Cars.com chief legal officer Jim Rogers has a knack for helping companies through major transition periods.

The Columbia Law School grad spent nearly three decades as a partner at Latham & Watkins before retiring from private practice and joining the in-house world. He went on to serve as senior vice president, general counsel and secretary of travel website Orbitz Worldwide Inc. and saw the company through a $1.33 billion merger with Expedia Inc. in late 2015.

He joined Cars.com the following year, as the Chicago-based tech company, which operates a classifieds website for car buyers and sellers, was headed toward a spinoff from its parent company. Now, he's helping Cars.com negotiate a potential sale.

Rogers, who will be on a SuperConference panel on May 21 in Chicago, spoke with Corporate Counsel about being U.S. Supreme Court Justice Ruth Bader Ginsburg's law clerk, keeping legal department costs down, complying with data privacy regulations and his first car. This conversation has been edited for clarity and length.

Corporate Counsel: Let's start by going back to 1980, when you clerked for the “Notorious RBG.” Can you tell me about that experience?

J.R.: She wasn't so notorious then. She'd been a law professor of mine at Columbia. It was really terrific to see her settle in so quickly to the life of being a judge. I've learned a lot from her as a law student and clerking was a very intense experience. I learned a lot about the law and writing and rigorous thinking and collegiality as well.

CC: After your clerkship, you went on to spend the next 28 years in private practice. What spurred you to leave that world and go in-house in 2010?

J.R.: The practice of law had changed rather dramatically from the time that I'd joined Latham in 1981 until the latter part of the 2000s. In particular, it used to be that in-house counsel was sort of a sleepy backwater, not doing a lot of the interesting and challenging things, which were really done by the outside law firms. But as the years went by, things changed quite a bit and the role of in-house counsel became much more significant, much more strategic. A lot of the things we used to do as law firms were now being done in-house. At the same time, the role of outside counsel was becoming increasingly specialized, in part because you had such great generalists in-house. The role that I'd often enjoyed in the '90s of counseling these companies as they took on venture capital and went public was more and more being replaced by the in-house counsel. I realized that I wanted to have a longer term, more in-depth and strategic engagement, and that was in-house. So I took the rather bold step of retiring from Latham.

CC: Tell me about the role you played in helping Cars.com with its spinoff from its parent company in 2017.

J.R.: Both leading up to it and following it, it was creating a whole legal infrastructure around being a public company, including helping to negotiate the terms of the spinoff on the company's behalf. We oversaw the senior credit agreement. We took on a $900 million credit facility. All the corporate matters in terms of getting entities set up and electing officers and directors. A whole lot around executive compensation, establishing plans, making equity awards. We also set up an employee stock purchase plan so that people could be purchasing stock later. It was a whole variety of things.

CC: I understand that you've been busy exploring a potential sale of Cars.com. Can you tell me anything about what's happening behind the scenes?

J.R.: I can't say a whole lot, for public company reasons, but late last fall in response to a couple of inbound inquiries, our board decided that we should conduct a review of our strategic alternatives, including a sale of the company. And so we worked with our bankers and lawyers to develop a set of parties that we could reach out to and we have for some time been engaged with multiple parties. That's all that we've disclosed. We haven't announced a particular timetable or outcome for that matter. But it is very interesting, exciting and time-consuming from a general counsel's perspective.

CC: What are some of the most effective things you've done to keep costs down for your legal department?

J.R.: Cars.com had a relatively low legal budget, not a lot of outside counsel spend, when I joined. It certainly increased because we were going public. The biggest single thing you can do is see how much work you can get done in-house. Secondly, choosing firms that are good and work with you effectively and efficiently. On top of that, we've done a little bit of alternative fee arrangements. We engaged my old firm, Latham, as our corporate securities counsel and negotiated a fixed fee, structured for our day-to-day securities work, for the first year. That was not only predictable but it was also quite cost-effective.  

CC: What are the most frustrating aspects of your job?

J.R.: What's both frustrating and exciting is the sheer volume of stuff that comes across your desk. Most every GC will tell you that you come in and you have a list of things you want to get done that day and at five or six o'clock you take a look and realize that you haven't gotten to any of them because all of these things came up during the course of the day.

We also don't always have all the tools we'd like to watch outside expense, a lot of the fancy software and other kinds of products that could make some things a little bit easier, although generally we're pretty good there.

CC: Are you affected by the EU's General Data Protection Regulation and what have you been doing to prepare for the California Consumer Privacy Act?

J.R.: We spent quite a bit of time getting comfortable with the fact that we were not required to comply with [GDPR] at all, which is a little bit counterintuitive because it seemed like everybody and his brother was busy running around saying we've got to take care of GDPR stuff. But our business is purely domestic.

We are very interested and concerned about California. We are, at this point, at a very low profile of data information. People don't transact on our site. Most of the people who visit us don't sign up and give us their email address. We don't tend to have credit card information. And we certainly don't have other financial information that would subject us to the highest levels of scrutiny. Over the course of time that may change as we move into what's referred to as digital retailing, enabling people to go much further in the shopping process. We are about to sign up with a third-party vendor that is extremely helpful in this regard to help make sure that we're doing what we need to do for California compliance.

CC: I understand that you're an avid cyclist who bikes to work everyday. Does this raise some eyebrows at Cars.com?

J.R.: No, not at all. We're a tech company that's located right in the heart of downtown Chicago. Lots of people commute by train. But there are also a lot of folks here who are bikers. And I still have a car and I enjoy driving a car, when appropriate. You know, the CEO is a big cyclist himself. He's often calling us when he's on his Peloton.

CC: What was your first car?

J.R.: A Volkswagen Dasher, which I think is what became the Passat. My dad had bought it in Germany when I was a student in college, and I didn't know what it was because in Germany they called it by a different name. After college, I bought it from him at a very favorable rate.

CC: And your dream car?

J.R.: My dream car would be a fully electric BMW convertible with a retractable roof. But it doesn't exist yet.

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