agency. We have tried to create an open door policy so that folks who have pressing issues can come to us directly. That’s the way in which we tried to immerse and integrate ourselves early on.

Oftentimes, the perception of a general counsel, whether it be in a federal agency or in the private sector, is of someone who has the unfortunate responsibility to say no a lot of the time, and that person takes on a reputation for impeding progress within an organization. I think that a GC certainly needs to be aware of the legal prohibitions, and there may be times when they need to say no, but that person should also think of themselves as a facilitator, to help further the agency’s mission consistent with the law. In the gray areas, the general counsel needs to be clear in articulating what the various legal risks are, but to also help the organization achieve its objectives.

Unlike in the private sector, we don’t have the option of using outside counsel to represent us for particularly challenging or time-intensive matters. That’s part of the challenge, but it’s also part of what makes the job exciting. At the FCC, we have our own in-house litigation division, so that’s different from some agencies, who rely exclusively on the Department of Justice to handle the cases that end up winding their way to court. It allows us to be more holistic in how we approach legal problems, evaluating at the outset whether the rules or the orders that we’re adopting are easily sustainable – with one eye towards what sort of arguments we can make if they are challenged in court.

Another consideration is that attorneys in private practice divide their time amongst multiple clients, but when you work for the government, your client is ultimately the people. This means there’s much more focus on how the positions you’re taking will serve the public interest as a whole – not only in the case in front of you, but also long after you’ve left office.

One benefit of being in a management position working for the state is that it allowed me to be a lot more entrepreneurial. The attorney general was very receptive to attorneys coming up with ideas of how best to further the state’s interest, even if that meant initiating a law suit in federal court to challenge federal rules as unlawful. Because we had a lot of authority and ability to think of creative solutions, there was also a lot of trying to stay on top of legal and political developments in the news and trying to ascertain how we could best further the agenda of helping the people of the state when the federal government passed a rule that could adversely affect their interests.

Another thing a general counsel in federal government can do is focus on institutional issues that will affect the agency – not only in your time – but also in the future. There are some perennial issues that agencies encounter, like: how do we fund our programs and activities, how do we manage documents and data collection preservation? While these are not issues that take up a majority of my time, they are mission critical, so they are opportunities to think through how to set processes and procedures in place that will be consistent with both our legal obligations but also introduce efficiencies into the organization so that future people who come into my position will benefit.

Looking ahead, the increasing complexity of the modern administrative state will mean that general counsel are going to need to be much more interdisciplinary and also conscious of what their counterparts are doing in other agencies. There are a lot of areas where agencies share jurisdiction, where jurisdictions overlap, where consultation is required by law, or where review is necessary before action can be taken. So it’s increasingly important for general counsel to know what those requirements are, who to call at other agencies to get things done, and who the different stakeholders in the process are.

I also think that keeping on top of technological developments is going to be important. The tools that lawyers are using to do their work are constantly evolving, and the role that social media is playing in government messaging is evolving. And in the private sector, with respect to a lot of the entities we regulate, oftentimes the law may not evolve quickly enough to catch up with technological change. These factors are going to present challenges for lawyers to exercise good judgement in determining how existing laws apply to new technological developments and unforeseen situations. The answer in a lot of these cases will be for the federal government to get out of the way of competition and technological developments that are occurring.

There are two pieces of advice that I would like to give other attorneys.

The first is to be flexible in your career path and open to taking risks when a new opportunity comes your way that excites you. I would never have believed it if you had told me a few years ago that I would be deputy solicitor general of West Virginia, and then general counsel of the FCC, but those opportunities have been both a really enjoyable and rewarding experience, and I would encourage other lawyers to do the same.

The second is that it’s really important to cultivate a reputation for integrity and excellence among your peers starting in law school, because those are the people who one day are going to be in a position to speak to your character and your qualifications if the right opportunity comes along.

