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As the first General Counsel of M Financial Group, Cheryl Tobin oversees all legal, corporate compliance and corporate governance matters for the company. She is also responsible for strengthening M’s government affairs capabilities. Here, in conversation with host MC Sungaila, Cheryl takes us across her interesting career journey—from law school to the insurance industry, and a longstanding in-house role at market leader Pacific Life. She shares the many opportunities that helped her grow professionally, including taking on a new role building an in-house legal department.

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M Financial Group

About Cheryl Tobin:

Cheryl (Cheri) Tobin oversees all legal, corporate compliance, and corporategovernance matters at M Financial Group. She is also responsible forstrengthening M’s government affairs capabilities. Before joining M, Cherylserved as Vice President, Counsel, at Pacific Life, where she led the teamproviding legal support for the retail and reinsurance operations.Active in theAmerican Council of Life Insurers (ACLI), she chaired the ReinsuranceCommittee from 2019 to 2021. At Reinsurance Group of America, she had avaried career, including heading operations and systems for RGA’s Argentinelife insurance subsidiary. Cheryl earned a bachelor’s degree from Tulane University and a Doctor of Lawdegree from Washington University.

I'm very pleased to have on the show the new Chief Legal Officer of M Financial Group, Cheryl Tobin. Welcome.

Thank you. I'm delighted to be here.

Thanks so much for joining. You have such an interesting career journey and we were discussing a new role in building a legal department at a company and also many years in-house prior to that. Not many people, especially those in law school, think about even in-house as a career and what you can do with it, especially in a very highly specific, highly regulated industry such as insurance. I wanted to start first with what drew you to the law or made you decide to go to law school.

I graduated undergrad with a French degree, so we all knew we had to do something.

Maybe move to France now?

Opportunity missed but whatever. I decided, “What can I do?” I tried an MBA course and was like, “This is common sense and a waste of my time. What else can I do?” I thought law school is the practical application of philosophy. How interesting is that? I also figured it would be very versatile because you can do pretty much anything with a Law degree.

I decided to go to law school and it is a fascinating course of study. It teaches people how to think in different ways. It teaches you how to find answers, and how to solve problems when it's not black and white, which I thought was different from the MBA programs that I had gone to. There always seemed to be an answer, and we all know that's not true in real life.

It turned out to be an interesting course of study. While I was in law school, I was hired at a local insurance company to help them stand up their variable annuity product and system, and I started coding their accounting tables. As I progressed through law school, they got me more involved with more legal-type things like drafting up product prospectuses and doing some of the regulatory work.

It turned out great for me. I get out of law school. There was a part of the company that I was working for had been out and gone public. It was their reinsurance company. They hired me and I was the only lawyer they had on staff. I got to do totally cool stuff that I probably had no business doing but I learned so much. I got involved in international stuff. I got involved in regulatory things. I headed up the HR department and built an HR department. I was doing contract negotiations, drafting, and leading the team. I got to work in Argentina. It was cool.

I was thinking two things about that. First, I was thinking, you have a deep, extensive knowledge of the business part of this starting in law school, and then a legal position into that immediately. This is not something that normally happens. The typical route, particularly to in-house is you go to a firm or do some practice, whether it's in government or private practice but at a certain point, you bring that experience and knowledge house for a company. That is a thing.

At that time, I was not that interested in a private firm position, mainly because I didn't want to deal with billable hours. I was interested in the business side of stuff. I found that very fun and it is fun.

Anyone who says the MBA is common sense is someone who has some business sense.

Let's be honest, I didn't get that far in the MBA program because I would've changed my mind once I got into the financial accounting stuff but here we are.

It reflects that there's some part of that isn’t a natural inclination of yours. I agree with that if you had an intro class to something that might not be the full depth of what people go through. The one thing I remember from business school at UCLA, which is right next door to the law school, is that we would have various breaks or you would see people out at the tables, the business, the MBA students were always working in teams, in groups at the tables, and the law students were always off on their own reading and doing their reading for the next class.

I thought, “They're definitely teaching teamwork.” I can see that they’re working on problems together and that's not the first thing you learn in law school. I thought there was something different that was being taught there and it was for a purpose and probably would've been helpful for the law students too but we were burning in our books. That's pretty cool. You're building this legal team and doing that work straight out of law school. That is amazing. Were you, at all thinking, “This is thoroughly unusual and perhaps this is more than I can handle,” or did you move straight ahead because that's what you had to do?

To clarify, the company was called RGA. I did not build a legal function for them. I did more of the business work. I built the HR department and managed what they called reinsurance treaties. It's the contracts for the company. I created that unit to help draft and negotiate those terms and get them recorded properly.

