Marty Levy

A few years ago, if someone told you that artificial intelligence would be helping people interpret lab work, prepare for doctor visits, and even guide them toward treatment options, it would have sounded like science fiction. Today, it’s quietly becoming part of everyday healthcare.

With OpenAI’s recent move into healthcare through what’s now being called ChatGPT Health, the question isn’t whether AI will influence medicine — it already is. The more interesting question is how far it goes, and what role it plays alongside real physicians.

What’s Actually Changing

Healthcare has always struggled with one major problem: information overload with very little clarity. Patients receive test results, notes, portals, summaries, and instructions — often without context or explanation. Most people leave doctor visits remembering only a fraction of what was discussed.

AI tools like ChatGPT are stepping into that gap.

The idea behind ChatGPT Health isn’t to diagnose or replace doctors. It’s to help people make sense of their health information — lab trends, medication questions, symptoms, and even what questions they should be asking next. Think of it less as a doctor and more as a highly organized, always-available health translator.

That distinction matters.

Why This Feels Different Than “Dr. Google”

We’ve all Googled symptoms. That usually leads to anxiety, confusion, or worst-case scenarios. AI is different because it can be contextual. It remembers what you’ve shared, recognizes patterns, and frames information in plain language — not alarmist headlines.

For many people, this becomes a way to prepare for a visit rather than replace one. Better questions. Better understanding. Better engagement.

And that alone is a meaningful shift.

Telehealth Has Already Normalized This Behavior

At the same time AI is evolving, telehealth has quietly changed how people access care.

Companies like Amazon One Medical now offer on-demand virtual visits for common conditions — including things like UTIs, sinus infections, pink eye, anxiety, and routine prescription needs. You describe symptoms, interact with a licensed clinician, and in many cases a prescription is sent directly to a pharmacy without stepping into an office.

For straightforward, episodic issues, this model works — and consumers have embraced it.

What’s important is recognizing the direction of travel:
People are already comfortable getting healthcare guidance digitally.

AI simply becomes the front door — helping people decide when they need care, what kind of care they need, and how urgent the situation actually is.

So… Is ChatGPT Your Next Internist?

Not exactly — and that’s the wrong way to frame it.

AI isn’t replacing internists any time soon. It doesn’t examine you. It doesn’t order imaging. It doesn’t make judgment calls in complex or ambiguous cases. And it shouldn’t.

What it does do is something medicine has struggled with for decades:
give people time, clarity, and continuity.

• Time to think through symptoms
• Clarity around confusing medical language
• Continuity between visits, test results, and lifestyle data

That makes patients better informed — and frankly, better partners in their own care.

The More Likely Future

The future of healthcare isn’t AI versus doctors. It’s AI supporting both patients and clinicians.

• Patients show up better prepared
• Physicians spend less time explaining basics and more time treating
• Telehealth handles routine care efficiently
• In-person medicine focuses on what truly requires human judgment

In that model, AI doesn’t replace the internist — it acts more like a clinical assistant, educator, and guide that never gets tired.

And for a system under pressure from cost, access issues, and burnout, that may be exactly what healthcare needs.

The real takeaway isn’t whether ChatGPT becomes your doctor.
It’s that healthcare is finally starting to meet people where they already are — informed, digital, and looking for clarity.

For decades, COBRA compliance has been one of those “necessary evils” for employers — a regulatory requirement buried in HR checklists and legal manuals. Under federal law, employers offering group health plans must allow eligible former employees and their families the option to continue coverage when employment ends or hours are reduced. Employers must notify departing workers and ensure the paperwork is handled correctly — or face compliance risk.

But once that obligation is met, the experience has traditionally ended abruptly.

A health plan continuation notice. A severance package. Laptop access terminated. Key cards turned in. And then — goodbye.

For many employees, especially those who have spent years or even decades with an organization, this moment feels less like a transition and more like being cut loose. After long careers of contribution and loyalty, they are suddenly left to navigate healthcare, income uncertainty, and job transition entirely on their own.

The Human Side of Off-Boarding Has Long Been Ignored

Historically, COBRA administration has been treated as a purely transactional exercise. Employers — even thoughtful, well-intentioned ones — have focused on compliance while overlooking the emotional and practical complexity of what happens next.

