Karen Klien

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In the mid-90s, the technology industry was booming. Karen Klein was racking up lots of experience in dealmaking in the M&A group at Katten Muchin Rosenman, with no aspirations to go in-house and no background in technology.

All that changed when one of Klein’s mentors left the firm to become general counsel of one of its largest clients, Platinum Technology International Inc., a Chicago-based software company. He offered her an in-house position and the opportunity to train to be a technology lawyer.

“That seemed like very good timing given what was going on in the industry overall,” she recalls. “So it was a little bit lucky and a little bit fortuitous that I ended up a technology lawyer. I was very fortunate to have a mentor who was willing to take the time to have me work with outside counsel on the technology issues until I really understood them. That set the stage for the rest of my career.”

That career next took her to InstallShield Software Corp., where she was general counsel and corporate secretary. From there she joined the online travel agency Orbitz, at the time a startup, where she rose to be group vice president-legal, overseeing a staff of 13.

Now she’s back at a startup, as general counsel and the one-person legal team at Kayak.com, a travel search engine. Kayak allows consumers to conduct one search for the best fares and rates for their trip, consolidating information from hundreds of airline, hotel, rental car and online travel agency Web sites.

Q: What was your most interesting professional experience prior to Kayak.com?

A: I arrived at Orbitz shortly after they launched the site–when the company was truly a startup. We went from airline ownership to public ownership to being acquired by a Fortune 100 company to being spun off and bought by private equity, and then going public again a year and a half ago. The ability to see all that in the life cycle of one company in a period of six years was a learning experience like I could not have experienced in any other time period or any other business.

Q: How did you end up at Kayak?

A: One of the founders of Orbitz was one of the founders of Kayak, and he offered me the general counsel position. The opportunity to work with him again in a startup environment was a bit of a no-brainer for me, in addition to which it allows me to work from home–an added bonus I would not have expected to come with a GC position.

Q: What is it about working at a startup that is so stimulating?

A: First, the entrepreneurial nature of it. Because it is a startup, you are not sure what will come of the company or whether it will be successful or not. So there is a little bit of risk that makes it exciting.

In addition, it gets in your blood. You’re in an environment where people make decisions quickly, you move fast and people have a broader scope of responsibility than they would in a large corporation with many layers of management. You have that autonomy and an ability to feel like you are really affecting the business.

Q: You work from home in Chicago, half a country away from the corporate office in Connecticut. How does that work out?

A: I think for us it works very effectively. We are in the travel industry after all, and if need be, I am on a plane. But we are split up anyway. Our chief technology officer and the whole engineering team are in Massachusetts, our business team is in Connecticut and our sales team is in California. I am the only person in Chicago, but it allows me to go between the various offices as I need to.

Q: What has been the major challenge of your position at Kayak?

A: When I arrived (in November 2007), we had just signed a letter of intent to acquire SideStep, our largest competitor. So I spent my first six weeks working on that deal. It was an interesting first six weeks.

Q: What challenges do you face now?

A: Overall my biggest challenge is that we are still a startup, so we lack some processes. So for all these fabulous things about a startup, you are always doing triage. Your first priority is supporting the day-to-day business. And as a result, it is sometimes hard to find the time to go back and put processes in place.

Q: What legal issues cross your desk?

A: All types of contracts, dispute resolution issues. Because we are an online search engine, we have a lot of marketing and advertising on our site, so there are a lot of marketing and advertising copy reviews. I run HR for the company as well. Investor and shareholder documents because we do have a number of venture capital investors, many of whom sit on our board of directors. I manage our IP portfolio–that is an area where I use outside counsel extensively on both trademark and patent matters.

Q: What about litigation?

A: We’ve had one somewhat high-
profile piece of litigation, but our
priority is resolving disputes before they reach litigation.

Q: Do you see the legal department growing?

A: We really try to keep our company lean. We pride ourselves on that. So I would only add someone if I thought we were falling behind in supporting the business. Finding a way to balance the cost of outside counsel with our need to manage risk effectively is something I always keep in mind. And if I ever think the scale is tipping to where I am not able to do that effectively, that’s when I would hire someone. I haven’t hit that point yet.

Q: I read that all Kayak employees have to deal with customer service inquiries. Does that apply to you?

A: Yes, it applies to everyone. Customer service e-mails are randomly sent to every employee in the company. There is a scorecard on the wall at our office in Concord that literally tells who has answered how many questions per day, and the actual answers are displayed. We are expected to research the issue and reply to the customer with a personalized response and try to help them. As a lawyer, when I first came in it made me a bit nervous–the idea that everybody is answering e-mails, and is that creating liability? But I’ve come to see it as not only the right thing to do for the customer, but also good for our risk profile. Most people want an honest answer. If there was an issue, they want to know why there was an issue. By trying to fix it, you are staying close to your consumers and they are less likely to get upset with you.

Q: What has been your greatest professional accomplishment?

A: I’m most proud of having built a strong legal team at Orbitz. A lot of what we do as lawyers is not rocket science–it’s attention to detail. What lawyers do not learn in law school is how to manage people and work effectively as a team to support a business. In the end, I think I left a legal team that is among the strongest in the business. An added bonus is that we genuinely liked one another.

Q: What are your favorite travel destinations?

A: My favorite historical destination is Israel, an amazing place. My favorite scenic destination is the Dalmatian Coast of Croatia.