Inside the Industry Health Insurance Video Podcast

Maximizing Revenue: Cross-Selling & Diversifying for Health Insurance with Emily Hollingsworth

Join Emily Hollingsworth, Operations Manager at Hilb Group Medicare, and Allison Babberl, Content Marketing Manager at AgencyBloc, for a discussion about the critical importance of diversification in the health insurance space. They explore effective methods for agents to diversify their offerings, manage their commissions, and prepare for future disruptions in the industry. The conversation emphasizes the need for education, strategic planning, and the importance of nurturing client relationships to ensure business growth and retention.

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Inside the Industry: Maximizing Revenue: Cross-Selling & Diversifying for Health Insurance with Emily Hollingsworth

Inside the Industry is a monthly video podcast hosted by AgencyBloc to take an insider's look at the health, group benefits, and senior insurance industry. Learn more about what's happening right now, what it means for your agency, and how your team can stay ahead of these changes.

Transcript for the Episode

Note: AB denotes Allison Babberl, and EH denotes Emily Hollingsworth

Allison Babberl: Welcome everyone. We have another edition of our monthly podcast, Inside the Industry. As always, I'm Allison Babberl, Content Marketing Manager here at AgencyBloc. I am joined by one of my long-time partners, Emily Hollingsworth, Operations Manager of Hilb Group Medicare. We've worked together off and on for many years now. I want to say, what, five years maybe?

Emily Hollingsworth: Yep. Five years at least, yeah, for sure.

AB: Yeah, great to have you on.You’re a long-time client of AgencyBloc, but also a long-time partner in the industry and a great advocate. You help us better understand what our clients need. So I’m really excited to have you on today.

I think today’s topic is really important, especially after such a rough Open Enrollment and Annual Election Period. Nearly everyone I’ve talked to, including you, has said it was tough. Even for people like Hilb Group. You are not a new agency. You are very well established and have been around a long time. It was still a tough season getting changes into place and navigating those changes. Regardless of whether you’re in Medicare, group, or ACA, there are changes across the board.

I’m really excited to talk to you today because you have a great session coming up at BlocBuilder 2026 about commissions processing and diversification. I want to talk about some of that today. You and I met the other day to discuss this, but I want to start with diversification. What does diversification mean to you?

EH: Diversification, especially in the Medicare space, is a hot topic right now. It’s something people really should be talking about. With the disruptions we’ve had in Medicare, especially on the commissions side, it’s important to get the most out of all your leads and referrals. Getting the most means diversifying into different products for those clients.

You can have a hospital indemnity plan along with Medicare Advantage. You can sell a cancer policy alongside Medicare Supplement or add dental coverage. There are other markets you can move into as well, like the individual ACA market. We don’t do much there, but we do a lot on the group side. That includes group Medicare, ICHRAs, and some MSAs that are great options.

I don’t advise going too wide right away. I have seen that blow up in people’s faces. Start with one thing. Dive into it. Know everything you can about those products before presenting them to clients. That includes understanding how commissions work, because they are very different from Medicare. Medicare Supplement and Medicare Advantage are different from each other. The commission schedules for hospital indemnity, dental, and group Medicare are also very different. You need to understand those implications before you start selling.

AB: I think diversification, especially in the Medicare space but even in other lines of business, is really becoming more and more of a conversation as commissions change, carrier representation changes, and plan representation changes, especially on the group side with the different types of plans. You mentioned ICHRAs and the growth in ICHRAs, along with the growth in level-funded and self-funded plans for different group sizes. There has been quite a bit of change for the industry, even for small to mid-sized groups. Knowing where your revenue streams are and how you’re future-proofing your business is really critical. From conversations I’ve had, a lot of diversification discussions focus on going into other revenue streams. I’ve heard a lot about life insurance becoming a more prominent coverage option for many insurance agents. I’ve also heard about moving into the financial side, including financial products and taxes. We all have to do our taxes every year. I don’t know about you, Emily, but I dread doing my taxes every year. I’m really bad at them. They take me a long time. I should probably just hire a tax professional at this point.

EH: I completely get it. It’s daunting even just getting the stuff together to take to the tax professional, so I totally get it.

