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  • Writer's pictureJay Judas

Tier One Interview: Andrea Dykes

In our latest Tier One Interview, our CEO, Jay Judas, spoke with Andrea Dykes CFP®, Managing Partner of Howard Insurance, a private insurance advisory and risk management firm. The two discuss challenges and opportunities in life insurance today, how to attract more women to the industry, LIRPs, and walk through a day in Andrea's life. Read the interview in full below.

JAY: A selfish reason behind the idea for these Tier One interviews is an excuse for me to sit down with the top talent in the life insurance industry who I have wanted to learn more about. You have been high up on this list for a number of years. I’m sure it is not a surprise to learn that when I did my background research to prepare, three people who know you well separately asked what took me so long to get to you. Talk about pressure!

You’re a rising star in our industry, an athlete, a parent of three and a philanthropist so we have a lot to cover. First, tell me about your firm in Chevy Chase, Maryland, Howard Insurance, and your role in the organization.

Andrea Dykes - Howard Insurance

Andrea: It is a treat to be asked to be interviewed! Howard Insurance has been in business since 1945, though we have experienced tremendous growth and evolution as a brand over the last two decades. Historically, the firm specialized in high-end property and casualty work for business owners, real estate owners, successful families, and multi-generational wealth.

However, because clients trusted us for our sophisticated planning and advice, they inevitably demanded we handle all aspects of their insurance, which is how I came to Howard to oversee and implement recommendations for life, disability, and long term care insurance. Howard is uniquely positioned to manage virtually all of our client’s insurance and risk management in-house, and we have developed specialized practice groups within the firm that all work together to deliver the best outcome for the client. As managing partner, I lead our life insurance team and manage the firm’s business development and brand strategy.

JAY: Fill me in on your upbringing, education and how you found your way into the life insurance industry. I know you were a star athlete and remain a very good basketball player so I’m guessing some of the skills you learned on the court have translated to your professional life.

Andrea: I was born in Rockville, Maryland, which is about five miles from where I live today. I have two loving and supportive parents, and a smart and witty younger brother. Growing up, I absolutely loved competitive sports and I played basketball, field hockey, and lacrosse in my formative years. Being a part of a team is hugely gratifying for me. I love working together towards an end goal - Winning! - and as a natural leader, I enjoy taking the team down the field or court to victory. Good communication, trust and hard work, are skills on the court that are critical for my work today.

Howard Insurance Team Golf Outing

Since I capped out in stature at five feet tall, I eventually set aside my ambitions to play in the WNBA and found a career in the life insurance industry! I double majored in finance and economics, and while in college, interviewed at a few insurance agencies back home. I chose MassMutual, because at the time, the General Agent was a woman, my sales manager was a Black woman, and the office had an unusually high and welcome number of women agents. Having a woman leader and being around the company of women is both inspirational and comforting, and was absolutely the driving factors for my decision then, and what I want to see for the industry today. Knowing you, Jay, I’m sure you will ask me more about this later!

JAY: You are comfortable with any number of complex life insurance planning techniques and constantly work with both individual and corporate clients. What does your practice look like and what problems are you typically solving?

Andrea: My practice is built primarily around clients with busy lives and more complicated insurance needs. Most of my clients are focused on family, business, and charitable endeavors, so they rely heavily on my team for recommendations and management of their complete insurance portfolio.

Many of our clients own closely held businesses and large portfolios of real estate, which makes up a large concentration of their overall wealth, so their problems are focused around their illiquidity. We use life insurance to provide liquidity as part of a wealth transfer strategy or for estate tax planning purposes. Other problems our business owners come to us with are the challenges of growing the business and ensuring the value of what they have built passes to their family at a planned exit, or if they pass away. We also use life insurance for retention of key people who help grow the business, and for funding of buy-sell arrangements and other business succession planning to ensure the client’s goals are met.

For our families and clients without any substantial business interest, their problems are mainly around the complexities of their overall estate. Our team applies insurance solutions to help them efficiently accomplish their goals, be it passing wealth to the next generation, making charitable gifts, or paying taxes.

Some post "office Olympics" drinks

JAY: Word on the street is that you have executed a number of LIRPs for clients. When I heard this, I knew I had my technical question! What exactly is a LIRP and where do you see it best applied?