I went to Argentina and there, I headed up the operations and systems for a life insurance company. That was different from being in a legal position. However, while I was there, it was still when there was no individual life insurance in the country. In Argentina, it was brand new, so they didn't have the law and regulation around that. The ministry of the economy contacted me and asked me to help them draft the regulation needed for that part of the industry.

Being on the ground floor of an industry in a particular area where they're developing the framework, that's so exciting.

A little over my head because it was all being done in Spanish, while in French, there are a lot of commonalities, not the same, so I was at a bit of a disadvantage.

I'm onboard with the whole language thing. I had my experience with that when I wrote a brief for the Inter-American Court of Human Rights, and I noticed when I was asked to write this brief that there were various official languages of the court. One of them was English. Others were French and Spanish. I said, “To be clear, I'm not going to have to write this formal legal brief in Spanish because that I cannot do.”

They said, “You can write in English,” and then it turned out, the court wanted this whole brief, ultimately to also be in Spanish. I understand the feeling of, “What? How am I going to do that?” I had to get someone to translate and submit it. It's very different. It's not your conversational Spanish at all either. It's highly formal. You were doing business functions for the company but also it sounds like some legal policy stuff, which is interesting. When did you switch over to in-house legal work?

After I left RGA, I came to California and got a job at Pacific Life, and started in the compliance role. As I was there, I was working with the annuities, and mutual funds division, and the company was a target for a class action lawsuit involving the annuity products. I got to work on that lawsuit and through that, I ended up in the law department at Pacific Life and then started doing purely legal work. For me, it is extraordinarily helpful for in-house lawyers to understand the business because you cannot provide good advice and guidance and help your business partners unless you understand what they're doing, why they're doing it, and how to get them to where they want to go.

When you were saying you started and were involved in the business functions of an insurance company, I thought to myself, “That is so valuable because that's always in an in-house perspective.” Offering legal advice, you want to make sure you understand the objectives, and how the business operates, all of that in rendering that advice as an in-house counsel. That gave you such a leap ahead of many other people who would still need to learn that. If they had the legal knowledge, they'd need to understand the business side.

Even negotiating contracts, when you're negotiating contract terms, it helps to realize, “I don't know if we can do that. It sounds great. We should be able to do that,” but in real life, may not work quite as this is drafted, and so you can get terms in place that makes sense for the company and avoid inadvertent footfalls.

That sounds like a great thing, but logistically, regulation-wise, or whatever it is, that's not going to be something that will work. Did you have different roles at Pacific Life then? You were at Pacific Life for a long time.

It was for a very long time. I was there for nineteen years, so I moved out of the compliance role into the law department and got involved with providing day-to-day legal support for annuities and life insurance divisions and managing litigation. I was doing arbitrations and did a lot of the reinsurance work myself because of my prior experience at RGA.

I was eventually put into a management position, so I had a whole team of attorneys and paralegals reporting to me. We did review intellectual property, product tax, and the gamut of stuff. I also started getting involved in government relations work, which is super fun. I started being a participant in some of our industry associations and then getting involved in specific topics of interest to the company and advocating our position on certain things that were pretty contentious in the industry.

That's always interesting. That harkens back to what you were talking about in the beginning in terms of the government policy work, which is a whole different animal as you mentioned. It’s neat because it gives you this overarching view of larger issues that the company and the industry are facing, and then being proactive about that instead of putting out individual fires as they come up.

It's cool to work with people from other companies and work with regulators and lawmakers and then see some of the things that you are responsible for showing up in statutory language. There's nothing better than that. It's fun.

It's amazing to see it. Maybe we'll talk about your new role and then we'll get into the overall mentoring and advice for those who might consider in-house. You left Pacific Life, and now you have this new role as Chief Legal Officer at a new company. Maybe you can talk about that role a little bit and what you anticipate doing in the short-term since you’ve just started at this point.

I'm psyched about this opportunity. I started a few months ago. I am the first general counsel for this company that's been around for 40 years, and I am now responsible for building a legal, corporate compliance, government relations, and then corporate governance function. It’s fun and I get to bring everything I've ever done comes in here. I'll get to tap into everything and everybody I know to get this done. To start at a high level in a company and to know I have an opportunity to make a difference, have an impact, and help this company and our clients grow is a very exciting prospect. It's daunting.

We've got a lot of work to do. Our industry is highly regulated. We're regulated by all the states individually. We have got Federal Regulations in the form of the SEC and FINRA, and we're dealing with people's money. We're dealing with retirement savings, wealth transfer, and all the things that are incredibly important to people's well-being.