AB: Exactly. Do I have everything? Looking at diversification, you mentioned commissions processing a little bit. I think with diversification comes a few different things. A lot of people are saying we need to do this. Looking at revenue and potential revenue for 2026, 2027, and even beyond, the likelihood that things are going to change again is very high. We don’t know what those changes are. We haven’t seen what carriers are launching this year. We haven’t seen what the commission structures are going to be. We still have a few months until that. We’re in that nice post-enrollment buffer.

But with diversification, it is definitely a must-do. What would you recommend to people on how to do it well? You said maybe choose one or two and don’t go for everything right away. It’s kind of like cake. There are a lot of great options, but maybe don’t get every piece. What other ideas do you have for navigating diversification well?

EH: Like I said, dive into one at a time. Look at each option and your book of business. A lot of people may have focused up until now 60 percent Medicare Supplement and 40 percent Medicare Advantage, or the other way around. It’s about looking at those products and seeing what pairs well with them. Where you really want to start with diversification is looking at your book of business and seeing what you can cross-sell to your current clients. There are great CRMs that can help with that. AgencyBloc is one of them. They have a great report called Cross-Sell that allows you to identify anyone who has Medicare Advantage but doesn’t have hospital indemnity, or anyone who has Medigap but doesn’t have a cancer policy. You can easily find that data and see who you can cross-sell to.

If you have mostly Medicare Advantage, you may want to start with hospital indemnity. If you have Medicare Supplement, you may want to look at cancer, dental, or life insurance. Those are all good options to pair with Medicare Supplement products because typically those clients may have higher income. Medicare Advantage clients may have lower income. Hospital indemnity pairs well with Medicare Advantage because some carriers, like GTL or Aetna, have tools where you can input the Medicare Advantage plan details and fill in the gaps like coinsurance and copays.

Start with your current clients because they trust you. It’s easier to have that cross-sell conversation. Then pivot to new clients and bring those products up in that first appointment when appropriate. Life insurance is usually better for a second appointment.

But for the hospital indemnities, your dental, you could bring that up in that first appointment. But like I said, I would start with those, original clients who know you well to start with that cross-sell. It's a little easier.

AB: I think basing it on cross-sell is one of the smartest ways to do it. As an insurance agent, you should already be cross-selling. You should already be looking at those gaps for your clients, seeing what they have with you for coverage versus what they don’t and where they may have it elsewhere. Because you and I both know retention is the name of the game, especially with the changes in new business.

With commissions changing and how much you get paid on new sales shifting, there are also changes in leads and lead acquisition. Those prices are going up just like everything else. There is inflation there. So planning how you are going to pay for new business is really critical.

Bringing it back to cross-selling, where can you build and keep the same clients you already have so you maintain that strong foundation of revenue? It always comes back to revenue, right, Emily? You know this as well as I do, especially as an Operations Manager. Every conversation comes back to revenue.

Even when you are focused on helping people and being a service partner to your clients, it still comes back to revenue. Where are your clients looking for additional coverage? Where are they saying, I wish I could have this with you? The more policies a client has with you, the higher the likelihood they are going to stick with you. If they have seven policies with you, they are probably not going to leave because that is a lot of work to find someone else who offers all of those options. Even in the group space, I know you’ve mentioned Medicare quite a bit, but ICHRAs are a whole new revenue stream for some people. It does take education, though. You cannot just dive into diversification. Education has to be at the core.

You were talking about changes in leads. Can you go into that a little more? How has lead acquisition changed in the last year, and what does that mean now as an insurance agent in 2026?

EH: For a long time, and I’ve been in the Medicare space for 16 years, when I started, we were definitely doing business reply mail. That was the core way of getting Medicare clients. I don’t want to say it was easy, but people returned those cards. It was a lot easier than it is today. Today, rarely anybody returns those cards. They are getting 10 of them a day. They are still going out, and a lot of people are still trying to use them, but they are not the old faithful they used to be. There is a lot of diversification now in lead acquisition and how brokers get their leads. Referrals are a big core of many people’s business. That can be from business partners like financial planners or group brokers, or referrals from current clients.

