Author Archives: Matt Schiff

A business is only as strong as the promises it keeps to its key people. In the world of high-growth, mid-cap companies: the "stocks under rocks" often highlighted in the Burkenroad Reports: talent is the primary engine of value. When we look at companies like Pool Corp (POOL), Haverty Furniture (HVT), Powell Industries (POWL), and Cal-Maine Foods (CALM), or financial institutions like First Bancshares (FBMS) and First Guaranty Bancshares (FGBI), we see organizations that have built incredible legacies.

But here is the universal truth: Your most valuable assets walk out the door every night. Whether they come back the next morning: and whether they stay for the next decade: depends on more than just a competitive salary. It depends on "Benefit Security."

At Schiff Executive Benefits, we specialize in Restoring Alignment and Retention. We’ve analyzed the public structures of these Burkenroad-profile companies to identify where executive benefits are performing at a high level and where "Operational Drift" might be putting the company: and the executive: at risk.

The "What If" That Keeps Presidents Up at Night

When I sit down with a President or a CEO, I often start with one of our core "What If" questions: What if your top talent leaves?

Think about the replacement cost. It’s not just the recruiter fee. It’s the lost institutional knowledge, the client relationships that follow the executive, and the momentum that stalls during a transition. For companies in the Burkenroad universe, where lean management teams often drive outsized results, the departure of a key leader isn't just a hurdle: it’s a headwind.

The solution isn't simply "more pay." It is about creating an Ownership Feel for those who don’t actually own shares, and providing a level of security that makes it impossible for them to look elsewhere.

Creating an "Ownership Feel" for Non-Owners

For corporations like Powell Industries or Cal-Maine Foods, retaining key managers requires a strategy that mirrors the rewards of ownership without the dilution of equity. This is where Phantom Stock or sophisticated Non-Qualified Deferred Compensation (NQDC) plans come into play.

By structuring a plan that tracks company performance or specific growth metrics, you give the executive a stake in the outcome. They begin to think like an owner because their long-term wealth is tied to the firm’s trajectory. However, a plan on paper is only as good as the funding behind it.

Many companies fall into the trap of "unfunded liabilities." They promise a benefit 15 years down the road but leave the bill for a future management team to pay. This creates a lack of security for the executive. They find themselves asking: Will the money actually be there when I’m ready to exit?

Benefit Security and the Power of Full Cost Recovery

This is where the conversation shifts from a human resources discussion to a balance sheet discussion. For the companies we’ve analyzed, such as First Bancshares and First Guaranty Bancshares, the use of Bank-Owned Life Insurance (BOLI) is a standard tool. For our corporate friends like Pool Corp and Haverty Furniture, the equivalent is Corporate-Owned Life Insurance (COLI).

The goal is Full Cost Recovery.

Most benefit plans are an expense. We view them as a strategic reallocation of assets. By using COLI or BOLI as an informal funding vehicle, the employer can recover:

1. The original premium paid into the plan.


2. The cost of the benefits paid to the executive.


3. The "opportunity cost" of the money (the interest the company could have earned elsewhere).

When structured correctly, the plan becomes "cost-neutral" or even "cost-positive" to the corporation while providing 100% protection to the employee's family and 100% of the promised income in retirement.

Retirement Made Simple: The Four Pillars

In my experience, executive benefit plans often become overly complex, leading to confusion and, ultimately, a lack of perceived value. We advocate for Retirement Made Simple. If an executive at Haverty’s or Powell Industries can’t explain their retirement plan to their spouse in two minutes, the plan is failing as a retention tool.

The Perfect Plan® (as we call our optimized approach) focuses on four fixed pillars:

• Fixed Dollar Amount: The executive knows exactly what they will receive.


• Fixed Period: The duration of the payments is defined and guaranteed.


• Fixed Rate of Return: No market volatility keeping the retiree awake at night.


• Fixed Cash Flow: A predictable stream of income that supplements the 401(k) limits.

When you offer "Retirement Made Simple," you remove the anxiety of "running out of money," which is one of our primary "What If" anchors. You can learn more about how we frame these outcomes by visiting our The Perfect Plan®.

Technical Compliance: Avoiding "Operational Drift"

One of the biggest risks we see in the Burkenroad companies is Operational Drift. A plan that was compliant and efficient in 2010 may be a ticking time bomb today due to changes in IRC 409A and IRC 101(j).

IRC 409A: The Safe Harbor Update

IRC 409A governs how and when deferred compensation is paid. The penalties for non-compliance are draconian: immediate taxation of all deferred amounts plus a 20% penalty tax on the employee. We often find that companies haven't updated their "Safe Harbor" language to reflect modern IRS guidance. If you haven't audited your NQDC plan in the last three years, you are likely drifting. You can watch a short overview of 409A compliance here.

IRC 101(j): The Notice and Consent Rule

For companies using COLI (Corporate-Owned Life Insurance) to fund these plans, compliance with IRC 101(j) is non-negotiable. If you do not obtain written consent from the executive before the policy is issued, the death benefit: which is supposed to be tax-free: becomes taxable income to the corporation.

