Getting the job done: where benefits advisors have closed deals

Our readers share the craziest places they have closed deals or made meaningful business connections.

We asked our readers, what’s the craziest or most interesting place where you’ve ever closed a sale or made a meaningful business connection?

Worth the risk

Early in my career, I sold voluntary benefits and signed up somebody at midnight using my laptop on the trunk of my car.

They were a security services company and the employee was a security guard in a crime-prone area. My laptop was the only light around. A dicey situation for sure.

Years later, that man died of a dreaded disease and I was able to help the widow file a life ­insurance claim. I would say it was worth the risk. Glad I didn’t get shot, though.

Al Schiebel, CEO & founder, Schiebel & Associates

On target

When I was on the carrier side I once recruited a couple of brokers at the shooting range. They were giving me a test and didn’t think I would show up. But I did!

Heather Garbers, vice president, voluntary benefits, HUB International

Meant to be?

I once picked up a client while at a conference regarding Postmodernism and Theology. Well, we actually had the insurance conversation at the bar after the day’s session.

Bret Brummitt, founder, Generous Benefits

Finding accord on Discord

While being approached about benefits after a yoga class has become the norm for me, spending time on Discord has become one of the most out-of-the-box radical ways to meet and connect to people. Non-fungible token (NFT) projects and brands use Discord as a gathering place for their community. NFT Discord servers are where you will find announcements, updates, and support surrounding an NFT project. People who spend time on there are actively collecting, trading, selling, and engaging in conversations about NFTs.

A year ago, while I was in a conversation about a project I collect, someone asked how I was so familiar with the health insurance and benefits industry. So I found myself sharing my career, my expertise, and my passion for lowering the cost of care and implementing meditation and yoga into U.S. health care.

We connected over Zoom, and it turned out she was a Canadian who didn’t understand the complexity and cost of health benefits even as she was building a U.S.-based entity. She was desperate to get benefits for three new hires she had made the previous month.

Read more: Making it work: How benefits professionals approach mental health

Over the last year, I have continued educating her about the ever-changing U.S. health insurance system and we have successfully built a benefits platform that supports her in attracting the best possible talent on Web3. As of today, 19 employees are working in a company that is changing the digital landscape and now have access to the best, most comprehensive, innovative health insurance benefits, while also learning how to implement Eastern medicine, meditation and wellbeing.

Naama Pozniak, founder & CEO, A+ Insurance Services

Christmas miracle

On a gondola in Telluride Colorado.

I had spent the day snowboarding with a guy that I can only describe as a typical Snowboarding Bro.  Great on the mountain and a ton of fun but I had no idea that he was the COO of 150 person financial company.  We had a fairly long gondola ride up the mountain and he asked me what I did and I explained it and a little about my personal and military background.

Him – Damn bro, you must be smart.  Do you want to work with my business.

Me – What’s your business and what do you do?

Him – I am the COO and my CFO is stuck dealing with our health insurance all the time and I can tell she hates it.  You have to be better than our current broker.

 Me – If I can help, I’d love to man.  That is the name of the game.

This CFO ended up doubling my compensation when I sent her an Invoice because I was able to cut their cost by about 25% in year one.  She is from Alabama and has the most amazing accent.  I got a call after I sent her an invoice and she said “Pat, you and your team have just done so much for us, and saved us so much money.  I just don’t feel like we are paying you enough.  Please send me a second invoice.  I am going to double the fee.”

It was like a Christmas Miracle.

Patrick Moore, president, benefit strategist, Moore Benefits Resources

Would you like fries with that?

I got a call from a prospect, walked them through what we could offer, and closed my first ever sale and my first BOR while at an old drive-in burger joint. I never thought I’d be able to close business over a greasy double cheeseburger!

Luke Davis, sales marketing manager, Texas Benefit Alliance

Playing hooky

Business professionals get stuck in the daily pressures of work and forget how to be playful. I love doing things that are fun with our clients, things they haven’t done in a while. In the middle of one work day, we had a very serious business meeting in the back of a movie theater. There is usually absolutely nobody there and it makes for a great time. It feels a bit like skipping school. I also like dragging clients to the horse race track to make a quick bet on a horse with a crazy name that relates to my client. It doesn’t have to be extravagant, just something that reminds them to be spontaneous and to enjoy life. I think my next client outing should be getting temporary henna tattoos.

