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  • Writer's pictureJay Judas

Tier One Interview: Jeff Wasserman

This month Jay sits down with Jeff Wasserman, Executive Vice President, Managing Director, Oswald Specialty Life, Oswald Companies. The pair talk about Jeff's career in the life insurance industry, the importance of relationships to a successful career, and how Jeff's dad shaped his career.

JAY: One of the reasons I wanted to interview you, Jeff, was that, from the outside, your successful career as a life insurance producer appears to derive from doing everything young producers are told to do at the beginning of their journey…and usually fail to do. You began with general agency training, found an early niche in the business marketplace, had an amazing mentor, and figured out a strong referral source. I think I may have oversimplified your past 38 years and I am looking forward to digging into those years today. Let’s start by hearing about Oswald Companies and your role with this employee-firm that has been around since 1893.

JEFF: I am glad to have made the cut for the Tier One interview series! My partnership with Oswald Companies began in 2003. At the time, joining a firm like Oswald felt like joining IBM to me, in size, as I was an independent agent with a salaried staff of two assistants and a case design producer working for me. At that time, Oswald had about 80 employees located in downtown Cleveland and was known in our community as the blue chip, a very well-respected, privately-owned insurance brokerage and risk management firm. They saw the benefit of having a designated life insurance business to round out their other three business units: P&C, Employee Benefits and 401(k) Retirement Planning Services.

So, a new partnership was created to bring me in their clubhouse, Oswald Specialty Life (OSL), which was owned equally by me and Oswald Companies. Our staff consisted of my two assistants, a junior producer and two internal employees at Oswald who also handled the life insurance the agency wrote.

The early years were terrific, lots of low hanging fruit and opportunities. GUL had just been introduced to the marketplace and we found many opportunities through our book of business, tremendous amounts of replacement and new planning opportunities.

After the first two years, business was much better than any of us had anticipated, and I was asked to merge my ownership of OSL into the Oswald Companies and I became a shareholder and an Executive Director of the agency. From that point forward we grew every year, adding staff to accommodate our growth and bringing on producers to serve our clients.

Today, Oswald is located throughout the state of Ohio, serving our clients in five of the largest markets in the state. We also have an office in Detroit, and through a merger with RCM&D, we now have offices in Baltimore, Washington DC and Philadelphia.

Today, we are a fully integrated risk management and insurance brokerage firm with multiple insurance disciplines with over 780 employees and growing.

JAY: You are a Cleveland-area lifer and grew up spending a lot of time with your father in his business…which was not the life insurance business. Talk about your upbringing and your path to, and through, the life insurance industry.

JEFF: My dad, Albert, was a wonderful father. However, if you know anyone in the retail clothing business, you know it’s long hours. My father’s business was open six days a week, so he was at his store most of the time. My father’s subliminal teaching of hard work, ambition and drive for success were ingrained in me at a young age.

Dad’s time spent with me as a teenager was working in his store and learning the art of selling clothing. I was taught to put together an entire outfit or wardrobe, not just a single pair of pants or shirt. Also, I was competitive with the other sales guys working the floor. I became pretty good at selling clothing but realized the retail clothing business was not for me! I felt if I could be successful at selling menswear, I would rather put my sales skills to the test of something more meaningful in life.

I was a finance major in college and was interested in a career that could educate and help families and business owners with money management and financial security. After interviewing with several financial-type companies - banks, brokerage firms and life insurance companies - I decided to take a job with Guardian Life in a general agency located in Cleveland. This was a very good learning environment to gain the sales and organizational skills, and discipline that became the foundation for my success.

The Guardian general agency was basically like a life insurance university where I learned what I needed about life insurance, disability insurance, annuities and the basic foundations of sound financial planning for families and businesses.

I was also driven to the independence and that I could earn based on my sales ability and I liked that. This felt much like being in business for myself.

JAY: I am confident you dodged a bullet by not following your father into retail. Both sets of my grandparents were involved in retail and, like you, my parents grew up witnessing what goes into managing a retail business and the endless number of employees and sought careers elsewhere.

I want to talk about how you successfully merged the worlds of property and casualty insurance and life insurance. Even before you joined Oswald, you tapped into a P&C firm for referrals. How did this come about and what sort of life insurance solutions did you most often place?

JEFF: Early on, I met a very successful producer who was the agent in the Guardian general agency that everyone looked up to and wanted to be. He had a beautiful suburban home, high-end cars, a country club membership, second home in Florida and a great family. He had it all!

His name was Gary, was 30 years my senior but took a liking to me and we became friends. He got me involved with the business insurance market space and helped me develop skills through joint work in the business and corporate market. Gary had great clients - dozens of privately held family businesses that always had reasons and needs to buy more insurance to protect their ever-growing risks and concerns of an expanding and growing business.

One day I asked Gary how he met so many wonderful families and businesses. He told me through a relationship he forged years ago with a very well-known P&C firm. Gary said if you can develop a relationship with a successful P&C agency, they have something we don’t, called renewals. “You see Jeffrey, P&C producers, the good ones, maintain their relationships through the renewal. They have reason to see their clients each year. However, the good ones make their clients their friends, and their friends their clients.”