Andrea: A LIRP is a life insurance policy that is designed specifically for cash value accumulation purposes. It stands for life insurance retirement plan. When properly designed, the life insurance policy can provide tax deferred accumulation and asset protection, among other benefits. We have executed LIRPs for clients who are already maxing out their contributions elsewhere, and they like the idea of a portion of their savings in life insurance as a separate asset class.

JAY: There are an increasing amount of challenges in the industry right now. I’m sure I’ll be mentioning low interest rates for years to come but there are many others. We have a lot more private equity interest in both life insurance companies and distribution, we are seeing life insurance companies sell off blocks of in-force business and this raises the alert for cost increases for policyholders and we are witnessing a push by technology companies to sell policies to younger people without any planning considerations. What are you doing to navigate all of this?

Andrea: Indeed, there is quite a bit of excitement in the industry these days! For me, keeping abreast of the issues, with the goal of providing better advice to clients, is always paramount. These challenges are real, but often come with opportunity. For example, the low interest rate environment has brought challenges to insurance companies and, at the same time, has brought tremendous opportunity to clients for planning. As a rule, I generally navigate change using my moral compass to work in the best interest of the client. This has always worked well so why change things now?

JAY: Let’s talk about the elephant in the room which, really, is you and other female producers! While it is better than it used to be, why are there so few women in client-facing sales roles in the life insurance industry? Any advice on how to attract more women to our world? My husband passionately believes that having a career mentor or benefactor makes all the difference in most professional roles.

Washington Area Women’s Foundation Leadership Luncheon

Andrea: I agree with your husband, Pete, wholeheartedly! Having a mentor made all the difference for me as I navigated the early stages of my career and I still rely on my mentors today for sound advice. But to attract more women to the industry, we need a more inclusive industry and more women at the top. As I mentioned earlier in the interview, I joined a woman-run organization early in my career, primarily because I could visualize my success there and being in the company of women made me feel more welcome.

There is something to be said about the power of images, which are almost entirely socialized ideas about “men’s work”, which prevent women from being exposed to male-dominated industries. If our industry is serious about the issues we have around gender, we should set goals to target gender representation at the leadership and Board level….and then promote! Oh, and a few less steak dinners, cigar events, and freezing cold meetings in conference rooms, might help too. I know you also cringe, every time you have to go to a steak house in our business!

JAY: You and your husband, Jeremy, have three kids and you both dedicate a significant amount of time to charities. If I am not mistaken, you are involved with the Washington DC Area Women’s Foundation and the Washington DC Women’s Leadership Initiative. Walk me through a typical day.

Andrea: A typical day involves waking up before the kids to exercise. The big kids come down to the gym to find me, and they like to ride scenic routes on the Peloton once I’m done! After getting everyone dressed, fed, and ready for the day the nanny comes to help with our youngest daughter and I’m out the door for work. Of course, today’s “out the door” is a bit different but I’ve adjusted to the new routine of virtual team meetings, client calls and zooms.

I also try to build in time each week for something philanthropic and volunteer related. That could be participating in a nonprofit board meeting, fundraising for nonprofits, or something more informal like a mentorship call with a newer advisor in the business.

I tend to end my workday early enough to get the kids to their socially distant after school activities and put dinner on the table. I love to cook, so dinnertime together is the highlight of my day. After dinner, it is the banal routine of homework, showers and bedtime for the kids. Jeremy is a pediatrician, so I may use the excuse that “he’s a professional with children” to pawn off some of these tasks, in favor of quietly reading for a bit and or perhaps watching something mindless on Bravo. Anyone who knows me well wouldn’t dare text or email after 930 PM- they know I’m practically asleep!

JAY: You’ve made it to the restaurant question, Andrea! By now, you know how this works…except that I have dropped the ‘business meal’ part. What are a couple of your favorite restaurants and dishes? Remember, no steakhouses or steaks which are so prevalent in our industry.

Andrea: Naturally, I’d like to spotlight some DC favorites with women at the helm: pasta at Centrolina where you will find Chef Amy Brandwein; Jamon Iberico and all the Spanish cheeses at Maria Trabocchi’s Del Mar; and while technically a steakhouse, I must add St. Anselm, because Chef Marjorie Meeks-Bradley’s buttermilk biscuits and country rib pork chop are definitely worthy of mention.

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Read our companion Tier One blog by clicking here.

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


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