Benchmarking the Burkenroad Peer Groups

When we look at the specific companies in this analysis, we see a range of maturity in their executive benefit structures.

• Financial Institutions (FBMS, FGBI): These banks generally understand BOLI but often lack a post-purchase analysis to ensure their peer group benchmarking is up to date. Are you holding too much cash in the plan? Is your BOLI/Capital ratio optimized?


• Retail and Industrial (POOL, HVT, POWL, CALM): These corporations often have "Legacy Plans" that are either under-funded or using outdated insurance products that don't offer the flexibility required for today’s executive.

The question isn't just "Do you have a plan?" The question is "Is your plan still doing its job?"

Restoring Alignment

The goal of any executive benefit strategy should be to align the interests of the shareholder, the company, and the key executive. When an executive at a company like Cal-Maine Foods knows that their family is 100% protected and their retirement is 100% secure, their focus remains on driving the business forward.

They aren't looking at the "next big offer" because they are already participating in The Perfect Plan®.

If you are a Center of Influence (COI) advising these companies, or an executive within one of these organizations, it’s time to move past the "set it and forget it" mentality. The economic environment has shifted, and your retention strategies must shift with it.

We invite you to retain your key people with ownership-like benefits and ensure your organization is protected against the "What Ifs" that matter most.

Sit back, grab your coffee, and let’s look at your plan together. We’re here to act as your guide through the complexities of executive security, ensuring your legacy: and the legacies of your top talent: are built on a foundation that lasts.

Come join us for Part 2, where we will dive deeper into the specific financial impact of "Full Cost Recovery" for the Burkenroad industrial sector.

Matt Schiff
President, Schiff Executive Benefits
Restoring Alignment and Retention

Common sense wins. Strong balance sheets do not happen by accident. And in this business, the future belongs to the institutions that fund tomorrow’s promises before those promises come due.

When you review the top U.S. life insurance carriers, one truth stands out quickly: the strongest players do not treat Insurance Company Owned Life Insurance (ICOLI) as an afterthought. They use it as a strategic balance-sheet asset. At Schiff Executive Benefits, that is exactly the lens we bring to every review. We reverse engineer goals, measure available capacity, and help leadership teams make decisions that restore alignment and retention.

Executive Summary

Analysis of Insurance Company Owned Life Insurance (ICOLI) holdings for the top 50 U.S. life insurance carriers. Focus: comparing admitted ICOLI assets against statutory surplus to identify industry benchmarks and individual carrier purchase capacity.

This report is designed for a peer review setting. It is formal in structure, practical in tone, and built to support executive discussion. The central question is simple: how are leading carriers using ICOLI to support long-term executive liabilities and non-qualified plan obligations while maintaining strong capital positions?

The answer matters. If the institutions that manufacture and distribute life insurance are also deploying it as a strategic internal asset, that is not coincidence. That is a benchmark.

Report Scope and Benchmark Framework

This analysis compares admitted ICOLI assets to statutory surplus across the top 50 U.S. life insurance carriers. The purpose is twofold:

• Identify where leading carriers currently sit on the ICOLI utilization curve


• Highlight potential additional purchase capacity based on peer positioning


• Provide a practical reference point for executive benefit funding discussions


• Frame ICOLI as a strategic tool rather than a passive holding

In plain English, this is about more than rankings. It is about capacity. It is about solvency. And it is about whether a carrier is using one of the most efficient balance-sheet tools available to support long-duration obligations.

Full Comparison Data Table: Top 50 U.S. Life Insurance Carriers

Strategic Insights

The market leaders are not using ICOLI casually. They are using it deliberately to fund long-term executive liabilities, support deferred compensation obligations, and create a more efficient funding mechanism for non-qualified plans. That matters because executive benefit promises are easy to make in a good year. Funding them responsibly over time is the real discipline.

What makes ICOLI especially attractive in the carrier environment?

• Balance-sheet efficiency: ICOLI can help offset long-duration executive obligations with a purpose-built asset.


• 0% RBC charge: Under applicable treatment, ICOLI can offer highly favorable capital treatment, which is a major reason sophisticated carriers continue to use it.


• Tax-advantaged growth: Policy cash value growth improves internal asset efficiency versus many taxable alternatives.


• Death benefit recovery: The life insurance chassis provides long-term cost recovery that supports employer economics.


• Plan funding flexibility: ICOLI works especially well when paired with non-qualified deferred compensation, supplemental executive retirement plans, and other targeted retention designs.

This is where the Schiff Method matters. We do not start with a product. We start with the goal. Then we reverse engineer the structure around the liability, the timeline, the culture, and the economics. That is how you build a plan that is not only technically sound, but also practical inside a real company with real people and real constraints.

If you are reviewing admitted ICOLI relative to surplus, you are really asking a sharper question: how much strategic capacity remains before a carrier reaches its own comfort threshold? That is the kind of question that keeps a peer review meeting productive.

