Medicare Sales Playbook

Are you solving the right problem... or just treating the symptoms? One of the biggest reasons Medicare agents struggle isn't because of bad leads, a tough market, or not enough time—it's because they're solving the wrong problems. In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down some of the most common frustrations agents face and reveal the real issues hi...

Most Medicare agents think they need a huge marketing budget to grow their business. The truth? Some of the best marketing strategies cost little to nothing—just time, consistency, and a willingness to get uncomfortable. In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down practical, grassroots marketing ideas that any Medicare agent can start using today. From...

What do you really want—and are you willing to pay the price to get it? In this episode of the Medicare Sales Playbook, Dallas and Matt dive into one of the biggest drivers of success in business and life: desire backed by action. Too many people talk about what they want, but few stop to ask the deeper questions: Do I actually want this? Why do I want it? What am I willing to sacrifice to get it?...

What separates a record-breaking AEP from a disappointing one? Preparation. In this solo episode of Medicare Sales Playbook, Matt Smith lays out a complete 119-day roadmap to help Medicare agents prepare for the most important season of the year. From certifications and carrier contracting to referral generation, event planning, client reviews, and burnout prevention, this episode provides a month...

What happens when a successful life insurance agency decides to add Medicare to the mix? In this episode of Medicare Sales Playbook, Matt Smith sits down with Hunter Palmer of Legacy Protection Insurance to discuss how he built a thriving niche business serving truck drivers, why he shifted from traditional life insurance conversations to an "income protection" approach, and what ultimately convin...

What does it really take to build a successful Medicare business? In this episode of the Medicare Sales Playbook, Dallas Keithley and Matt Smith break down the real economics behind Medicare sales — from commissions and renewals to hiring, overrides, lead costs, and building long-term residual income. Too many agents come into the industry expecting "easy money," but the truth is that building a s...

In this episode of the Medicare Sales Playbook, Dallas and Matt break down one of the biggest mistakes Medicare agents make when quoting plans: leading with the "goodies" instead of building a true healthcare strategy. From dental and grocery cards to provider networks and prescription costs, they explain how to properly guide clients through the quoting process while building trust, increasing re...

Most Medicare agents stop at health coverage. But what if you could become the trusted advisor your clients turn to for everything related to protecting their retirement and legacy? In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with estate planning coordinator Stephanie McCann from Gold Tree Financial Group to unpack why estate planning may be one of the biggest missed...

In this episode of the Medicare Sales Playbook, Dallas and Matt dive into the advice, mindset shifts, and lessons that shaped their careers in Medicare sales. From learning to "stop talking and start listening" to understanding why clients remember how you made them feel more than the plans you sold them, this conversation is packed with practical wisdom for agents at every stage of the business....

Stop thinking like a "Medicare agent" and start thinking like a retirement specialist. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how Medicare is one of the biggest financial decisions a client will make in retirement — and how agents can use that conversation to create deeper trust, stronger relationships, and more opportunities to serve clients long-term. From ref...

If you've ever thought about leaving the corporate carrier world to go independent… this episode is your reality check—and your roadmap. In this episode of the Medicare Sales Playbook, host Matt Smith sits down with agency owner Daniel Torres to break down what REALLY happens when you make the leap from carrier rep to independent agent. Daniel shares the hard-earned lessons from building Olympus I...

What if your client meetings didn't feel like "appointments"… but instead felt like unforgettable experiences? In this episode of the Medicare Sales Playbook, Dallas and Matt break down how top agents separate themselves—not by selling harder, but by serving smarter. From creating a simple "coverage binder" to using video recaps and building relationships with the entire family, this episode is pa...

If you're waiting for referrals to "just happen"… you're leaving business on the table. In this episode of the Medicare Sales Playbook, Dallas and Matt  break down how to actually generate referrals on purpose—without sounding pushy, awkward, or salesy. Because here's the truth: 👉 Referrals don't come from luck 👉 Referrals come from VALUE You'll learn how to: Build real value that naturally driv...

