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Transform Your Group Health Benefits Strategy | Dan Pascone with Mark Karlie | Podcast #10

TL;DR

Many employers treat the group health insurance renewal as something that happens to them, but Mark Karlie says there are other ways to finance coverage, and the starting point is getting your data. In this episode, Mark, president and partner at 28 Insurance, explains why transparency and a willingness to think outside the box matter more than another round of the same status quo.

Mark has spent a little over 25 years in group health insurance, working with employers that have roughly 50 to 750 enrolled employees. We cover who inside a company gets involved (CFOs, CEOs and HR directors), why so many employers stay stuck, where he expects the industry to go over the next 5–10 years, and a lightning round that shows what drives him outside of work. Mark's views are his own, and this is general education, not insurance or benefits advice.

Who Is Mark Karlie?

Mark Karlie is the president and partner at 28 Insurance, a firm that specializes in group health benefits. He's been in the business for a little over 25 years. Like a lot of people in this field, he didn't plan on it. He told us he got tired of the grind on the financial side of his earlier career and made a change about 25 years ago.

His firm works with employers whose groups run from about 50 to 750 enrolled employees. When we asked what makes his firm different, his answer was thinking outside the box.

Who 28 Insurance Works With

Mark doesn't target a specific industry. He told us it's about the size and scale of the employer, with 50 to 750 enrolled employees as the target range.

The people he talks to most are CFOs, CEOs and HR directors. The CFO is involved because the conversation is about how the company finances its healthcare. The HR director gets looped in as well. Health coverage is only 1 piece of the employer benefits picture. Retirement plans are another, and we break those down in Company Retirement Plans: The Ultimate Guide.

Changing How Healthcare Is Financed

Mark's primary strategy is helping employers change how they finance their healthcare, using what he called a benefits cap. He said this approach is saving clients a ton of money and changing how they're able to deliver coverage.

We'll leave the mechanics to licensed benefits specialists, since the right structure depends on a company's size, claims history and risk tolerance. What we took from the conversation is the mindset: how you pay for coverage is a decision, not a given.

Why Employers Get Stuck in the Status Quo

When we asked about the biggest challenge his clients face, Mark said many of them don't know there are other strategies available in the group health insurance market. They're stuck in the status quo, and they're looking for someone who is transparent and thinks outside the box.

His approach is to come to them with that transparency and show them how things work, rather than leaving them with a number and a few familiar options.

Control Starts With Data

We asked Mark what it means to give a business leader control. His answer was direct: giving control is getting the data right and knowing what's going on within your group plan.

That lines up with how we think about money. It's hard to make good decisions about what you can't see. We make a similar argument for personal finances in Reduce Financial Stress with a Control-First Playbook.

How Mark Finds Clients and Partners

Mark attracts clients through on-site seminars and education. For referrals, he works with CPA firms and attorney firms who bring him clients curious about different strategies.

A good referral partner, in his words, has the same mindset: it's about educating the person, not trying to sell them. That's close to how we run our own podcast and content, so it was a natural conversation.

Where He Sees the Industry Going

Over the next 5–10 years, Mark expects a lot more transparency, because there has to be and it isn't there now. He also expects the market to be more results driven, because the rate increases employers are getting aren't sustainable. In his view, that will push brokers to think outside the box and bring fresh ideas to their clients.

To stay ahead of that, his team engages clients on new ideas, stays curious and stays transparent. For broader context on how employer coverage costs trend, KFF publishes an annual Employer Health Benefits Survey.

Lightning Round Highlights

  • Coffee or tea, cats or dogs: Coffee and dogs.
  • Tech he can't live without: His earbuds, mostly for podcasts and a music app.
  • Favorite quote: “Life is happening for you, not to you.”
  • Favorite book: Dalio's book on principles.
  • Personal hack: 10–15 minutes to himself every morning, with gratitude and no phone. He's a spiritual person, so for him that includes prayer.
  • Bucket list item already checked off: Becoming a business owner.
  • Financial milestone he's working toward: $28 million in revenue by year 15.
  • Why 28: The company name comes from Deuteronomy 28.

What Most People Miss

For many employers, group health shows up as an annual rate increase, a few familiar options and a quick decision. What Mark points to is that the financing structure itself is a choice, and that you can't evaluate that choice without data on what's going on inside your plan.

The takeaway isn't that any 1 funding approach is better. It's that the conversation tends to start with too little information. Asking for your data and a clear explanation of what's behind your costs puts you in a position to ask better questions, whatever you decide.