I graduated law school during the dotcom boom and quickly determined that I wanted to be part of that excitement. But by the time I got to Silicon Valley, it was 2001 and the bubble was crashing. I landed on my feet in 2005 at DLA Piper, where I spent almost half of my career, culminating in a partnership in the corporate group. While at DLA, my practice focused primarily on representing public companies in SEC reporting and corporate governance matters, and M&A and capital markets transactions.

Early on, I had a sense of wanting to go in-house: I viewed an in-house role as being more than a transactional lawyer; you delved deeper into the business and the position required you to become more practical and solutions-oriented, more of a decision-maker, in my mind. I secured my first in-house position at Caesars Entertainment, which was the perfect transition for me. Caesars’ global legal department was comprised of many lawyers from large law firms and had a general counsel with a strong presence and sense of team and practicality. While at Caesars, I practiced primarily in areas in which I was most comfortable, including SEC reporting, corporate governance, and capital markets (equity and debt) and M&A transactions. I worked closely with the finance and treasury departments, advising them on legal issues relating to Caesars’ more than $20bn of debt, and advised Caesars Interactive Entertainment on various corporate matters and acquisitions. At the same time, I was able to learn how in-house practice differs from that of a law firm.

Next, I was presented with the opportunity to become deputy general counsel at Everi Holdings. Going from a large company to a smaller one presented new learning experiences for me. I became much more intimately involved with the board and senior management and had to deal with a much broader set of legal and business issues. I was also directly responsible for managing more people, including lawyers and non-lawyers. In addition to advising the board and senior management directly on issues with which I was intimately familiar, such as SEC reporting, corporate governance, and debt-related legal issues, I also played a large role in managing litigation and advising the company on issues relating to human resources, intellectual property, and customer and vendor contracts. My role at Everi also allowed me to work with senior management to implement and improve various business processes throughout the company.

In early 2016, just as I was getting married, I received a call from DLA, offering me the opportunity to return to the Washington DC area as a partner in their corporate practice. I accepted the partnership and the chance to return to my home state of Maryland. While my return to DLA presented me with a plethora of challenging and complex legal issues in a short period of time (including representing a private-equity backed company in a $400m raise, immediately followed by a $500m IPO and a $3bn refinancing of the company’s debt), my law firm experience was exactly as I recalled. With my first baby on the way, maintaining the ever-elusive work-life balance was even more difficult. On top of that, I yearned to re-embrace the different challenges provided by an in-house role. The opportunity at Live Ventures allowed my family to return to Las Vegas and was exactly what I was seeking – a general counsel role with a small-but-growing public company.

Live Ventures is a public holding company that operates multiple businesses in different industries, including two retailers (Vintage Stock and ApplianceSmart) and a carpet manufacturer (Marquis Industries). Understanding a company’s business is crucial to any in-house role, and Live has three of them. Our subsidiaries operate independently and often with wide latitude, so the biggest challenge is integrating myself with senior management, both here at corporate and with our operating companies. I need to ensure that the business people know that I’m here to help and advise in any way I can, including navigating the challenges of being part of a growing public company.

For those considering going in-house, I suggest that you round out your legal skillset. At a firm like DLA, you’re focused on mergers and acquisitions or capital markets transactions, for example, and if you have an issue regarding a commercial lease, you reach out to a real estate colleague. At Live, I’ve worked on more commercial real estate leases in the past few months than I had in my entire career. So if you’re at a large law firm, it’s really about trying to find that odd project, embrace it, and try and use it to your advantage to learn something new. I know it’s challenging with the way larger firms are structured, but I think that broader skillsets translate better for in-house positions.

The other challenge, particularly for the general counsel role, is learning how to manage people – both up and down the organization chart. It’s not something they teach you in law school or at a law firm, but soft skills play a much larger role in-house than they do as outside counsel. Oftentimes, for me, applying appropriate soft skills presents the most challenging part of the role. You can’t talk to HR the same way you talk to opposing counsel, or the same way you talk to your own outside counsel, or the same way you speak to your CEO and CFO.