Kim Eckelbarger, founder, Tropical Benefits

Related: Survey: HR leaders dealing with employee work-life balance post-pandemic

Now that’s networking

I was fortunate to insure a media brokerage company in Naples, Florida which managed a TV station in Tallahassee. Both were my clients at one time. The CFO of the company knew I had a connection to California and asked if I had my insurance license in that state. Her company acquired KADY-TV in Oxnard, California, which was formerly owned by actress Pia Zadora’s husband, who named the TV station in honor of their daughter Kady. As it turned out, they never had an insurance agent for their health plan and asked me to be their broker. Timing was perfect for everything as the TV station was insured by Blue Shield of California, which I had already been appointed with. I had a nice run with all three companies, never had the opportunity to visit the TV station in Oxnard, but KADY-TV was eventually sold to a Spanish religious broadcast company now known as KBEH.

Wayne Sakamoto, president, Health Insurance Interactive, Inc.

Rock on!

I was in northern Philadelphia at a punk rock show watching the Bouncing Souls. It was a private event with a few hundred people held at a successful brewery. In the middle of the show, I started talking with the CEO of the company and he asked what I did. I told him and he said, “We just got a 55% increase on our benefits. If you can fix that problem for us, I will give you the business tomorrow.” The next day I called him, walked him through a few scenarios and eliminated the 55% increase while keeping benefit amounts the same! Needless to say, I had a blast, got a ton of free beer and closed a deal!

Justin Leader, president & founding partner, BenefitsDNA

30,000 foot view

I met a few business executives on a Southwest flight with no assigned seats. We ended up sitting next to each other while they were flying out West for a leadership offsite and I was flying with my extended family to begin an Alaskan cruise. We talked about family and then eventually ended up discussing business, as well. About 120 days later, that organization (which had 3,000 employees) became a client and we began taking them on their journey to solve health care.

Ben Conner, president & CEO, Conner Insurance

Business casual?

While visiting family, I was in the pool and one older gentleman told me, “Hey, you need to talk to the guy over here about doing their insurance.” The deal is still in negotiation, but I have to say it’s the first time I’ve ever sold insurance in my swimsuit in the pool!

Allison Cohen De Paoli, founder, Altiqe Consulting

Swapping hats

I’ve closed a few right after compliance seminars I’ve done for clients and prospects; even one after completing an ACA Reporting update for a local NAHU chapter. Guess it’s not surprising, but always interesting how my education mode kicks sales into gear.

David C. Smith, senior VP, compliance & risk management strategies, EbenConcepts

Great expectations

The biggest deal I ever closed was during a five hour flight delay. The person sitting next to me in the terminal asked me what I thought about the book I was reading. We had a great conversation about the book that eventually turned into a conversation about business. He is the CEO of a large company and I ended up closing the deal a couple months later.

Brandon Scarborough, Executive Director of Sales and Marketing, Allied National

Follow the leader

It was a balmy day in Florida, where I was onsite at a retirement and nursing facility for open enrollment meetings. The day started normally and then it slowly became a real life rendition of Wacky Wednesday by Dr. Seuss. The facility was rather old and was eventually shut down by the state, which is indicative of where this story is going. First, the facility had recently adopted a neighborhood stray dog that they allowed to roam the halls because the residents loved him. Hoping it was an isolated incident, my hopes were quickly dashed.

The facility was two stories and the upper level is where the Alzheimer’s patients lived. I went upstairs to visit with the lovely nursing staff only to find that they were all on a break and I was now locked on the floor. As I walked around looking for any additional staff members to let me out, residents walked out of every room I passed and started to follow. Before long, I had a whole group of residents trailing behind me. One of them near the front of the crowd began screaming “He bit me” as she pointed directly at me. As I neared the end of the hall, there was only one option: lock myself in the stairwell and wait.

I eventually made my way down to the basement level and was able to get out of the stairwell after a few minutes of banging and yelling to get someone’s attention. It was a great icebreaker with the staff and led to many laughs during the ensuing enrollment meetings.

Alex Dampf, president, Oakmont Benefits Group

Couch potato?

About seven years ago, I was parked on the couch for a little over two months recovering from several surgeries due to a broken leg/dislocated knee. I actually closed several accounts from there. But after living on the couch for a few months, we decided it was best to burn it!

