top of page
  • Writer's pictureJay Judas

Tier One Interview: Jane Riley

This month, Jay chatted with Jane Riley, Chief Compliance Officer at The Leaders Group. The pair discuss Jane's Yellowstone-esque family history, regulatory overreach, the importance of succession planning and where to eat in the greater Denver area.

JAY:    I am kicking off 2024 with an interview that might be considered ‘click-bait’ because it is with someone that just about everyone in the high-net-worth part of the life insurance industry knows of and wants to know more about.  Jane, thank you for participating and taking time from your oversight of over 1300 registered representatives at The Leaders Group.  Let’s start by hearing more about the life insurance industry’s leading broker-dealer and your role in the organization.

Jane Riley

JANE:  Thank you for inviting me to be a part of the Tier One Series.  The Leaders Group was formed 30 years ago to fill a void in the variable life distribution world.  We were the first broker-dealer to cater to brokerage general agents (BGAs) and the distribution side of the business.  As an accommodation to the agents working with the BGAs, we accepted retail registered representatives as well, and then some of those people needed a registered investment adviser for their financial planning and wealth management clients, so we formed TLG Advisors as an affiliated RIA.  When I joined the firm in 1998, we had about 100 registered reps and worked with about 30 BGAs.  Today we have close to 1300 registered reps and work with approximately 250 BGAs. 

I left the real estate world after my first son was born so I could have regular hours - and a regular paycheck - to join The Leaders Group as the office manager and network administrator, which meant I did a little bit of everything.  By 2001, we needed a dedicated compliance department so, by default, I become our compliance officer.  I had no idea what I was getting into! There is no “compliance officer training course” so I have had to build my own and I continue that journey today.


JAY:  It occurs to me that your childhood was a bit like the Yellowstone television series but with a lot less drama….and land!  I do not often get to ask an interviewee to start with their great grandparents when talking about their path to the life insurance industry, but I do today, and I hope you will indulge me by turning back the calendar to 1903.


JANE:  My paternal great-grandparents came to Colorado in a covered wagon.   My grandfather was a game warden, and my dad grew up in the mountains in the kind of life we can only dream about now.  My mother’s father “retired” at age 42 after selling an interest in a business and bought ranches in Northern Colorado.  My parents met and married, and my dad became the ranch manager.  Kind of like Rip on Yellowstone!  The ranches were sold when I was about 2, so we became town kids after that.  Only one of my brothers stayed in agriculture and the rest of us took business routes, with my brother Dave founding The Leaders Group after being an insurance specialist and branch manager for EF Hutton. While I was in college, I spent evenings cold calling for the EF Hutton office inviting people to seminars.


JAY:  When we last spoke, I thought we might have to toss around a few subjects that you frequently come across to find ones to discuss in this interview.  That was not the case.  When I asked you about your top concern, you immediately replied, “regulatory overreach.”  You were not shy with your thoughts on this area.  What do you mean by regulatory overreach and what impact is it having on the life insurance industry?


JANE:  I believe that people are basically good and want to do the right thing.  Unfortunately, regulators do not share that view and keep coming up with more rules to regulate behavior.  In my opinion the overreach really started with Dodd-Frank. While very well intentioned, Dodd Frank was written too quickly, and tried to be the quick fix to the 2007-2009 financial crisis by shifting decision-making from the private sector to regulators.  

In the decade since Dodd-Frank we have seen the proliferation of data privacy and security rules, suitability turned into best interest and now fiduciary rules, and now the emergence of AI rules affecting the industry.  All these rules increase the cost of doing business which is passed on to consumers in policy expenses.  If we could slow down the rulemaking, everyone could spend more time and money on the consumers.


JAY:   Your motto in your work as a senior compliance officer is “Doing the right thing is always the right thing.” When you think about your registered representatives, what keeps you up at night when it comes to compliance missteps?


JANE: What keeps me up at night is thinking about the unintentional mistakes that could have wide reaching consequences. Something as simple not fully disclosing all the fees and expenses could compromise the whole enterprise.  Our registered representatives all have office staff and families who would be affected by a misstep by one person.  That is what robs me of sleep!

JAY:   Lately, succession planning for our industry has been on the minds of many of your fellow Tier One interviewees. For a market where we ask others to plan their voluntary and involuntary exits from a business, we do not seem to be following our own advice.   At The Leaders Group, you faced the sudden death of your CEO and brother, Dave Wickersham, in 2020.   How did your organization deal with that situation and what advice do you have for others in our industry based upon your experience?


JANE: That is so true!  We were very lucky that Dave had been delegating most of the day-to-day operations to the executive team for a couple of years.  We were able to come together as a team and learn to count on each other for expertise and make collaborative decisions. 

What we learned is that no organization can be dependent on one individual and that teamwork and mutual respect are critical to making it through a crisis.  Having a continuity plan, even if you don’t have a succession plan, is crucial.  On the individual agent level this could be as simple as identifying someone that will service clients in the case of death or disability.  On a corporate level it may mean having good job descriptions and procedures so someone else can fulfill duties.

The most important first step is to imagine the unimaginable.  


JAY:   When you are not working and spending time with your family, you are very involved in volunteering in your community. I understand some of that may stem from having first responders in your family.  Tell me more about this.


JANE: I was raised to be community-minded and to give back, so I have always volunteered, everything from the Junior League to school committees to industry groups.  Public safety became a larger concern to our family with the number of school shootings in our community and their immediate impact on us.

My stepson lost friends in the Columbine shooting almost 25 years ago, and our two sons had a shooting occur in their high school 10 years ago.  That event pushed one toward Army service and the other to EMS and firefighting.  Our firefighter is married to a police officer, so we are very aware of first responders and public safety.  Both my husband and I serve on a public safety advisory committee in our community.  

JAY:  You are one of our Tier One interviewees who I feel makes me more popular by association, Jane!  Thank you for your time.  Speaking of popularity, we have reached our restaurant question and, according to our data, is where many of our readers scroll to first before scrolling back up to the beginning of the interview.  Without naming a steakhouse or a steak dish, share some of your favorite restaurants that I should visit and let me know what I should order when I am there.


JANE: My favorite restaurant in the Denver Metro area is La Loma in Castle Rock.  It is built on a hillside and overlooks this beautiful valley and the Colorado foothills. They have the best chile rellenos with green chile! And of course, you have to have a margarita to go with it.  When I am traveling, I love The Oceanaire in Washington, and any of the authentic family Italian restaurants in New York and New Jersey.


Since its inception, Life Insurance Strategies Group has solely focused on the individual high net worth life insurance market. We do not sell products. This allows us to offer unbiased, pragmatic advice. Visit us at


bottom of page