If you've ever wondered why some insurance agents take off while others struggle to get traction… this episode is for you. In this episode of the Medicare Sales Playbook, Dallas and Matt break down the top 5 traits they consistently see in agents who succeed—and the habits that quietly hold others back. This isn't theory. This is what they've seen play out over years in the field. From urgency and...

What if the only thing standing between you and your next level… is the next step? In this episode of the Medicare Sales Playbook, Dallas sits down with two powerhouse leaders — Caroline Trecartin and Michael Bond — to break down what it really takes to grow in this industry. From building a family-first agency culture … to scaling from $600K to $6.3M in production … to making the leap from life i...

If you've been in the insurance business for a year or two and you're starting to ask… "Is it time to build a team?" "Should I start recruiting?" "How do I actually scale this thing?" This episode of the Medicare Sales Playbook is for you. Dallas and Matt break down the real truth about recruiting —not the hype, not the shortcuts, but what actually works (and what causes most agents to fail). Beca...

What does it really take to win in insurance sales and build an agency that lasts? In this episode of the Medicare Sales Playbook, Matt Smith sits down with Dylan King, owner of Legacy Financial Group in Phoenix, Arizona, to talk about growth, grit, sales discipline, recruiting, mentorship, and what it takes to succeed in both life insurance and Medicare. Dylan shares how he went from having no sa...

If you're a Medicare agent looking for more leads (and better partnerships) — or a Property & Casualty agent trying to protect your book during a volatile market — this episode is for you. Medicare Matt Smith sits down with Trent Sears, owner of All Services Insurance & Synergy Life and Health, to break down what happened when a successful P&C agency stopped referring Medicare out… and started bui...

Tough conversations are part of the job — whether you're setting appointments, handling objections, talking commissions with an upline, or walking a client through less-than-ideal plan options. In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to tackle hard talks without being "the conflict guy"… and without being the apologetic agent who disappears until the "32nd of...

What does it take to go from struggle… to 365 apps in a single AEP? In this powerful episode of the Medicare Sales Playbook, host Dallas Keithley sits down with Keith Laferriere of Care Connect Insurance Advisors in Bradford, New Hampshire — and this one goes way beyond production numbers. Keith breaks down: How he generated 365 apps during AEP His exact Medicare seminar system (4,000 mailers → ~8...

Dallas Keithley is back on the mic with an episode built for agents who want to level up in the middle of chaos. In this conversation, Dallas sits down with Casey Peterson and Lee Wilson from Teton Medicare (Idaho Falls and Pocatello, ID) — two former competitors who merged agencies and turned that partnership into massive momentum. They break down what happened during a wild AEP (including major...

Two years in, and we're still blown away by what this business can do—both for agents and the clients we serve. In this episode of the Medicare Sales Playbook, Matt Smith sits down with Gabe Cordova, owner of LifeMark Advisors in Mount Vernon, Missouri. Gabe shares his unexpected path from full-time ministry into Medicare, including the first client who showed him exactly why this work matters. We...

We made it — 100 episodes of the Medicare Sales Playbook 🎉 In this milestone episode, Dallas and "Mr. Medicare" Matt Smith look back on what the last 2+ years have taught them — and the one word that keeps coming up: gratitude . You'll hear: Why gratitude can change your perspective (and your business) A simple leadership principle: find people who are great at what you're not Favorite episode hi...

In this episode of the Medicare Sales Playbook, Dallas Keithley and "Medicare Matt" get real about what separates the agents who last from the agents who flame out: a servant mindset + the ability to find (and verify) answers fast. Dallas shares his mantra for the year—"How can I serve you?"—and they break down the "Can I?" part: What can I do to put myself in a better position to serve people tod...

In this episode of the Medicare Sales Playbook, Dallas and Matt unpack a simple phrase that has the power to completely transform your sales results: "How may I serve you?" In a world where every agent has access to the same Medicare contracts—Humana, UnitedHealthcare, Aetna—the real differentiator isn't the plan. It's you. This conversation dives deep into: Why clients are really "buying the agen...