Example (Hypothetical): What Rising Health Costs Could Do Over 3 Years

Assume a company has 200 enrolled employees and spends $2,000,000 a year on group health, or $10,000 per enrolled employee.

  • If costs rise 10% a year for 3 years: annual spend reaches $2,662,000, which is $662,000 higher than today.
  • If costs rise 5% a year for 3 years: annual spend reaches $2,315,250.
  • The gap between the 2 paths: $346,750 a year by year 3.

That's money that can't go to hiring, reinvestment or owner distributions. These are assumed figures meant to show how compounding works. They aren't predictions, and they aren't a claim about what any funding strategy would do. Actual results depend on claims, plan design and risk.

How This Fits Our Approach at Tailored Wealth

We're not a benefits broker, and we don't evaluate or recommend group health strategies. But employer benefits show up in our work in a few places. We use Life-Driven Planning, our 6-phase process (Cash Flow, Retirement & Hybrid Retirement, Risk, Expense & Goal, Tax and Legacy), to look at the whole picture. Hybrid Retirement is a phased approach where full-time work gives way to flexible, optional work rather than an abrupt stop.

For a business owner or CFO, the cost of employer health coverage shows up in cash flow and risk. For an executive, your own benefits elections feed your expense and tax planning. Mark's point about getting data mirrors how we start any plan: see what's really there first. To see what a plan covers end to end, watch What a Real Financial Plan Includes.

Who This Is For

This episode is for CFOs, CEOs, business owners and senior leaders at companies with roughly 50 to 750 enrolled employees who are tired of treating the group health renewal as a cost they can't influence. It's also for executives in their 40s and 50s with complex compensation who want company benefits, taxes and their retirement timeline to work together.

Frequently Asked Questions

What size companies should consider alternative funding for group health?

Typically, employers with 50 or more enrolled employees can begin exploring options beyond fully insured plans, such as benefits caps, level funding, or partially self-funded arrangements, especially if they’re facing steep renewal increases year after year.

Why is transparency such a big deal in group health?

Without claims and utilization data, employers can’t see what’s actually driving their costs, which makes it almost impossible to manage them. Transparency allows better plan design, vendor negotiation, and more strategic decisions.

Who inside a company should lead a group health strategy reset?

Usually it’s a partnership between the CFO (for financial and funding decisions), the HR director (for employee experience and administration), and the CEO or owner (for overall direction and risk tolerance).

How do I know if my company is “stuck in the status quo” on benefits?

If your annual renewal conversation is basically: “Here’s your increase, here are a few carrier options, maybe tweak deductibles,” with no deeper data discussion or creative strategy, you’re likely in a status quo pattern.

What’s one simple step to start improving our benefits strategy?

Begin by asking for your data and a detailed explanation of what’s driving your health spend. Then have an education-focused conversation with a benefits advisor who is willing to walk you through alternative funding options and their pros/cons.

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What did Mark mean by a “benefits cap”?

Mark described a benefits cap as the primary strategy his firm uses to help employers change how they finance their healthcare, and he said it's saving clients a ton of money. He didn't walk through the mechanics on the episode, so the details are worth taking up with a licensed benefits professional who can look at your company's size, claims and risk tolerance. This is general education, not a recommendation.

What should a CFO or business owner know before changing a group health strategy?

Treat it as a financing decision, not just a benefits decision. It touches cash flow, risk and how your people experience their coverage, which is why Mark talks with CFOs, CEOs and HR directors together. His starting point is data: know what's going on within your group plan before you decide anything. Bring in the professionals you already trust, such as your CPA, attorney and a licensed benefits specialist.

I'm an executive thinking about easing out of full-time work. Where does health coverage fit?

Health coverage is one of the variables to plan for. Employer coverage often ends or changes when you leave, and Medicare eligibility starts at 65, so the years in between need a line in your cash flow plan. A Hybrid Retirement, where full-time work gives way to flexible, optional work rather than an abrupt stop, can change how long that gap runs. We walk through it in Retire Gradually, Not All at Once (Hybrid Plan Guide). If you'd like to see how your benefits, taxes and timeline fit together, you can book a Free Wealth Strategy Call.

Talk Through Your Own Plan

If you're a business leader or executive and want to see how your company benefits, cash flow, taxes and retirement timeline fit together, we're happy to talk it through. It's a low-pressure conversation about your situation. Book a Free Wealth Strategy Call.

Disclosure

The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon.

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