Yet the COBRA election window often coincides with one of the most stressful periods in a person’s life:

• Confusion around deadlines and eligibility
• Sticker shock when premiums shift from employer-subsidized to employee-paid
• Lack of clarity around alternatives like the individual market, Medicare, or Medicaid
• No support for related coverage decisions such as dental, vision, or life insurance

Compliance may have been satisfied, but support was not.

A New Model Emerges: COBRA Compliance Meets Employee Assistance

That dynamic is starting to change.

A new category of solutions is emerging that reframes off-boarding as more than an administrative ending. Companies like Kept.io are helping redefine what COBRA support can look like by combining compliance with education, guidance, and practical transition support — something that closely resembles an Employee Assistance Program for departing employees.

Instead of simply handing someone a COBRA notice, this approach provides:

• Clear, understandable guidance around COBRA mechanics and timelines
• Support in evaluating alternatives such as exchange plans, subsidies, Medicare, or Medicaid
• Help identifying gaps in coverage, including dental, vision, and life insurance
• Resources that extend beyond insurance, including job placement and transition support

This creates a bridge — not just between employment and healthcare coverage, but between one chapter of a career and the next.

Why This Matters to Employers

The way an organization treats employees at the moment they leave often leaves a deeper impression than how they were treated while they stayed.

A more thoughtful off-boarding experience:

• Preserves dignity during a vulnerable moment
• Reduces confusion and poor decision-making around healthcare
• Strengthens employer brand and long-term reputation
• Aligns compliance obligations with cultural values

Former employees don’t vanish. They become future hires, referral sources, customers, and ambassadors — or detractors. How they experience their exit matters.

CorpStrat’s Perspective

At CorpStrat, we spend every day working with employers on benefits strategy, risk management, and workforce planning. We also see firsthand where systems fall short — particularly at moments of transition.

That’s why CorpStrat principals have chosen to invest in Kept.io

Not simply as a vendor relationship, but because we believe in the concept: that terminated employees deserve more than a packet and a deadline. We believe COBRA electees should be supported, educated, and treated as consumers navigating complex decisions — not as administrative loose ends.

We also hope insurance carriers and the broader benefits ecosystem continue to move in this direction, embracing more consumer-centric thinking around COBRA elections and post-employment coverage.

Looking Ahead

COBRA was designed as a safety net — not a roadmap. But today’s workforce demands more clarity, more support, and more humanity at moments of change.

Startups like Kept.io represent an important cultural shift — one that moves off-boarding from cold compliance to thoughtful transition. While the path of any startup may evolve, the direction here matters.

The future of employee benefits will be shaped not only by how companies care for people while they are employed — but by how they help them move forward when they are not.

If you want to understand where healthcare in America is headed, start with this simple truth: health insurance has become a political hot button not because insurers suddenly changed, but because costs continue to rise faster than wages, inflation, and expectations. Over the past year, this tension came to a head when Congress effectively shut down for months over a single issue—whether to extend the enhanced Affordable Care Act (ACA) premium tax credits that were introduced during COVID.

Those subsidies made coverage meaningfully more affordable for millions of Americans. When they expired, outrage followed.

The debate wasn’t just about dollars. It was about equity, affordability, and who ultimately bears responsibility for a system that feels increasingly fragile.

The ACA Subsidy Cliff: A Manufactured Crisis

Beginning January 1, 2026, millions of Americans face what policymakers call the ACA subsidy cliff. Temporary enhanced subsidies disappear, and for many households—particularly older individuals and families earning just above traditional subsidy thresholds—premiums could double or even triple overnight.

For some higher-income households over age 50, annual premiums could jump from under $10,000 to more than $30,000 per year. That isn’t a market correction—it’s a shockwave.

Lawmakers on both sides acknowledge this problem. What they don’t agree on is how to fix it, or whether extending subsidies indefinitely is fiscally or structurally sound.

Congress Weighs a New Direction

In December, House Republicans rolled out the Lower Health Care Premiums for All Americans Act, a sweeping package that includes:

• Expanded access to Association Health Plans (AHPs)
• Major reforms and transparency requirements for Pharmacy Benefit Managers (PBMs)
• Limits on states’ ability to regulate stop-loss insurance for self-funded plans
• A reboot of Individual Coverage HRAs (ICHRAs)—renamed under the proposed CHOICE Arrangement Act

Notably, the bill does not extend enhanced ACA premium subsidies, though it does fund the ACA’s cost-sharing reduction program starting in 2027.