Deservedly well-regulated but we're all people. People make mistakes. Putting into place the different guardrails, the different processes, and procedures to help our company and our clients navigate is going to be a worthy cause. I see this as in-house counsel, and this is true for all in-house counsel. Our job is to get our business to where it wants to be safely and to provide a well-reasoned balance of risk-reward so that people enter into whatever it is they're going to be doing with a good understanding of what the risks are, how we might mitigate those, and what to look for.

The government relations piece, for me, means I need to keep my finger on the pulse of what's going on in our industry, what regulators are thinking about, worried about legislators, and looking around the corner to help our business people know where to go and how to get to where they want to be. We've got a whole new executive team, so it is a new day for all of us. We had our first offsite meeting. It’s exciting. We've got good leadership, and very talented, bright people. A lot of hard work but great stuff ahead. I'm thrilled to be in this position and to have this opportunity.

What you said is what I was thinking at the beginning and the theme that I've seen across a lot of the guests’ own professional lives, which is having all of the particular skills knit together and fitting perfectly for a particular opportunity at some point in their careers. You could think, “This person is the person to be doing this based on their experience, their particular skills, their personality, all of that.” It's always exciting when that all converges and you're like, “I can contribute because I have all of these different threads together, and very few other people would have all of that.” It's neat.

You're at your highest and best use because you are applying all of the particular threads. Although daunting but it’s exciting to be building that department and function. At some point, we think about our legacy as well as what we are building and providing for the company in the future, for our clients, and the next generation. It's neat to be positioned for that. I'm going to circle back to the advice part. For those who are in-house counsel are interested in that particular role, what advice would you give to those who are first, entering it? What skills would they need to do that, or how would they maximize their opportunity of going in-house?

For me, what has been very helpful is that I'm naturally curious. I want to know. I am not happy tucked into the corner going through whatever task has been put before me. I want to know why I'm doing it and how this fit into the big picture. It makes a big difference if you understand why you're doing whatever it is that you're doing. That allows you to be more creative.

It makes a big difference if you really understand why you're doing whatever it is that you're doing.

It allows you to say, “If we want to do X, then what I've been told to do will get us there but there's a better way.” It's more interesting to understand the industry or the business. I've never been very good at staying in my lane. For some firms and companies that may not work, predominantly, if you're in an older company that's been around a long time, they have areas that they need people to focus on, and they're not going to be as interested in people going outside of their lane.

The further up you get into an organization and the more people you meet and talk to, the more you get to do and the more you get to expand your knowledge and your areas of practice. Several years ago, if you had told me that I would be working on industry issues and talking to regulators, and advocating for a position, I would've been stunned.

It’s because of the way I operate and understood we had this issue that we were trying to solve, we go through this process and it turns out to be something that the industry overall was a path many of us had taken and the regulators didn't like it. It also became a competitive issue. There's all this stuff going on. I was able to get involved at that industry level because I had done more than just draft my documents or file my reports. I was involved in the conversations about, “We got this problem. What do we do about it? How do we think about it?” That's the other part, not only being curious but talking to people.

Talk to the people who are doing the work, who understand the business, who know what you want to know, and who get involved in industry associations. You don't have to be immediately productive there. Everybody has to start somewhere. You go and start listening, you start talking to people, and before you know it, here you are, talking to regulators and getting stuff done.

Everybody has to start somewhere. So, just go and start listening. Start talking to people. Before you know it, here you are.

It's interesting when you said to be curious. It's a particular curiosity or interest, which is being curious about the organization and the business. Also curious about legal aspects but being curious about how functions in the company so that you could help facilitate that and maybe do things better, more efficiently from a legal standpoint and being informed. In a contract term, logistically, that's more of a problem. We should structure it in a different way.

I think of myself as a business person with a Law degree. That Law degree has given me this incredible toolset that nobody else on the business team has. That allows me to contribute in a different and more effective way than I would otherwise be able to do. It's a very valuable skill set to have.

As you mentioned earlier, which is the case, too, and I've seen it with various guests who we're not practicing law but are using their legal training was that critical thinking, the way you analyze and break down problems, and all of that is something that comes from the legal training.

The whole thing about there is not one answer. There are a whole bunch of different ways to look at something and get to where you need to be.

There is not one answer. There are a whole bunch of different ways to look at something and get to where you need to be.

I've even seen that serving on boards for various nonprofits. All these amazing people, CEOs, and business leaders who are on the board and it'll be the lawyers who say, “Let's find the nub of the problem, break it down, and here's what we need to address.” People will look at you in shock, like, “We couldn't see that,” and you think, “There is something to this legal training and thinking.” We break stuff down.

Identify what's important. There's a lot of noise out there. To be able to zero in on what's important and what the crux of the issue is extremely helpful.