Gary also told me to find a P&C firm I could work with and educate them on how I could become a profit center to their agency. I took that to heart and went on a mission to find a partnership with a P&C agency.

One of my clients at the time owned a construction company, so I asked the owner of the business who handled their P& C insurance. He gave me the agent’s name, John, and said he did all their bonding insurance and was the best in the business. I didn’t want to sound naïve, but the only bond I had ever heard of was a savings bond! Anyway, I asked my client if I could call John and use his name as a referral.

That was it! I got in the door to this very respected P&C firm and sold them on the added value and profit I could bring to their clients and agency. They gave me a shot and the rest is history. We wrote a lot of business, however, there was never any opportunity to own any part of that business and ultimately that’s what I wanted - ownership in a growing, diversified insurance agency. Oswald gave me that opportunity.

JAY: I hope established producers with younger associates in their firms show them this interview to demonstrate how relationships are meaningful to a successful life insurance career.

Many of your clients today are business owners in either family businesses or other privately held companies. Given the challenges with recruitment and retention of top talent, what are some of the trends in executive compensation you are seeing and how are your clients benefiting from using life insurance in these situations?

JEFF: We are finding many of our clients are looking for ideas to recruit and retain top talent. Our team has used deferred compensation and split dollar SERP plans very effectively for these business planning objectives. Also, many of our clients have very highly compensated employees. Rather than pay these employees 100% of their earnings through taxable bonus payout arrangements, employers are looking for ways to defer the income, and create more of an incentive for these employees to stay at the company by structuring a vesting schedule that creates golden handcuffs. This has been a very effective deferral strategy that we have positioned for many of our clients.

JAY: Since we are on the topic of recruiting, I know Oswald is always trying to find talented life insurance producers for a few of its office locations. You and I discussed how tough this has become and you have some thoughts on why this is and how we need some changes to our industry so that young people have a chance to succeed. Explain your thinking on this.

JEFF: I believe the life insurance business is one of the greatest careers a young person can choose. It provides an endless opportunity for success and, most importantly, we are helping families provide financial security for their loved ones, from sending their children to college, to being able to comfortably retire.

We help business owners transition their ownership from generation to generation, even if they can no longer work due to a disability. We help attract and retain top talent through deferred compensation plans and lastly, we help non-profits create lasting legacies for many great causes. All this is done with life insurance. What other profession can a young person go into and make such a lasting impact on families, businesses, and their communities?

The training I received in my early years is being taught by fewer and fewer organizations. The life insurance industry has dropped the ball. They have abandoned the agency system for the most part and now look to distribution outlets who provide little training and support that young up-and-coming life insurance professionals need.

It’s much easier to teach a young person to sell investments in a simple transaction and that’s where the financial services industry is going. I believe for the life insurance industry to survive, it will have to get back to recruiting, training and educating young adults on the tremendous career opportunity this industry has to offer.

We, too, have a tough time recruiting producers and often look to one of the four big mutuals for talent. They are well-trained and often are looking for an open architecture way of selling, not being captive to one insurance company’s products.

At Oswald, we have a team sales approach, and it’s not about me, it’s about what’s in the best interest of the client which leads to the best outcome for all involved. We have a culture to cross-sell our relationships across all lines of insurance and planning in which we specialize. It’s like working at a super networking group. Everyone wants to help each other and, by doing so, we all succeed. It’s a model that works and this culture is a very appealing recruiting tool.

JAY: You work a lot, but you do have a life outside of the office. Tell me about your family and what keeps you busy when you are not helping your clients.

JEFF: Jay, I guess I do work a lot, but my business is something I do because I enjoy it. It provides me satisfaction knowing that the planning we do for our clients assures them to have financial security during and post their lives.

I’ve been married to my wife, Hallie, for 26 years. We’ve raised and watched our three children grow into wonderful young adults. My oldest is 24 and is a young investment banker. My middle guy is 22, just graduated from college, and will be following his older brother into the investment banking business. My daughter, the baby, is 19 and a freshman at SMU…Go Mustangs!

We are a very close family, spending time traveling to many cool destinations. We all love skiing, golfing, the ocean, big cities, cooking and hanging out together for all the big holidays we always host. Recently, Hallie and I bought a second home in South Florida and look forward to more golf and boating.

JAY: Thanks so much for doing this, Jeff. I enjoyed it and hoped you did, too. We have arrived at the increasingly popular restaurant question. In an effort to let our industry know that there are places to eat other than steakhouses, name some non-steakhouses and non-steak dishes that our readers absolutely have to try in your neck of the woods.

JEFF: Well, like you and your readers, I do love a good steakhouse, but for the record, the best steak is the steak we at the Wasserman house prepare…we are all big carnivores!

If, and when, you and Pete decide to come to the North Shore/Cleveland area for vacation, you’ll have to come to a few of my favorites:

Dante’s is an Italian eatery run by Dante Boccuzzi, a Michelin star-rated chef. Homemade pastas and all his food is made from scratch. It is a Northern Italian menu and an excellent restaurant!

TownHall for a fun non-GMO restaurant/bar experience. Great energy!

And lastly, if you can find a member, or call me…Deep Springs Trout Club is a must. I will take you there!


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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