Translation: Congress may act on healthcare this year—but not necessarily in a way that stabilizes the ACA marketplaces.

The Uncomfortable Truth: Insurance Companies Aren’t the Villain

Public discourse often paints insurers as the problem. But insurers have always been what they are today: risk managers and administrators, operating within the costs imposed on them.

The real cost drivers are elsewhere:

• Explosive growth in healthcare technology
• Astronomical pharmaceutical pricing
• Consolidation among hospital systems
• A lack of meaningful price transparency

Insurance companies didn’t create these dynamics—they react to them.

Vilifying insurers may be politically convenient, but it does nothing to address the structural forces driving premiums higher year after year.

Market “Solutions” With Real Tradeoffs

Association Health Plans and expanded ICHRAs sound appealing—and for some employers, they may be. But there’s a downside that policymakers rarely discuss:

They siphon healthier groups out of the ACA risk pool.

When younger, healthier populations exit the ACA marketplaces, the remaining pool becomes older and sicker—driving premiums even higher for those who depend on ACA coverage the most.

That’s not reform. That’s fragmentation.

Ironically, many of the “solutions” being proposed to reduce costs may undermine the very stability of the ACA, accelerating the problem they aim to solve.

Is the Government Going to Fix This? Probably Not.

History suggests the federal government is unlikely to step in as a long-term insurer or price controller. Healthcare will remain a market-based system, even as regulation ebbs and flows.

That means:

• Employers will continue to explore alternative funding models
• Individuals will face more responsibility—and complexity—in coverage decisions
• Innovation will come from market forces, not sweeping federal overhauls

What Comes Next

Healthcare in America is at an inflection point. Premium subsidies, association plans, ICHRAs, PBM reform—all of these matter. But none of them are silver bullets.

The real solution will require:

• Honest conversations about cost drivers
• Smarter risk pooling—not weaker
• Market-based innovation with guardrails, not political theater

Until then, volatility—not stability—will remain the norm.

And for employers, individuals, and families, navigating this environment will require clarity, strategy, and proactive planning more than ever before.

After decades in the insurance and advisory world helping business owners, families, executives, and high net worth individuals navigate decisions they never expected to face, one truth stands out above everything else.

The smartest and most successful people I have met all embrace two things.
They value planning.
And they value planning for the unexpected.

And this is not a pitch to buy insurance. It is the opposite.

I have seen people purchase too little coverage and I have seen people purchase far too much. I have designed every type of plan you can imagine. But after watching thousands of real world outcomes, one thing is certain.

Success leaves clues.

The top performers in every field understand one simple principle.
Leverage plus risk transfer equals freedom.

They do not rely only on their own balance sheet.
They do not pretend that they will never get sick, disabled, sued, or caught off guard.
They use planning tools, including insurance, to protect what they have built and to create options for the future.

But for the average person, interacting with insurance companies is challenging.
They move slowly. They are rule driven. They are never proactive. And if you are not careful, the smallest mistake can cost you dearly.

After a lifetime in this industry, these are the four biggest mistakes people make with insurance and long term planning.

1. The “Set It and Forget It” Approach Is the Most Dangerous Strategy

Many people buy insurance and never look at it again.

But the world changes. Health changes. Costs change. Products evolve. Some policies lose value. Some become obsolete. Some explode in cost later in life. Some were designed incorrectly from the very beginning.

Every insurance product should be reviewed once a year.
Not every five years. Not “when I get to it.”

A one hour review would have saved many people years of financial stress.

2. Incorrect Ownership and Beneficiary Designations

This is one of the most common and damaging mistakes.

Insurance always pays the person listed on the form, not the person you intended.

Divorces. Remarriages. Estranged family. Business partners. All of these create landmines.

I have seen:

• Former spouses receive multi million payouts
• Children accidentally disinherited
• Unnecessary estate tax exposure because of incorrect ownership
• Qualified plans left to the wrong people
• Policies pulled into a taxable estate due to bad structure

And once the insured passes away, the form controls everything.
This is the easiest mistake to fix and the hardest one to correct later.

3. Policy Owners Who Never Request Annual Ledgers

This has created more “oh no” moments than anything else in my career.

