Like so many others who hold the prestigious position of general counsel within the Fortune 500, Tom Sabatino’s career path began in private practice. Now the GC of Walgreen, which is worth $72 billion as the largest retail pharmacy business in the U.S., he is part of an elite group of serial general counsel who has served multiple tours of duty. Sabatino recently sat down with InsideCounsel to talk about his path toward the GC seat and the transformational journey his 110-person law department started on six months ago. Below is our full exchange.

Q: What do you like about in-house work vs. private practice?

I love the business side of it; I love being part of an organization that’s growing and being on the front lines. I would much rather be in this position than be a lawyer looking after the legal needs of the business. To me, that’s what’s exciting about being in house.

Q: What’s important to know about Walgreens and the work you do there?

We have a specialist pharmacy business where we provide specialty pharmacy products, and we have a large infusion business. Our lawyers are focused on healthcare issues, practice and medicine issues, prescription drugs, immunizations, and of course we have regulatory lawyers. People may not know, but when we acquired Alliance Boots, we were opening a store every 17 to 18 hours, and we had 25 real estate lawyers at one point. M&A is a big area of focus for us. Walgreen is a humble giant. We are a Fortune 30 company and are doing things that people don’t think of Walgreen as doing.

Q: Are there any specialized skills you’ve developed by working at a retail company, as opposed to another kind of company?

The thing you learn to do when you go into these different industries, especially as GC, is to learn the business very quickly. As you try to build the business, you learn what is the long-term runway for some of these long-term healthcare services we provide. It’s given me the ability to take what I learned in new companies and bring them to new settings such as how do you manage lawyers, motivate them and provide pathways for success. You quickly figure out what doesn’t work and what works.

Q: What is the most rewarding part of your job?

On the business side, it’s been putting our deal together with Alliance Boots [by purchasing 41 percent of the company] and combining a $40 billion global company with Walgreen in a very innovative deal. I have also been learning the retail business—it’s a very different business. I am someone who believes in continual learning and this role provides that, which is important to me.

Q: What has been your biggest challenge as GC of Walgreens?

When I started, the law department at Walgreen operated more along a traditional law firm model. We didn’t formally create connections to the business. In April 2013, we went through a law department transformation. We put our people into teams focused on certain areas of the business and doubled the amount of managers so they are true business partners. That has been a real challenge because you have to retrain everyone to think in a certain way. This has been a transformational journey.

Q: What advice do you have for inside counsel looking to advance to be GC?

What has allowed me to be in these roles is that I’ve been passionate about understanding what drives the business. If you are already inside, spend a lot of time understanding what drives the business and how you can bring value to the enterprise. Don’t neglect the people part as you move up the ranks within the law department. Don’t forget about things like commitment to diversity and advancing women. Ultimately, if you make other people better, they will lift you up as well.