Insurance telesales tips from an agent who started at zero

Brian Holden didn’t make a single sale in his first two and a half weeks of health insurance. His manager still tells people Brian was his worst salesman. Three and a half years later he’s a regional leader at USA Benefits Group, and his renewals let him take a whole summer off.

When we sat down again, I asked for his best insurance telesales tips. Almost none of them are about products. They’re about numbers, tone, and honesty.

Watch the full interview with Brian on YouTube.

Insurance telesales runs on renewals, not heroics

The reason Brian could take the summer off is renewals. A lot of agents assume private health pays worse than life. His experience is the opposite: an upfront commission plus renewals that keep hitting every month, and on some plans, commissions paid as earned with no chargebacks.

That changes how you sell. You stop sounding desperate on the phone. Brian put it simply: when you don’t have to fight to pay the bills, you can focus on the stuff that makes you you.

His rough math for new agents: write 20 family plans between September and the end of open enrollment and the renewals add up to real annual income. He’s set his own open enrollment goal at 200. (That’s his comp and his carriers. Yours depends on your contracts, so run your own numbers before you plan around his.)

He also plays the seasons. Summer is slow because people feel fine. Winter brings open enrollment, cold weather, and people thinking about their health. About a third of his business lands in open enrollment.

Bad leads and the 10% rule

Every agent has complained about leads. Brian’s answer: “All leads suck and all leads are great.”

If he closes 10 to 12% of his leads, he’s doing well. That sounds low. It doesn’t have to be high. Close 10% of 50 leads a week and that’s five sales. By his math, three a week puts an agent on a six-figure track. (That’s his experience with his leads and contracts, not a promise. Your results depend on your own.)

Look at it the other way and nine out of 10 leads “failed.” Bad number, no answer, didn’t qualify. Statistically the leads are terrible. That’s not the point. You’re looking for the one.

He also doesn’t let the other nine die. At the end of the year he texts everyone who never resolved (only the ones who gave consent, more on that below), and a chunk of them come back interested. It’s a second shot at leads he already paid for.

Track 100 dials so you know where you’re losing

When Brian was building, he used a sheet of 100 little squares. He’d call 25 leads, take a break, come back, call 25 more. He has a short attention span and he’s honest about it.

At the end of the day those 100 dials told him exactly where he stood:

• How many picked up
• How many became real conversations
• How many fact-finders and pitches
• How many closed, and how many no-showed

That breakdown is what makes coaching possible. If nobody gets past the intro call, the intro is the problem. If they get through the intro but ghost the pitch call, the discovery conversation is the problem. Without the numbers, all you’ve got is your feelings, and your feelings will lie to you.

The first five seconds decide the call

Private health is a two-call process for Brian, sometimes three. Call one is not about products. It’s about you.

“If I called you and said ‘Mr. Holm,’ immediately you’d know I’m trying to sell you something,” he told me. So he opens like a normal person: “Hey Sean, how’s it going? This is Brian. You filled out my health form a few minutes ago. Can I borrow you for a minute?”

That one line covers the four things every call needs: who they are, who you are, why you’re calling, and what happens next. Then he slows down. He tells people he’s in North Georgia, five minutes south of Chattanooga. Nobody cares, and that’s fine. It helps them picture a real person.

He doesn’t use scripts. He has key points and he adjusts. A retiree in New York gets a different tone than a trucker in Nebraska. The Northeast wants it done fast. The Midwest wants to talk about the deer in the backyard. You only learn that with reps, and by recording and replaying your own calls. He still cringes at his.

Tell them what’s wrong with the plan

This is the part most agents won’t do. Brian explains why a plan is good and why it isn’t. “I know health insurance sucks. I’m not trying to tell you this is great.”

His line on commission: “Yes, I’m commission based, but I don’t get paid if you buy it. I get paid if you keep it.” He built his business on retention and referrals, and he can’t get either by putting someone in a bad spot.

It works because clients can hear that he means it. When he explains how a fixed-benefit plan and a catastrophic plan fit together, and where the gaps are, clients stop bracing for a pitch. The week we talked, every sale he’d made came from referrals.

Let AI handle the busywork, keep the call human

Brian figures 80% of the business is stuff he doesn’t want to do. His CRM and AI tools take most of it: texting, reminders, and a post-sale email series triggered by the plan he sold. That frees him to spend more time on the 20% that pays, which is talking to people.

He doesn’t want the AI doing the talking. People are dealing with medical history and real fear on these calls. They want a normal person.

Before you copy any of this, check the rules:

• Outbound. Automated texts, calls, and mass follow-ups to old leads need proper consent under the TCPA and state rules (consent that names you, not just the lead vendor), a Do Not Call scrub, state quiet hours, and an easy opt-out. That goes double for texting leads who are months old. Carrier and state marketing rules apply to what the messages say.
• Recording. Recording your calls to review them is great practice, but some states require every party to consent, including Florida, California, Pennsylvania, Washington, Illinois, and Maryland. Get consent at the start of the call, before you record.
• Client data. Health details and applications are regulated no matter which tool touches them. Use business-tier AI accounts that don’t train on your data, and check your carrier agreements before uploading anything.

A tool can draft the follow-up. You’re still responsible for what goes out.

Run the ball

Brian has a hat in his office that tells him to run the ball. You’re going to get hit in the mouth. The better you get at slipping those hits, the further down the field you get. Track your numbers, sound like a person, tell the truth about the plan, and let software carry the admin.

If you want a CRM that already has the texting, follow-up, and post-sale workflows built for insurance agents, take a look at NextLevel CRM.