Also, ivory-tower-thinking doesn’t have a role in-house. It’s almost as if you’re apologizing to a business person, and saying, ‘Look, I’m sorry we’re talking about this in this manner but unfortunately we are talking about a theoretical legal issue here, and this is something that may come up down the road depending on what direction the company takes.’

Law school teaches you how to analyze issues, research, and write memos, but there’s very little practical training. Law firms provide some of that practical training – teaching you how to draft documents and negotiate, for example. In-house practice is very different from firm practice – you must be practical and find solutions; you are an adviser of risk and counselor to the business team. A lot of outside counsel claim they are practical and business-oriented, but the reality is the business team does not want to be negotiating every word and obscure provision where there is little risk. Finally, you must be able to communicate in a crisp and precise manner, using language the business team understands. Long emails and memos are not going to make you a successful in-house lawyer.

At Live Ventures, we don’t have a panel. Selection of outside counsel is relationship-driven: relationships developed by senior management, the board and myself. I learned a long time ago that you hire the lawyer, not the firm. A firm may have a great reputation, but if the lawyer’s not practical and helpful and is unable to communicate in a concise manner, then the firm’s reputation doesn’t matter. It always amazes me that lawyers think they are building relationships by billing their clients .1, .1, .1 every time they touch a matter. I see those bills and cringe, because that tells me that the outside counsel does not view us as a collaborative partner – we are simply a revenue source. Alternative fee arrangements are something we now look at on every new project – and we expect our legal counsel to do the same.

I believe companies that can continue to bring work in-house will do so (although some companies have taken steps in the opposite direction). I think the larger, elite law firms are appropriate for larger, more complex companies, and bet-the-company transactions regardless of a company’s size. But those of us working in smaller, budget-conscious companies who come from a sophisticated outside counsel practice can leverage our own expertise in-house and our own relationships. Elite firms serve a purpose, but I think there are plenty of lawyers who have previously practiced at those firms, yet bring the same capabilities and quality advice at a much better rate; these are the lawyers we seek out.

I think there are a lot of lawyers who have a vision of their career when they first start out, but I was not one of them. I didn’t have a plan to become a general counsel, for example. I simply had the good fortune of meeting the right people at the right time and being open to new challenges. My career path has been about the people that I’ve met who have been my advocates and promoters along the way.

I started my career clerking for a judge who is now the US Senate Majority Whip, John Cornyn. He was someone who really valued his staff’s views and insights, and I wanted to be a courtroom lawyer in front of judges who respected me like the judge I worked for did.

But as I said, my path has been about the people I’ve met along the way. It was for its people that I chose to go to Southwest Airlines to be head of litigation. Southwest is an airline that was founded by a lawyer (Herb Kelleher) who made it his mission to ‘democratize the skies’ in the US – to make it possible for everybody to be able to fly. I was fortunate to have been a part of that for over nine years.

The opportunity at Spirit AeroSystems arose, and again it was due to a prior relationship – somebody I worked for in the past recommended me for the job. Spirit was an opportunity to go from an airline to an air structures manufacturer, getting to be a part of a global business with operations in the UK, France and Malaysia, as well as multiple places in the US.

To come to the general counsel role was a big leap for me, and I was fortunate that in the past I had had a very diverse litigation practice that included, for example, corporate governance issues. Also, in private practice, I had worked as part of the defence team for CEO Kenneth Lay in the Enron litigation in the US, which was, of course, a huge changer of basic corporate governance tenets. At Southwest Airlines, I also got to do a lot of regulatory oversight, corporate investigations and the integration of another airline. All of those things were very helpful for prepping me for being GC, at least in terms of the legal role.