Those are strong ways to get clients because they are warm leads. Most of the time they are coming from someone the client already trusts, like an employer or an investment advisor. They are also generally free unless you are paying a referral fee, and even then, it can be much less per lead compared to purchased leads. So that's a great way to be diversifying your lead acquisition.

Another way is educational workshops. There are companies that help you run those. You can do community educational workshops through mailings or social media. You can also work with employers and host lunch-and-learns. That is another way to diversify your leads.

There are many different approaches now in the lead space. It is important to try different things and continue adapting because there are so many ways people are getting in front of prospects. If you are not doing that, you will fall behind.

AB: Definitely. With AI and automation growing in the last year and beyond, having tools in place to automate outreach is important. The more you nurture your clients and your leads, the higher the likelihood you will win that opportunity, especially with referrals. I talk to a lot of people who say they do not need email nurturing.

EH: They're gonna fall behind. They're definitely gonna fall behind. It's very important when you get people into your pipeline, and having a pipeline is very important. I would say if you're not using a CRM that tracks your pipeline of those leads, then you're also gonna fall behind. These are the things that I'm gonna be talking about at BlocBuilder, but it's really these things that are at the core of keeping track of your data and being ready to pivot if you need to change your lead.

Your process for your leads, of how you're going to diversify your acquisition of leads, you need to make sure that you're ready to pivot to those things. So having accurate data in your system is very important. And so using that system to reach out to those leads once you've got them.

So if you do a lunch and learn, let's say with an employer, you're going to get information about these employees. Most of the time, like we work a lot with that, we do a lot at the Hilb Group Medicare with that. And I will tell you, most of the time, you're going to have like two people out of 20 that are actually ready to retire. Most of them are not. They're just there to get some information. And then in the next two, three years, they may be retiring.

If you're not dripping on those people at least monthly, a monthly newsletter or something, then you're not top of mind. And so they may get a referral from a friend to another broker. If you're not making sure that they remember that they went to a workshop and listened to you and you had good information, you're not going to stay in their mind. They're not going to remember. So you've got to be dripping on those people to keep that. You invested time to do that lunch and learn, or to do that workshop, or whatever it was. So make sure you're also investing the time to keep and nurture those leads going forward, too.

AB: That's my new favorite phrase. You got to drip on your leads, right? Got to drip on your clients. Drip is always just a good, strong mainstay. It's been around for a long time, but it is solid. It performs, and it's something you should be doing. I think, in general, looking at diversification, kind of what I'm getting from you, Emily, is one, look at your leads or your clients. Look at your clients. What are they asking for? What are they needing? How can you start in those areas, those parallels first? That way you already know you have your core base.

Then two, make a plan for your leads. How are you getting leads? Where are you getting leads? How much are you spending on leads? Looking at your ROI, return on investment, how much are you getting from those leads? If you're paying $10 for every lead, how many of those leads are actually turning over, right? You wanna know that. That's critical, again, for revenue. And I think it comes back to what you also mentioned at the beginning. The part people probably don't think about with diversification is the commission's processing side because it changes. If you have a Medicare policy that pays at a very different rate and different timetable, different amount than a group policy would. And now ICHRAs are moving into the Medicare space even. I've heard a lot of conversation there.

So what are your recommendations, your best practices, for people going, okay, how am I gonna manage these commissions? I now have different revenue streams coming in. I might have to hire another agent. What are your best practices there?

EH: Best practice for that, the first thing you definitely want to do, if you're going to diversify and looking at commission, is first looking at those commission schedules for those new products that you're looking at doing. That's your first step, is always to make sure you understand how you're supposed to be paid. That's very important.

Not everybody does that. I deal with brokers all the time saying, how do I know how I'm supposed to be paid? Every single carrier you work with has a commission schedule somewhere. They either send it. Typically, it is part of the contract you originally signed, but every year it can change. So you always want to be looking at those commission schedules, or having someone that works for you looking at those commission schedules, analyzing how it's supposed to be paid so that you know what to expect.

One main thing is if you're diversifying away from Medicare, or adding other products to your Medicare book of business, anything that's ancillary, your hospital indemnities, your cancer policies, those pay a lot upfront, and then residuals are going to be lower. Then with group and stuff like that, that could be just a monthly rate for the whole time that they're on that policy. And it doesn't advance as we may be used to with Medicare Advantage or Medicare Supplement.