Derek Winn, consultant, Business Benefits Group

Planting seeds

Back at the beginning of my insurance career, I tried my hand at selling life insurance. My manager was big into estate planning cases because he said that’s where the big premiums were. He told us that farmers were great candidates for this sort of life insurance because they had a tendency to be asset rich and cash poor due to the amount of land and equipment they owned. Since I grew up in a farming community, I kind of understood that so I spent much of my prospecting time trying to contact as many farmers as I could in order to get appointments.

I remember one time when I was able to secure a late afternoon appointment with a farmer in Ropesville, Texas. He gave me very good instructions to his home and the afternoon of the appointment, I headed out for the 45-minute drive. I arrived at his house and knocked on the door, his wife answered and indicated that they were expecting me but that her husband was still out in the field. She gave me instructions and I drove another five miles or so to the location she gave me and saw him on his tractor plowing his field. When he got to the end of the turn row, he motioned for me to come up into the tractor with him. So, I grabbed my padfolio and climbed up as he proceeded to lower his plow back into the ground and keep going. After a very short introduction he said, “Well boy, show me whatcha got” as if this wasn’t unusual at all for him.

I proceeded to try to sell him a life insurance policy using several of the illustrations that I had previously prepared. After several minutes, I ran out of things to talk about, he was still plowing and it was starting to get dark. He made another few passes and parked his tractor at the end of the row next to my vehicle. He asked me to give him a ride back to his house. I obliged. When we got there, he invited me in to finish our conversation. As we entered his home, the aroma of a fresh home-cooked dinner that his wife had prepared filled the air. A part of me felt somewhat uncomfortable. First, having to give a presentation in the cab of a John Deer tractor while he was plowing, and now in his home where dinner is ready to be served. It made me think that maybe I should mention that we could schedule this for a different time when he wasn’t so busy.

Read more: 5 health insurance renewal basics to make open enrollment more successful

But before I could say anything, he gave me directions to the bathroom and instructed me to “wash up” and join him and his wife for dinner. So, I joined them for an amazing meal and some great conversation about the joys of growing up in the country and the life of a farmer. So, how much life insurance did I sell that evening? None. But even though I didn’t make the sale, it’s a great memory about an unusual experience with some very nice people.

Kelly Fristoe, president, Financial Partners

Spinning out

The VP of HR for a 900-life retail gym that ran gyms across Florida was also a spin instructor. I had been calling her for months and sending her stuff but I decided to take the spin class so I could meet her. I took the class at 5 a.m. and after the session was over, I walked up to her, barely able to breathe and with wobbly legs since it was my first ever spin class and I said, “Nice class. My name is Lester Morales.” And she said, “You’ve been sending me stuff!” So my persistence had paid off. She asked, “Did you take my class just to meet me?” And I said, “Yes, ma’am.” She told me, “Anyone who is that dedicated is someone I should be talking to. Call me today at lunch and we’ll schedule a meeting. About four months later, I wrote the account. It was a huge deal and they were my client for many years!”

Lester Morales, founder & CEO, Next Impact

Whatever it takes

I have two stories for the craziest place I closed a sale while at MZQ Consulting (I’m now with Gallagher).

My Mom had a severe stroke in the fall of 2020 (right in the middle of the strictest COVID rules the hospital had ever implemented). I worked by her bedside for 40 days—18 in ICU and another 22 on various hospital floors. The first crazy call happened when I was speaking to a potential broker partner about MZQ’s compliance services. I had our director of compliance on the call with me just in case. Mom was having what I thought was a good day and was sitting in her recliner. But halfway through our call, Mom proceeded to giddily remove her feeding tube. I calmly asked our director of compliance to please keep chatting while I put them on a brief hold and proceeded to freak out and yell for nurses. After about two minutes, I jumped back on the call. Once we were done, our director and I were convinced we didn’t get the sale—and she actually didn’t realize what had happened with Mom. A few weeks later, the broker told me the presentation was awesome and that they wanted to work with us!

Another time (and at the same hospital) there was a very important sales call I had asked our CIIO to join. He made me promise I wouldn’t take the call if I couldn’t. Two minutes before dialing in, Mom’s nurses came in for vitals. I excused myself and locked myself in the bathroom of her room to take the call. The call was excellent and we ended up winning the account! Afterwards, I came clean to our CIIO… I know it sounds crazy, but work was a welcome respite in the midst of all of the unknown.

Jen LaTour, Area Vice President, Compliance Counsel Southeast Region, Gallagher