But the biggest leap was the business, and going from an airline, which is essentially customer service, to aerospace and defence manufacturing. That was an enormous learning curve, and remains so. I read everything I could get my hands on before I got here about the industry. There were people within Spirit who I reached out to, to learn what we do and how we do it – for example, taking tours of our manufacturing facilities, walking through the plant floor to see what we make and talking to the people who make these aircraft structures, and also spending time digging in with our corporate controller to learn the very different financial and accounting aspects of a manufacturing business versus an airline.

At the time, the best advice I could have given myself is that I don’t have to learn everything today. In the first few months I was here, I felt that I needed to know everything right away and, in all of the work that I did trying to learn as much as I could, I neglected myself. Have a plan for all the learning that you need to do, but make sure you are making time to sleep. Taking the job meant moving my whole family to a new city. I have children, and I did not sufficiently take into account what that transition would be like for us on a personal level. So I think you have to learn that you don’t have to know it all on the first day. Have your plan and make sure you take care of yourself in the process.

The things that I find most rewarding really centre around people that I’ve had the privilege to lead who have gone on to do tremendous things in their careers or try new challenges. I’ve been most proud of the teams that I’ve put together and the smart people on those teams. On the flip side of that, the most challenging moments have been ‘people moments’ – learning how to adapt and work with people who don’t operate with the same core principles and values as I do. It’s really tough to stand on an island alone, but sometimes you have to do it. At Spirit, we’ve just begun the journey of shifting our culture and our values, so those most challenging moments are learning that not everybody yet has bought into those core values and principles, and having to learn how to influence people to get on board.

Fortunately, the single most valuable thing that contributed to my view of leadership was the leadership program that I went through at Southwest Airlines. I was actually the first lawyer to go through it, and it taught me the importance of having a core set of principles and values and instilling them in people across your business, so that everybody is operating from the same set of guidelines in making their business decisions. I think that’s no different from understanding your company’s risk appetite or strategy – if you don’t know what those things are, you don’t know the framework for the decisions that you need to make.

Since I’ve been here, I have expanded my leadership to our compliance team, I have taken on our global contracts team, and I will be taking on the information security team – the chief information security officer we’ve just hired will report to me. As you see the general counsel role expanding to really influence business strategy, I think it will also expand to have more leadership of some of these non-legal areas because of the interconnectedness of them. Most businesses will benefit from a general counsel who has some oversight and an intimate involvement with all those other foundational elements of the business.

There are other things throughout my career that helped prepare me for my job at Spirit. I had stepped into my role at Southwest Airlines at a time when e-discovery was just coming into effect, and so I was able to be pretty innovative in the leadership there in getting us to a sophisticated state in our litigation practice. Coming to Spirit, I would say I’m bringing innovation, but it’s not new things; all of the things that I did at Southwest I’m bringing here now. Spirit just hadn’t had the opportunity or the need to get current in the same way.

For example, I have started doing something that’s pretty common in our industry, but wasn’t common at Spirit, which is unbundling the legal services. We’re not hiring law firms for every aspect of a litigation matter or due diligence, for instance, because there are non-traditional legal service providers that you can couple with a law firm, which are a lot more cost-effective. We’re bringing in things like technology-assisted review and artificial intelligence, which started in e-discovery and now we’re expanding over into revamping our contracts management. If you can use tools like AI to help you gather more information about your state of compliance and contracts management, then you’re going to equip your lawyers to deliver much more efficient and practical legal advice.

I think this represents a broader trend. I’m surprised we still have as many very large law firms as we have. At Spirit, we do hire large multinational law firms, but I am personally a fan of smaller practices that I think deliver better value for the client, depending on the matter. There are times when you need a firm with a global presence, but I continue to believe that we’re going to see more boutique-style law firms that really understand their clients’ need for practical advice that furthers their business goal. And I really think we’re going to see more service providers in this area where we’ve unbundled various things. There are companies that are not law firms, but which have lawyers you can use on a project basis with your law firm partners on matters – sort of an ‘à la carte’ menu where you can piece together what you need. More law firms will, I hope, start to see the benefit of partnering with those non-traditional service providers.