So it's looking at your commission schedules. It's understanding how those are paid, or how much those are paid, how much you're paid on those things, but also whether it's based on premium, whether it's a flat rate. And then also making sure you understand the cadence of that, of whether it's advanced, whether it's gonna be paid monthly as earned.

Because Medicare Supplement can be paid based on the premium. So can some group policies, based on premium of when the client pays. So it's understanding those things. And then you can go into your CRM and put in how you're expecting to get paid. So then you can run reports off of what you might be missing.

AB: And even some pay per life, some, as you said, flat amount. And as we said, there's a lot of people looking into that life insurance space from all different angles. There are some people looking to add Medicare to keep that continuity of coverage for their under 65 aging into Medicare. All of these different policy types pay differently.

And with changes in commission structures, changes in carrier and plan options, it is on the agent. It is your due diligence to ensure you're getting paid properly. Because if you are not, you're the only one that's going to know. Carriers don't intentionally pay you incorrectly, but it happens. Human, right?

EH: Right. It happens. Yep.

AB: And if you aren't doing your due diligence, you could be leaving money on the table, which is affecting your bottom line, your revenue, which is affecting how you can future-proof your agency, affecting how you can diversify and affecting how you can grow. And I think that's really critical. I hear a lot of clients or agents in the field say, if I'm missing commissions, it's the cost of doing business.

EH: Yeah, I don't agree with that. You definitely need to be auditing these things and also understanding that some carriers have limitations on how long you have to inquire with them on that missing commission. I believe a few of them, it's two years. Some of them, it's one year. It just depends on the carrier. So there is a limitation of how long you have to inquire on missing commissions. So that's important to understand as well.

Anything can happen. Trust me, I've seen it. I've seen all different types of things happening.

The other thing that you want to pay attention to is if they didn't get your license, or you didn't get appointed, you may not get paid. Those are things to make sure of, too. Your contracting process is important, too, to make sure you're contracted with the carrier before you sell the product so then you don't miss out on that commission. Because they may issue the policy, but they won't pay you if you were not appointed. So those are things important to catch, too, as well.

AB: And I think that's really critical for agents who work with one upline or multiple uplines, knowing where that contract is coming from, where you're contracted with that carrier. Is it through this upline, this one? Knowing all of that.

Because your upline, again, they're doing their due diligence, they're doing their best, but it does come back to the agent, to the broker. This is your livelihood. This is your business. You want to ensure you're doing the steps you need to do so that you can set yourself up for the future.

EH: We work with three or four different uplines, and we definitely do not leave it up to our upline to inform us of things because I've definitely seen that blow up in your face, too. So definitely making sure you have the information and having it in your system. You know, having a CRM to track those things because CRMs can also track your information. People think of it as just a client relationship management, but you also can use your CRM to track your licensing, your contracting, to make sure that those contracts are in place, of what states you're contracted in. Because there are carriers that do what's called just-in-time contracting. But trusting that that's just gonna happen, or trusting even sometimes what your upline is telling you, is not always correct. Not everything.

There are times I tell my staff all the time, like you'll call the carrier and you'll get an answer and you're kind of questioning it. I will definitely call the carrier back and ask again just so I can verify, because sometimes the answer you got the first time you knew was not right. So sometimes it's just re-verifying those things and asking the upline and the carrier to see if you're getting the right answer. Because sometimes you're not getting the right answer, and it can hurt your bottom line.

Like you said, it is ultimately up to us as the brokers to know that we are appointed, we're certified, and that we are getting paid the right amounts. It is ultimately up to us because we are business owners. When you are a broker, my mom's a broker too, my husband's a broker, so I see this all the time and I harp this at my mother, too, all the time. But basically, you are a business owner. You need to look at it as you are in charge of all of this. This is all up to you to make sure that all of this is buttoned up and you are checking these things continually because it can add up really fast if you put it off.

It can add up really fast, and then you're going back two years auditing your records. So it's definitely checking these things continually is what's gonna help you make sure that your bottom line is straightened out.

