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Medicare cross-selling: A win-win for clients and agents
By 
Sam Wiener
May 22, 2025
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When you don’t offer ancillaries, your beneficiaries are left exposed, and you miss out on potential revenue. With cross-selling, there’s no cost of acquisition — you don’t have to purchase more leads. These are your clients that you already have relationships with. And while selling ancillaries might seem daunting, the data is clear: the more policies you stack on top of a client, the higher the retention. 

Last week I sat down with Joanna Wyckoff, owner of Topflight Insurance, and Dustin VanDuine of Rick Young Insurance Services, to hear their thoughts on ancillaries and how they empower their agents to do more cross-selling. 

If we missed you at the webinar, watch the recording, or read through the conversation highlights below. 

Webinar Recording

Why are so many agents hesitant to cross-sell? 

When I asked Joanna and Dustin this question, they both said the same thing: fear. 

“People just don’t understand the cross-selling opportunities or how to bring it up in conversation. They think they’re going to lose the sale and get a no,” Joanna explained. 

There’s also the fear of selling beyond the $0 premium. As Dustin said, “If I ask them for a $30 premium or $50 premium, and I sold them a $0 MAPD, there’s this fear of: am I coming across as a salesman? I don’t want to be a salesperson, I just want to be an educator.”

As scary as it might seem, selling these ancillary products ultimately helps your clients. Can your client afford a $10K funeral? Do they have someone in their life who can provide them with at-home care after medical treatment? The truth is that there are a lot of gaps in Medicare coverage. 

“We want to fill as many of those gaps as possible,” Dustin said. “We’ve got to get past this fear. They deserve to be protected.” 

What are the best sales tactics for cross-selling? 

Joanna’s advice is to not go overboard — don’t start with too many products, pick just one or two that are in your market. She encourages her agents to start with Aetna Senior. “It’s in most states. You can sell life insurance, dental, hospital indemnity … you can add a spouse at the same time.” She encouraged folks to attend carrier trainings to learn how to master specific products. 

For Dustin, it’s all about the prep work and how you approach the conversation. “Gather as much information upfront. I want agents to know their client’s situation,” he said. Make sure you’re setting aside time to figure out if they have life insurance, what their assets are, if they still have an income. It’s important you’re able to look at the whole picture. 

Once you’re in the meeting, it’s helpful to have one or two questions in your back pocket that you can use to start the ancillaries conversation. When Joanna meets with clients, she talks to them about what fears they have and what sorts of struggles they’ve watched their friends and family go through.

“Don’t make a financial decision for somebody else. You don’t know their bank account or what’s important to them. Maybe they do have a history of cancer, and they would certainly love that lump sum cancer policy,” she said. “We can’t solve their problems without first understanding their true fiduciary needs.”

Dustin also stressed that you don’t have to make the sale during the first conversation. You can always have a follow-up call and say something like: “Hey last time we talked I know you were a little nervous about xyz … there’s this new product that I think is a good match for your needs.” 

Navigating these conversations is yet another example of how we’re seeing the insurance agent transition into more of a consultant role. As an agent, you can position yourself as someone who your clients go to for all of their insurance needs. You shouldn’t feel bad or pushy for offering them more options — it’s to their benefit, and at the end of the day they can always say no. 

How can you stay compliant?

The biggest takeaway from this part of our conversation was to document everything. In addition to a proper Scope of Appointment (SOA), take detailed notes, and record your calls. Joanna reminded folks to never alter any CMS-approved materials and to email all of the documents to your client after the call so you have a paper trail. 

It’s also important to clearly position these offerings as “gap coverage.” Let them know that these products are optional, they each have their own premium, and that if they decline one, it won’t impact the eligibility of the other. Avoid using language like “free” or “Medicare-approved” that could lead to confusion. 

Take the leap and start cross-selling 

The last thing I want to leave you with is the reminder that it’s never too late. You might be afraid clients will feel like they’ve been missing out if products weren’t offered to them sooner, but that’s usually not the case. As an agent, you want to avoid being in a situation where you say to yourself: “I should’ve asked them about this,” or “I should’ve told them this coverage was available.” Keep asking your clients the important questions so that you can keep them protected in the future. 

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EVP Growth @ Spark

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