I joined Mastercard in 2000 and initially spent seven years in our law department. Then, I spent seven years or so in a series of business roles – I was chief of staff to our chief operating officer doing strategic work, financial planning and sales planning. It was a senior staff role, which is often how lawyers can move effectively from the legal function to the business side. From there, I went to run our North America markets, and for the first time I had a P&L and actual account responsibility, which is a bracing challenge for anybody, but particularly somebody coming from a legal background. Because I was deep in that market and understood some of our challenges, I was asked to take on the role of chief product officer, which tested me in a whole new way.

One of the strengths of Mastercard’s culture is that it seeks to move people around and give them diverse responsibilities, and I really was the beneficiary of that. I joke that I was qualified for exactly none of the jobs I had except for the first one! And in a strange way, all that moving around made me better qualified to be the general counsel.

So, coming back into a legal role did not feel like a significant leap, because I had both wide-ranging previous experience in legal and risk management, as well as having spent seven years with a lot of access to the board of directors and helping to drive the company’s business strategy. In the product organization I had been given the opportunity to manage a relatively large team, and so the opportunity to come back into the law organization and drive a focused transformation agenda was very exciting.

It goes without saying that in the GC role you need to really make sure you put on your risk management hat. That isn’t to say that I didn’t feel accountable for risk management in my business roles, but there’s a special accountability here, and trying to be intentional about flexing that muscle, consulting widely with people and using my business experience to advise on legal risk was a key part of my initial agenda as GC. These were all an important part of coming back in to the law department.

One of the things that I’ve found is that as in-house lawyers, we need to always be selling, meaning that we can’t take for granted that our colleagues understand or appreciate the critical work we do. Business people tend to communicate simply and crisply, whereas lawyers can, at times, go on forever. Just being able to talk to my own legal teams about things like simplicity of communication, managing to metrics and leaning into the company’s strategy has been a pleasure to bring to the department. You need to tell your colleagues it’s a priority: you need to get their buy-in and acknowledgement, so when you are successful it doesn’t look like a random walk, it looks like very important strategic work, which it in fact is. That is so foundational, but it so often doesn’t happen. In-house lawyers need to be selling their services and their value.

We’ve really worked hard on a metrics-based scorecard of things we wanted to achieve – some strategic and some tactical. It is such a natural instinct for business leaders – every business leader manages to a P&L or some sort of balanced scorecard of hard numeric metrics. For lawyers, on the other hand, it is really hard, and a lot resist it. But at the end of the day, if you push hard enough, I think every legal function can find a metrics-based scorecard to measure themselves. That’s really powerful because it speaks the language of business, and it’s a great way of demonstrating value to your board, your CEO and others.

We are shifting a significant portion of our work from lawyers to a shared service function with our finance team. Now, at Mastercard, if you do a non-disclosure agreement with us, it’s done by staff in the shared service function, and that shared service function has all sorts of automation and it tracks – in a very rich way – timelines and response rates and so on. It has allowed us to use knowledge in entirely different ways. We are revamping all of our customer-onboarding systems to make them much more digital- and user-friendly, we’re bringing mobile-based solutions to all compliance requirements, and we’re really trying to show up as a mobile first, digital savvy organization. If Mastercard is going to grow 10, 15%, I want to be able to support that growth, but at the same time grow our expenses only by a very small fraction of that 10, 15%.

In a legal department, it’s very easy to revert to: I’m a service organization and I will do what the business brings me. That’s reactive. We have a critical role in driving company strategy: understanding that strategy, figuring out the components of it, influencing it, and finding ways for legal and policy and other things to not only enable the strategy, but to advance it.

‘I’ll give you an example. We’re increasingly seeing that good privacy policies are a competitive differentiator. In light of GDPR, my legal team has created a groundbreaking venture called Trūata – which is a method of anonymising data so that it can be used appropriately while protecting consumer privacy, consistent with the new regulations. It came about because lawyers went to the business and said, ‘Look, we have to do this but, by the way, we can get a competitive advantage if we do it well. Let’s drive this thing.’ This is an example of how, if you’re just an order-taker, marking up contracts, then you’re not doing all that you can do.

