Starting Out

To read the full interview with Karen Klein, click here.

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Karen Klein is general counsel of Kayak.com, an online travel search engine that enables consumers to compare prices offered on other Web sites. She talked to InsideCounsel about her career path and gave advice for others thinking of an in-house career.

Q: When and why did you decide to become a lawyer?

A: I was 11 when I told my parents I wanted to be a lawyer. I drew up a contract outlining the allowance I thought I should receive in exchange for my chores. And at my law school graduation my mother actually gave me a framed copy of it.

I'm not sure what attracted me to law. I did not have family members or anyone I knew who was a lawyer. Luckily for me, a lot of the characteristics and skills that are needed to be a lawyer are things that I had, but I can't explain why I got interested so young. But I continued on that path and fortunately I ended up liking it.

Q: After finishing law school at Chicago-Kent College of Law, you went to a law firm, right?

A: Yes, I went to Katten Muchin and spent several years working in the M&A and securities group.

Q: Why did you decide to go in-house?

A: I hadn't been thinking about an in-house position. I was happy at the firm and I liked the work I did. But I did realize that there were a lot of things I worked on during deals that I missed when deals were over. Rather than hopping deal to deal, I really liked learning about clients' businesses. Then a deal would close and it was time to move on, and I felt like I had all this knowledge about a business and didn't have anything to do with it once the deal was closed. So going in-house was appealing to me.

One of the former mentors I had had at the firm had gone in-house as the general counsel at Platinum Technologies and offered me a job 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 [in the 1990s]. I had no technology background whatsoever. As he viewed it, there are a lot of concepts from M&A--negotiations generally--that are transferable. His view was that if you are a smart person who understands the concepts of business negotiation, we can train you on the technology piece. That was very fortunate for me.

Q: What is the strangest legal issue you have had to deal with?

A: When I first came into a business that is consumer-oriented, I found issues that were surprising to me. Dealing with a Web site, you see customer response to issues as strange as someone realizing that their kids took their credit card and booked a trip. Do we have a contract with these people or not? The children are underage, were they allowed to book this trip? Things like that that I had certainly never seen. You do see some strange things come across your desk in terms of consumer issues. But it's also part of what I like about the job. I like solving consumers' issues and problems and making sure we are giving them a Web site that serves their needs. So some strange things come out of it, but also some of the best and most rewarding work.

Q: What is the advantage of using Kayak.com over using another travel Web site?

A: What we allow people to do is to see a wide variety of choices. Consumers want to know, have I seen all the choices that are out there? Have I looked everywhere? Should I book this? So we give them the confidence that they have seen not only the prices that are available on an airline site, but also those available through an online travel agency like Orbitz. And then we give them the choice of where to book and we don't charge them any fees. More than anything, it's a search engine that allows them to find the best deal.

Q: What advice do you have for young lawyers who might contemplate an in-house career?

A: The best thing you can do is work on several of your core skills as a lawyer. Your ability to understand the numbers is very important--if you are going to work in-house, you have to understand what the revenue impact is of any decisions you make. Also work on your communications skills--a lot of us learn at law firms to deal with other lawyers. But you need to learn to interact with and work directly with and communicate with business people in a way that requires putting things in layman's terms and learning about the business. You have to understand the business issues because often it's about risk management, not risk avoidance.

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Mary Swanton

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