If anyone fits the description of being “self-directed,” it’s Diana Chafey. She grew up in a military family with no lawyers around her, but decided in fifth grade that she would one day practice law. In her young mind, a legal degree was as versatile as they come—she could likely apply a legal education to any field she may decide to pursue.
During her senior year at Arizona State University, Chafey made another firm decision—she was going to live in Chicago. She had always wanted to move to a large metropolis and -after visiting the Windy City with a friend her senior year, she found the perfect new hometown.
Chafey took a year off after her college graduation to work as a paralegal at a big law firm in Phoenix, then headed to Valparaiso University Law School, about an hour outside of Chicago. Not surprisingly, her career flourished upon graduation.
Chafey moved to Chicago and landed her first job out of college as an in-house lawyer at Allstate Insurance in Northbrook, Ill.—a position that set her on a path of building a career in insurance law. While she learned a lot at Allstate, the commute from the city to the northwest suburb was brutal, and after a few months, she moved to Interstate Insurance Group, at the time a wholly owned operating specialty holding company group that was part of Fireman’s Fund Insurance Company. In that position, Chafey reported directly to the general counsel and handled a wide variety of matters. After four years at the rapidly growing company, Chafey’s supervisor was promoted—and at the young age of 27, she became the company’s vice president, general counsel and corporate secretary.
Today, Chafey is the executive vice president, general counsel and corporate secretary of The Warranty Group. Her journey from a 27-year-old general counsel to the seasoned in-house professional she is today also included a long tenure at one of the world’s largest law firms—an impressive career that is truly well-rounded.
What was it like to become GC at such a young age?
It was a tremendous learning experience, personally and professionally. The company experienced high turnover in the C-suite for various reasons during my eight years at Interstate, but somehow I managed to survive. It was also my first time leading and managing a team, which was challenging from many perspectives, including having to make some difficult personnel decisions over time. It did expose me to issues faced by many GCs everyday —that most people probably don’t get that early in their career.
Why did you leave?
Over time, Fireman’s Fund made it clear it was trying to cut costs and consolidate some of its operations, so it began moving the legal and compliance work to its headquarters in California. Fireman’s Fund left some support for the business in Chicago, but redundant functions were being eliminated. I reduced my team accordingly, and my scope of responsibility was being reduced. In order to further advance in the company, I would have to move to California, which did not appeal to me at that time
So you moved to private practice?
Yes. I had always enjoyed being close to and having the ability to influence business decisions while in house, and the entrepreneurial aspects of building a business and practice were intriguing to me. I started talking to one of the partners I had been working with on a number of matters at Interstate. At the time, he was at Rudnick & Wolf.
At that time, Rudnick was in the process of merging with Piper Marbury, another large law firm, and was not bringing on new attorneysuntil they got through that process. So, I went to Ross & Hardies for a little over a year, and when Piper Rudnick (now DLA Piper) was ready I joined the insurance and reinsurance practice. After two years, I was made partner. I spent 10 years at DLA.
What did you think of working in a big law firm?
The firm was generally very supportive of me and helping me build my practice over time. The firm itself grew exponentially while I was there, and by the time I left it was the largest law firm in the world, with over 4,000 lawyers practicing in over 60 offices worldwide. The firm’s international growth enabled me to develop a very international and diverse practice representing large international clients in transactional and regulatory matters. I had some really great clients. I had built a nice practice. And I wasn’t looking to do anything new when The Warranty Group position came across my desk.
How did you find out about The Warranty Group?
A good friend was looking for a job and came across the job description for The Warranty Group (TWG) GC position. She said, “I can’t imagine anyone more suited for this job than you.” In my last five years at DLA, I had started representing warranty companies so I was very familiar with the business. The company was also owned by private equity, and I had a number of private equity clients and portfolio company clients in my practice. In short, it checked all the boxes for me.
I have been at TWG for almost five years. And I can honestly say it’s the best job I’ve ever had.
How has your role evolved over the years?