I think that there is growing demand for the GC to be a trusted adviser to boards. The GC must be the keeper and the guardian of the company’s ethics and its culture, including in areas well beyond its traditional remit. Being part of those conversations, always doing the right thing and absolutely insisting on good ethics and compliance are so important. We’ve seen how incredibly destructive some of these divisive cultural issues can be if they’re not managed the right way.

It’s really hard to overestimate how much time and effort goes into board and governance issues. That continues to surprise me, even four years into the role. Getting the narratives right to the board, not just on my own things, but helping the company do that well overall so that we have effective meetings and get to good conversations – boy, it’s time consuming. You’ve got to make sure you’re resourcing for it, because it can take over your role.

In my job, I could do nothing but government outreach and it still would be really hard to cover everything I need to. This aspect of the job is that important and demanding. Given the choppy geopolitical waters, it has never been more important to make sure you’re not just stuck in the office, but you’re out there talking to governments and stakeholders, you’re advocating and being an ambassador for the firm. The reality is that there are only a few people in an organization who can really get top engagement, and demands on GCs are increasingly high as a result.

In terms of the role of the GC going forward, I do think new skills may be needed on the external ambassadorship side. If you can give a good speech in a TED Talks style in front of 200 economists in a leading country and come off as pretty compelling, you’re adding value to your firm. The best skill you can ever get anywhere in life is public speaking. It’s not rocket science; being comfortable in a public role can be learned.

The world is going through enormous change, not just in technology, but also geopolitics. For multinational firms, from a regulatory and public policy standpoint, the future is going to be harder. Norms that have been around since the Second World War are really changing: Alliances are fracturing, we’re seeing trade issues; we’re seeing nationalism on the rise; prevalent data privacy issues. Societies are looking for private companies to take positions on social issues that are enormously complicated. So the job is harder than it’s been because of those things and I think we need new models and approaches to addressing them. Trying to do it alone isn’t likely to be successful. Being a GC, not in a steady state, or even in a growth state with known paradigms, but in a state where all the paradigms are being thrown up is difficult, and we need to do more work on our tools.

I think that coming from an in-house role to the GC position is an easier transition than going directly from being a partner in a law firm, because the role is so different. Being the outside lawyer, you don’t have the perspective of the consigliere. Although folks can obviously be successful that way, I think that’s a bigger jump.

I would have loved to work in more industry sectors! But I think the unique thing about entertainment is that once you’ve started down that road, if you try to interview outside of the industry, there’s a lot of scepticism. People wonder why – it’s a desirable, sexy industry and people are more often trying to break into it rather than break out of it.

I have loved the job since I’ve been here because of the variety that it presents. One day I’m working on an FCC filing, the next day it’s a shareholder litigation, the next day it’s a big contract with our biggest licensing partner. I also like the opportunity to really feel like you are making an impact at the highest levels on the direction of the company – that’s something I hadn’t experienced before I became general counsel.

Just as I was starting the job, Starz went through something that was pretty unprecedented for the company – it was dropped from one of its distributors. Going through that entailed a lot of regulatory and political work, as well as transactional negotiations that was a huge challenge for me and for the rest of the company. Coming out of it with a deal was something that I’m proud we were able to achieve.

The general counsel position is in essence a generalist role. You’re not just the transactional lawyer, you’re also looking at litigation, regulatory issues, political issues, all of those things, and I don’t know that it’s very easy to get that experience prior to taking on the role. I was primarily a transactional lawyer – IP and entertainment – so I had done the corporate M&A stuff, the securities stuff, and also done IP and entertainment licensing and distribution, but I hadn’t done litigation. I had been involved, but I wasn’t the one leading litigation. I hadn’t done production work to the extent that I’m now responsible for. The best preparation you can do is to get involved in a lot of different things and try to get the broadest experience as you can. Even as a transactional lawyer, I would support litigation, which was useful experience.