Most people who own whole life, universal life, or indexed universal life have never:

• Requested an in force ledger
• Checked crediting rates
• Reviewed internal charges
• Stress tested how long the policy will last

Then one day they receive a letter that says:

“Your policy needs additional premium to stay active.”

This usually happens when they are older.
Usually when they are on fixed income.
Usually when the cost is significant.

A simple annual review prevents these surprises.

4. Forgetting That Insurance Is a Buyer Beware Category

Insurance companies will not remind you about:

• Better options
• Declining performance
• New features
• Updated riders
• More efficient strategies

They do not call. They do not email. They do not offer courtesy reviews.

This lack of proactive service has caused many lawsuits over the years.
Time and neglect is a dangerous combination.
This is why stewardship matters.
This is why an advisor matters.

My Recommendation: Hold an Annual Planning Summit

Once a year, gather your advisors.

Your insurance professionals
Your estate planner
Your accountant
Your business attorney
Your financial advisor

Review the following.

Your goals
Your exposures
Your balance sheet
Your beneficiary designations
Your insurance portfolio
Your business risk
Your tax posture
Your estate planning documents

Make sure everything aligns.

If your advisors avoid reviewing what you already own, you are working with the wrong people.

Planning is not a one time event.
It is a living and evolving process.
It is the foundation of financial confidence.

The most successful people I have ever met understand this.
And you should too.

Marty Levy, Founder, CorpStrat

For years, HSAs were limited to only a narrow set of “HSA-eligible” high-deductible plans. That left many people on Bronze plans or Catastrophic plans unable to take advantage of the tremendous tax benefits HSAs provide.

Starting in 2026, the rules change — and for the better.
With the passage of the recent OBBB, you can now fund an H S A when insure dunder most Bronze and Catastrophic plans. This creates a powerful planning opportunity for individuals, families, and employers.

Why This Matters

If you can pair your medical plan with an HSA, you unlock three big tax advantages:

• Pre-tax contributions
• Tax-free growth
• Tax-free withdrawals for qualified medical expenses

Plus:

• Unused balances roll over every year
• You can invest the money
• HSAs effectively become another retirement-planning vehicle

And now that many Bronze and Catastrophic plans qualify, far more people have access to an HSA

Whats an H S A and Why Does it Make Sense

Straight from the official source:

• Insurance plans labeled “Eligible for an HSA” will include Bronze and Catastrophic options beginning in 2026.
• Any plan paired with an HSA must still meet the IRS definition of a High-Deductible Health Plan (HDHP).
• Once you enroll in an HSA-eligible plan, you can open an HSA at a bank, credit union, or any institution that offers them.
• You can use your HSA dollars for:
  • Deductibles
  • Coinsurance
  • Copays
  • Dental & vision expenses
  • And over-the-counter items

Source: HealthCare.gov – HSA Options
https://www.healthcare.gov/hsa-options/

2026 HSA Contribution Limits

Here are the newly adjusted IRS limits for 2026:

• $4,400 — Individual coverage
• $8,750 — Family coverage
• +$1,000 catch-up if age 55+

(These amounts can be fully contributed even if the employer contributes a portion.)

Who’s Eligible to Use an HSA

You can contribute to an HSA if:

1. You’re covered by an HSA-eligible HDHP
2. You’re not enrolled in Medicare
3. You’re not claimed as someone else’s dependent
4. You don’t have disqualifying additional coverage

Bronze and Catastrophic plans in 2026 are expected to qualify, provided they meet the HDHP deductible & out-of-pocket requirements.

Why This Is a Big Opportunity

For individuals and families:

• Lower premiums of Bronze plans + tax-free savings = more flexibility
• You can build a long-term medical safety fund
• You keep the money forever — it’s yours, not the insurance company’s

For employers:

• Offers a lower-cost medical option without reducing benefits
• HSAs add a tax-efficient savings/retirement tool for employees
• Great way to enhance your benefits strategy without increasing premiums

Action Steps for 2026

Whether you’re an individual chooser or a business owner planning your benefits package, here’s what to do next:

1. Confirm your 2026 plan meets HDHP rules.
2. Open (or reopen) your HSA through a bank or financial institution.
3. Determine your contribution strategy for 2026 — monthly or lump sum.
4. Consider funding to the max ($4,400 / $8,750).
5. Educate employees if you’re an employer — most people still don’t understand how powerful HSAs really are.