It comes out in different ways. I don't know that you value that until you've been in those positions and you go, “I did learn something.” People always say, “We're teaching you how to think in law school and it's not just analyzing cases. It is breaking down problems.” What about mentoring and sponsorship? I like to talk about that because students often are told, “You need to get a mentor,” and they go, “Great. What is that? How do I go about doing that?”

They look to formal mentoring programs and pairing up and things like that. That's certainly one way. I also think that sometimes people may not realize when they are being mentored in small ways or being helped in enhancing their skills. What examples do you have of mentorship in your career and what has that looked like for you?

That is such a great question because I fell into that trap too. It was like, “I need a mentor. I've never had a mentor.” Of course, I've had mentors. I just didn't know it at the time. These are the people who, when you show an interest in what they're doing and why they're doing it, are more than happy to engage and help you learn the ropes of whatever it is that you're involved in at that time. I've been very fortunate. I've had the opportunity to be exposed to a lot of different people at a lot of different levels, both within the organizations I've worked for and also in the industry.

I've never planned for having a mentor. As I said, I didn't recognize when I was being mentored many of the times that it was happening but I sure did benefit from all these informal relationships. I've had few mentors. As I think about it, I would consider who is purely legal. They've all been from all walks of life. It's engaging with other people.

I think about the mentorship too, in terms of now that I see how decisions are made and they're made in rooms where you're not that certain. Somebody said something positive or moved something along in your direction, and you would never ever know that, and they may never tell you that they did it either. It's the kindness and generosity of people who help in that way. As a result, because you don't always know who it was that mentored or helped you, the best thing you can do is pay it forward, mentor, and help others.

There is a danger of, especially starting, there's a lot of competition and that can get in your way. I know it has gotten in my way. It's not a zero-sum and I'm embarrassed for how long it took me to figure that out but whatever. I got there. For me, it's being candid, being transparent is very helpful to others. Diplomacy is helpful, and tact would be good but we do what we can with what we were given to work with.

If somebody approaches me and asks me anything, I will give you my honest feedback on that, and hopefully, it's helpful so that I don't have a formal approach to mentoring. It's not like I can say I have a mentee but I can do that. I've helped a lot of people over the years. Not with that specific intention but

that's how you get things done. It's more fun to live that way, to engage with people and be honest. I have been humbled by the number of people over the years who've told me, “You helped me.” I'm like, “I didn't know. Great, I'm glad.”

It's nice to know that sometimes you don't know. You're being yourself, doing what feels right for you to do and helping others. If you took a leap of faith and confidence in yourself in moving into your new role, do you have any tips for those who might be stepping outside your comfort zone? Any tips on being able to do that?

I have made a career of stepping outside my comfort zone. It has always turned out great. I remember a friend of mine who was opening up an office. This was in Argentina. It was the MTV office and people are running around going crazy. Someday, she was telling the story, “People are running around with their hair on fire and I finally said, ‘Stop. Nobody's going to die.’” That puts perspective on things. Nobody's going to die. What's the worst thing that can happen? If you fail, so what? You pick yourself up and move on. There's a wonderful thing on YouTube that was making the rounds. I can't remember the guy's name. Admiral was somebody who'd given a commencement speech. Do you know the one I'm talking about?

Yes, I do. Is it McRaven?

I think so. It is excellent and talks about, “You will fail.” I guess I will. I also think a lot about people who are in public positions and we've all seen everybody in these high-profile, high-visibility positions fail. It all turns out okay, nobody dies. Everybody lives to see another day and can succeed going forward.

I love that anecdote about your friend in Argentina. I think about that, “This is difficult but nobody's going to die.” Let me put it in perspective. “That's not going to happen.” “We'll deal with it. One step time.”

This comes back to legal training too though because we are taught to think about, “What is the worst thing that could happen? How can this go wrong?”

We're always thinking about that, like, “What's the downside? What's the risk?”

In doing that, there's a way out. There's a way forward. You're never stuck there.

That's true. We get a lot of flak for that. We see the downsides, the negatives, the risks, and sometimes the business side will say, “That means you don't want me to press forward with this thing.” It's like, “That's not true, but maybe there's another path that will be better overall.” Thank you so much. I appreciate that because I thought there were some people who are not comfortable with that. They're not comfortable with taking those risks and personal risks on themselves in their own careers.

I thought it was a good opportunity to ask about that. I appreciate your joining and talking about your career and experiences. I've gotten a good business sense that an in-house lawyer has and what fun that is to include that with legal advice and legal practice. It's different from being in a firm, outside firm in that regard to some degree, and also being part of an ongoing concern. You have one client and you're focused on that client doing well and doing well in the business and from the legal side also. That's another distinguishing factor about in-house work.