The core business has not changed but TWG has changed ownership. I joined the company in April 2013, in part to help sell the business. We were owned by Onex at that time, a Canada based private equity group. Onex had been rapidly bringing in new leadership and getting the company ready for sale. So by that fall, we had hired bankers and began the process. In August 2014, we closed the sale of the company to TPG Capital. It was very exciting to go through that process on the inside—being a part of the senior management team.
Since I started at TWG, my team itself has shrunk in some places and grown in others because we have gotten more efficient in some areas and business has expanded in others. For example, the teams in Asia and Latin America have grown, but the team in Europe has become smaller. Today, my team total is about 42 worldwide, made of lawyer and non-lawyer legal, compliance and risk professionals
Here in the U.S., my group has become smaller because it was not a particularly efficient or high performing group when I started. I have addressed those issues over the years and I’m now proud to say my group is considered a valuable asset to the organization that helps the business develop compliant solutions and offerings rather than being the department of “no.”
That’s how you avoid problems. If you are considered a road block, the business people stop coming to you. That’s when bad things happen. In the five years I’ve been here, we have paid one minor fine and we paid it out for nuisance value despite being on the right side of the issue. In a highly regulated industry, that’s a great track record.
What are some of your biggest challenges?
Managing risk in a very complex business is one. Because TWG writes service contracts, insurance, reinsurance, provides administrative services and sometimes offers all the above to clients, it is subject to multiple layers of regulation in many countries where we do business. Managing risk in some of the high-risk jurisdictions where we do business is another. We worry about bribery and corruption in certain places. However, I do believe we have built a robust compliance program and a strong culture of compliance, which mitigates the risk.
What is a goal you have for your department in the next 12 months?
We announced in October that we are being sold to Assurant Inc. So, the primary goals for the next 12 months are to obtain required regulatory approvals to close the transaction and assist with integrating our organizations.
What do you love most about being an in-house lawyer?
You get to see the results of your contribution when you’re in-house as opposed to being at a firm. You also develop a deep understanding of the business, which enables you to give better advice. You’re working with other talented senior executives that you’re learning from every day. I also work closely with our board and developing these trusting relationships has been very rewarding.
Please tell me about the mentors you had growing up in your legal career.
Carol Newman, the GC who hired me at Interstate. Carol really prepared me to be promoted to a GC position at such a young age. She is tough, speaks her mind and stands by her principles . And that’s why she has been successful.
Carol is very creative and instilled in me at an early age that, as a lawyer, you can’t be a roadblock, you have to be a solution finder. She is talented at finding ways to help the business figure out how they can achieve their objectives in a slightly different, but compliant ways. That stuck with me and I instill it in my team now, too.
David Mendelsohn, one of my partners at DLA. David was the one I was working with at Interstate and brought me to DLA. He was always very supportive of my career and my business development efforts. He was a role model in that regard and I learned a lot from him about how to sell legal services.
Colon McClean, our chief human resources officer here at The Warranty Group. Colon is by and large the most talented CHRO I have ever seen, and he has really helped me through some difficult personnel situations. I am also a better manager and leader as a result of working with him.
Tell me a little about your life away from the office.
My husband and I have two four-legged furry children. Stella was a rescue so we aren’t really sure what breed she is, but think she is some sort of lab-shepherd mix. Stanley is an a pixie bobcat—and he literally looks like a bobcat. He has very dog-like personality traits so is a good companion for Stella.
We live one block from Wrigley Field and we’ve been in the neighborhood for 18 years. We’ve been Cubs season ticket holders since 2003, through the good and the bad. When the Cubs went to the World Series in 2016, we were able to go to all the games in the first series, two in the second and two in the World Series.
I like to golf in the summer if I have time. I golf less often than I used to because it’s hard to find the time. I’m also a scuba diver, so we occasionally go on diving trips.
What advice would you give a young lawyer who wants to be a GC in a large company someday?
Young lawyers who go into private practice or even large in-house legal departments tend to become specialized in one area of practice, but my advice is to get as many experiences as you can. Be a generalist because, as a GC, while you don’t have to be an expert in everything, you have to know enough to spot an issue.
Also, you have to assume that as a GC, you will likely lead a team. So don’t neglect developing management and leadership skills. Developing trust and loyalty among team members will be a critical part of your job, and will be necessary to build high-performing teams.