When I was at Sony, I had been doing a certain type of entertainment work; I was good at it and it was my area of expertise. But after five plus years of doing that, I obviously wasn’t learning as much – it was like the back of my hand. I was looking around at other opportunities within the company and somebody advised me to consider another area in order to get experience I didn’t have. My response was: ‘Yeah, I’d be willing to try that, but I wouldn’t want to give up what I have now.’ I wanted to take on new things, but I didn’t want to let go of what I had.

The person wisely said: ‘You already know that stuff, it’s on your résumé, nobody can take that away from you. Everybody will know that you are an expert in that stuff after having done it for five or six years, so it’s ok for you to let that go in order to take on other responsibilities – and it will be better for your career growth.’ He really encouraged me to let go and make room for new things, and I thought that was really great advice. As soon as you’ve mastered something, it’s time to move on and get some other experience.

I’ve always told my teams, whether it was at Sony Pictures, Lionsgate or at Starz, that we need to advise the business not just from a legal standpoint, but from a strategic standpoint. When you think about a contract, the parts that are purely legal are all pretty boilerplate and a very small part. Our role is to bring up all of the concerning business points that might come up in a contract: does it really make sense for this agreement to be non-exclusive, does that fit with our strategy? Does it make sense for this to be a long-term deal? Maybe we want more flexibility to do this other thing next year? It’s really advising on the business strategy and what you see coming up in the future to help them achieve their business goals. I feel like I’ve been doing that since I started being a business lawyer and this is just a little bit more official now that I am general counsel.

I’d like to think that there was a move towards having more women in the GC role. I don’t know if I would say that mentoring and nurturing of diverse attorneys is increasing in the entertainment industry, but the Weinstein scandal may bring on some change. Maybe it will make women feel a little bit more emboldened to speak out about the need for diversity in the workplace – they can now point to that, so it doesn’t have to be so personal. Companies are letting go of people for all sorts of reasons related to the Weinstein issue, and it’s exciting to see that change is happening. I don’t know if it’s going to be sustainable, but there’s definitely more awareness and sensitivity than there ever has been before.

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.

Working at a dotcom was the first time I really got inside a business and became part of the leadership team – and obviously the dotcom era was a moment in time that was incredibly instructive for people to understand what a bubble looks like.

Some things were very different to my role now at Nielsen, and some things were very similar. It was more of a start-up environment, the legal department was much smaller, and it was largely a US-driven company. Nielsen is a much larger department, and it’s a much larger, global company. That said, the fundamentals are pretty consistent across the board. You’re trying to help grow the company, do so in an ethical, compliant way, and you’re continuing to try and be creative as you address issues.

In legal services, I think there are certain consistencies and evolutions. Technology is very different now to when I was in-house last time, and I think technology will likely be very different five, ten, 15 years from now.

If you’re in a small organization, the opportunity to have a broader role is greater. As an organization grows, things tend to get a little more siloed and remits tend to narrow a bit. But on the other hand, CEOs for the last decade or so have really begun to see that general counsel with certain skillsets and temperaments can add value in areas beyond the traditional scope of work assigned to a GC or CLO.

One thing I’m seeing in other companies – and have experienced myself here at Nielsen – is that the remit of the general counsel tends to be expanding. For instance, I joined Nielsen as the CLO and had responsibility for the legal department. Since then, my remit has expanded to include security, corporate social responsibility, government relations and public policy, as well as enterprise risk management. The job is becoming broader (which I happen to like) and I think boards and CEOs are recognizing that a GC may bring a host of skills that extend beyond simply running a legal department.

I don’t know exactly what I expected when I became general counsel at Nielsen, but it is different. In a law firm, you’ve got a large portfolio of clients, but once you go inside, you have one client. It can be a large, complicated client, which Nielsen is – with around 45,000 people spread across the globe in more than 100 countries, and multiple businesses in various legal and regulatory regimes.