AB: Trying to audit two years past when you're also trying to grow, that's just a lot to take on. And tying it back to diversification, again, knowing that you are prepared and ready to take on those new lanes, making sure you are certified with the proper carriers, right? If you only sell one line of business now and you want to diversify into another, you can't just start selling their insurance policies because you want to. You have to make sure it's in your state. You have to make sure you have the proper certifications. You have to make sure your licenses are up to date, all of that. That is critical. All of this wraps back into if you want to diversify, which many have to right now to keep their business going and growing, then these are the steps you need to take.

EH: Finding the right upline that will support you, because there is support out there from the right upline. And finding the right upline that will help support you in that diversification because a lot of them do have education. Right now, with our company, we have what we call coaching calls. And we will have representatives from different carriers come on to that coaching call to talk about those hospital indemnities, those cancer policies, those other policies that we can sell because so many of us were so focused on Medicare for so long that the diversification right now can be daunting. Getting that education is so important, and those carrier reps can definitely help with that. So your uplines, a lot of times, will have those trainings on those products, and you can learn more about the products. They can also provide you with those commission schedules like we talked about so that you can educate yourself on the products and how you will be paid so you can be ready when you're ready to diversify.

AB: Yes, 100% agree with all that. I work with uplines from across the country, and I always learn so much from them. Not being an agent myself, but just being in the industry, I learn so much that is critical for me to help provide the education AgencyBloc puts out to ensure that agents across the country are taking the best steps to manage their business.

EH: 100%.

AB: Amazing. Thank you so much, Emily. I think this is a really critical topic. It's a really current topic for a lot of people, especially coming out of 2025 and all of the changes and that really rough season. As we prepare for another Open Enrollment and AEP coming up, what does that look like? Especially with the enrollment peak for group coming up this summer. What does that look like? How do we prepare? And how do you best set your agency up for success?

EH: We definitely had, like I said, a bumpy 2025. Our 2026 AEP, we were not prepared even, and I've been doing this for 16 years. But it was, there was a lot of disruption, different kinds of disruption. I think that's what we weren't ready for last year. It was carrier disruption, it was legislation disruption, it was commission disruption. Everything that could happen all happened during one AEP. So what we did is we pivoted quickly. And that's one thing I will say about our team. We pivoted quickly, and we figured out ways to fill the gaps and figure out what we could do. So getting prepared for 2027 AEP, we definitely had what I called a debrief session where we talked about everything that went wrong. You have to be ready to have those conversations and just talk about where we were lacking. And it's hard. It's hard to even think about where was I lacking? Where could I have done better? These are things you have to think about. These are things you need to document. So then during 2027 AEP, we can be ready for those things.

And we also need to think about, like we've talked about, where we could diversify because we don't know what's gonna happen for 2027 AEP. We don't know what more commission disruption, heaven forbid, we have. What more product disruption we could have. What more legislation we could have. We don't know what's gonna happen for 2027 AEP. So we do need to be prepared for what anything could happen. So it's important to be ready to pivot and not be so rigid in how we think about AEP and be ready to do those things that we need to do. But also looking back to last AEP to figure out where were the gaps that we can fill in for this AEP.

AB: Yeah, and I think that's critical. If you are a single agent, small agency with a couple agents, growing, large, even up into an IMO, FMO, uplines, everyone in between, regardless if you sell just one product or you've already started diversifying, looking back to then look forward. Change will come. We don't know what that change will be. It probably isn't going to get instantly better and back to normal, right? That's probably off the table at this point. So where can you set yourself up so that you can adjust and maneuver when those disruptions come and you can feel prepared.

Thank you so much, Emily. This is such a great topic, great information. We'll probably discuss more at BlocBuilder and, you know, as we share this out, I'm sure many people are going to be commenting and saying, yes, I have this experience. This is what I've been seeing. So a lot yet to come in 2026. Right now it is February. Let's see what happens.

EH: Yeah, absolutely. Can't wait to see.

AB: Thank you everyone. We'll see you here again next month for another edition of Inside the Industry. Thanks again to our guest today, Emily Hollingsworth, Operations Manager of Hilb Group Medicare. It's been great.

EH: Great. Thanks, Allison. This was wonderful.

Posted on Thursday, February 26, 2026 in Inside the Industry