The Bottom Line

The 2026 changes open the door for far more Americans to use an HSA — even those selecting lower-cost Bronze or Catastrophic plans. With the ability to contribute up to $8,750 (family) tax-free, this is one of the smartest financial tools available today.

If you want help reviewing your plan, determining eligibility, or planning your benefits strategy for next year, call our team at CorpStrat.

In 2025, employers are facing a perfect storm — rising healthcare costs, tighter labor markets, and an increasingly discerning workforce that expects more from their employers. For many small and midsize businesses, employee benefits have shifted from being a compliance exercise to a key strategic lever in attracting and retaining top talent.

At CorpStrat, we see this shift every day. Companies that treat benefits as a cost center are falling behind. Companies that treat benefits as a strategic investment are winning.

The New Benefits Reality

The U.S. benefits landscape is changing fast. Premiums continue to rise, plan designs are evolving, and employees are demanding transparency and flexibility. But the biggest change isn’t in the plans themselves — it’s in perception.

Employees now view benefits as a direct reflection of company culture and leadership priorities. When employees understand why their benefits exist and how those benefits support their personal and financial wellbeing, they’re more engaged, loyal, and productive.

That’s where the smartest employers are doubling down: not just on plan design, but on strategy, communication, and purpose.

What the Market Is Showing

Our benchmarking and benefits survey work has shown a clear trend: employers who regularly review and adjust their plans — instead of “set it and forget it” — are seeing measurable savings and stronger employee satisfaction.

Across industries, we’re seeing:

• Creative cost-sharing models that promote fairness and sustainability
• Self-funded and level-funded health plans gaining traction for flexibility and transparency for larger firms
• Voluntary benefits expanding as employees seek customization — from legal plans to long-term care
• And most importantly, better education on how to use benefits effectively

In a world where the average employee only spends minutes reviewing their benefits each year, communication is your single biggest competitive edge.

Three Tactical Moves Every Employer Should Make Now

1. Reframe Your Benefits Narrative

Stop listing benefits. Start telling a story.
Instead of “we offer health, dental, and vision,” say “we’ve built a program that protects your family’s health, finances, and future.”
Employees connect to outcomes, not line items.

Use every open enrollment, staff meeting, and onboarding moment to reinforce that message: your benefits are a cornerstone of your culture, not just paperwork.

2. Design for Cost Control and Flexibility

A one-size-fits-all approach is outdated.
Use data to benchmark your plans and find opportunities for smarter cost control — whether that means increasing employer contributions strategically, introducing HSA-compatible plans, or leveraging self-funded models.

This is where CorpStrat’s strategic benchmarking reports make the difference: we identify how your benefits compare to peers, spot cost anomalies, and align your plan design with your workforce demographics.

3. Communicate Like a Partner

Even the best plan fails if employees don’t understand it.
Use clear, visual, and frequent communication — not once a year at renewal. Send micro-communications that explain one feature at a time. Record quick videos. Host short “Benefits in 10 Minutes” sessions.

When employees understand their benefits, they make smarter choices. That reduces unnecessary claims, improves satisfaction, and lowers long-term costs — a win for everyone.

Why This Matters

In a competitive hiring market, benefits are one of the few levers you completely control. A strong program:

• Improves retention and reduces the cost of turnover
• Elevates morale and employer reputation
• Protects employees from financial risk — and helps their families feel secure
• Drives ROI, when employees actually use benefits as intended

When you invest in benefits strategically, you’re not just managing expenses — you’re investing in your culture, your brand, and your people.

What You Can Do This Week

1. Audit your benefits package — is it competitive, current, and aligned with your company story?
2. Benchmark your program with current market data to identify hidden opportunities.
3. Schedule a 20-minute strategy session with our CorpStrat team. Let’s look at how you can position your benefits to attract and retain the best talent in 2025.

Because the best time to rethink your benefits strategy is before your competitors do.

Closing Thought

The future of benefits isn’t about insurance. It’s about leadership.
When you view your benefits strategy as a reflection of how much you value your people — not just a business expense — you set your company apart.

At CorpStrat, that’s what we help employers do every day. Let’s build a smarter, more resilient benefits strategy together.