You get much more involved in the business of the company in a leadership role. The kinds of things that cross your desk are incredibly diverse, and as diverse as private practice was, this is much more so.

Another key difference is that as outside counsel you try really hard to develop close relationships with your clients, but there’s a certain distance that you’re never going to be able to overcome, regardless of how good you are. Ultimately, you give advice and then the client takes that advice as an input and makes a business decision. When you’re inside, you give that same advice, but you live with that decision. You can’t walk away, so you have to own it from a perspective that’s not simply about what the law is, but what the company’s risk analysis is, what the business’s objectives are, and a whole host of other factors that you need to synthesize.

The hierarchy of a corporate structure is much more defined than the hierarchy of a partnership. That colors a lot of how I think about my own behaviors. For instance, when I speak to people, I know that often they are hearing the chief legal officer, they’re not necessarily just hearing a colleague. So trying to think not only about the matter that I’m discussing with them, but also their frame of reference, is a little different than in the past.

In a law firm, they have partners and associates. I initially analogized my position at Nielsen as me being a partner and the rest of the department being associates. I quickly learned that this was a poor analogy! A better analogy is more along the lines of being a managing partner in a law firm and that there are a lot of other partners, as well as associates. At Nielsen we have really smart, accomplished, independent lawyers who have great judgement and can run with matters often with little-to-no input from me – they know how to reach out to me, and I view my role as largely to help them do their jobs and clear obstacles and work through issues when they want a sounding board. That’s a very different dynamic than the frame of mind I came in with.

I read everything when I took the job at Nielsen – I read books, I read articles, I talked to people who were current GCs and former GCs, and there were a lot of themes that came out of that research. First of all, you really need to get to know the business. Second, you really need to develop relationships with people that you’re going to be working with, both vertically and horizontally in a matrix organization. Third, you need to recognize that the breadth of the practice is significant. You can’t be an expert in everything, but you have to have a good working knowledge in a lot of areas. I’d encourage people to go as broad as they can in their current position, whether in-house or in law firms, to make sure they really understand the dynamics that exist beyond their specialty.

I’m not sure that the general counsel’s skills are going to be radically different ten years from now. GCs are always going to have to know the business very well to be effective. They’re going to have to develop strong relationships with executives and with business leaders, and developing leadership skills is going to be critically important. Finally, where GCs are going to excel or not is in having great judgement and being able to communicate their thoughts into a rationale for what they’re discussing. Technology and tools will change over time, but those are just ways to do our job – the skills are going to be the constant.

I think in the future, routine work will be technologized and repetitive jobs will go away – and go away could mean offshore, it could mean go to non-traditional legal service providers, but it’ll likely not be done in-house or by law firms.

People use the word innovation a lot these days, and it means a lot of different things. People naturally think of innovation as connected to technology, and a potential value is that you can create data from experience, which can help from a consistency perspective. At Nielsen, we’ve tried different technologies and software from time to time, and we’ve also worked to create and implement processes to help make our work more efficient and more consistent. We’ve created model forms, knowledge management databases, and certain practices and policies which, coupled with training, teach our department and our internal clients how to accomplish their goals in a more streamlined fashion. We’ve also engaged RFPs in select areas, which has helped reduce costs significantly during a time when, as a company, our revenue has grown – which is a big win.

I think, in future, the pendulum will probably swing back and forth about whether legal departments grow or more work is outsourced but, by and large, my guess is that more work will be insourced. I think it’s ultimately more cost effective to have insourced work, and as you start to focus on paying for the highest value work – it comes back to judgement and expertise – you’ll go outside for that if you happen not to have that in-house, and you’ll pay for that. But you won’t pay for the lower-end work. You’ll either take that in or, more likely, you’ll outsource it to third parties who can do it more efficiently than a law firm.