Selected Carrier Commentary

New York Life

At $4.6 Billion in admitted ICOLI, New York Life stands out as one of the clearest industry benchmarks. Size alone does not tell the story. What matters is what that size signals: long-term confidence in ICOLI as a funding vehicle for executive liabilities and institutional promises.

MetLife

At $4.1 Billion, MetLife reflects the same disciplined use of ICOLI as a strategic balance-sheet asset. This is not window dressing. This is infrastructure.

MassMutual

At $3.0 Billion, MassMutual remains firmly in the top tier. The carrier’s position reinforces the broader takeaway that large, well-capitalized institutions continue to rely on ICOLI where efficiency and long-term liability management matter.

National Life Group

With approximately $615 Million in holdings, National Life Group shows meaningful participation while still leaving visible room for expansion relative to likely peer capacity bands.

Ameritas

Ameritas is especially notable from a peer review standpoint because our analysis indicates capacity for an additional $400 Million purchase. That does not mean a carrier should buy simply because it can. It means there is room to evaluate whether strategic underutilization is leaving value on the table.

Why This Matters Beyond the Carrier Space

Even though this report focuses on insurance carriers, the lesson travels well. The same core logic applies when corporations and partnerships use COLI to attract, retain, and reward key talent, fund non-qualified obligations, and prepare for the business “What Ifs” that can hit without warning.

That is why the peer review process is valuable. It turns abstract strategy into measurable comparison. It helps answer questions like:

• Are we underutilizing a highly efficient funding tool?


• Are we carrying long-term executive liabilities without a matching asset?


• Are we solving retention problems in a cost-effective way?


• Are we planning for replacement cost, retirement income, or ownership transition before the point of no return?

For leaders thinking bigger about non-qualified benefit design, The Perfect Plan® conversation is always about alignment first. Strategy second. Product last.

Conclusion

ICOLI continues to be a primary strategic vehicle for cost-effectively managing executive benefits and non-qualified liabilities across the life insurance sector.

That is the big takeaway from this peer review analysis. The strongest carriers continue to use ICOLI because it works. It supports long-term promises. It helps preserve capital efficiency. And it gives leadership teams a disciplined way to fund obligations before those obligations become pressure points.

If you want to evaluate how these same planning principles translate into executive benefit strategy, non-qualified design, or COLI implementation, we would be glad to walk through it with you. You can also explore more insights on our posts page or join us at The Perfect Plan®.

Restoring Alignment and Retention.

Time has a funny way of moving both slowly and at breakneck speed. They say the only constant in life is change, but in the world of executive benefits, the only constant is complexity. Today, as I sit in my office on this Wednesday, April 15, 2026, I’m reflecting on a journey that started exactly two decades ago.

In 2006, I made a choice that felt both terrifying and inevitable. I walked away from a comfortable role as Managing Director at NYLEX Benefits. I was managing a massive operation, hitting high-stakes premium goals, and overseeing regional directors. But I felt a pull toward something more personal, more technical, and frankly, more innovative. I wanted to build a firm where the "chief bottle washer" (that was me) was also the creative mind behind the most sophisticated plan designs in the industry.

Schiff Executive Benefits was born from that desire. And twenty years later, our mission remains the same: Restoring Alignment and Retention.

The Universal Truth of Growth

There is a universal truth in business: Growth without a plan is just a slow-motion collision with reality.

When we started SEB, the landscape was different. 409A regulations were the "new kid on the block" causing headaches for every C-suite in America. Fast forward to today, and while the regulations have evolved, the underlying anxiety for business owners hasn't changed. You still worry about the same things at 2:00 AM.

You worry about your legacy. You worry about your people. And you worry about the "What Ifs."

At Schiff Executive Benefits, we built our technical legacy by answering those "What Ifs" before they become "What Nows."

That legacy was built through a series of very real milestones:

• The Perfect Plan® PRESENTED BY MATT SCHIFF, CLU, CHFC, WMCP


• Schiff Executive Benefits (SEB)'s story


• Established Schiff Benefits Group May 2006 (after leaving NYLEX Benefits as Managing Director)
  
  
  • Managing Director NYLEX Benefits 1998-2006
  
  
  • Member Firm of NFP (Partners) 2006-2008
  
  
  • Valmark Member Firm 2009-2012 (Top 20 of 150 firms)
  
  
  • 12 Year MassMutual Executive Benefits Specialist (in MMEPA and MMGP)
  
  
  • Was a Member Firm of Lion Street in 2020 to 2022
  
  
  • Top Ten Firm with AgencyOne in 2024
  
  
  • Helped draft 409A and 101(j) in 2003 and 2005 as a ranking member of AALU's NQDC Committee with Michael Goldstein
  
  
  
  

The Five "What Ifs" That Keep You Up

Over the last twenty years, I’ve sat across the table from hundreds of CEOs, partners, and founders. Whether it’s a high-growth tech firm or a multi-generational manufacturing company, the questions are remarkably consistent. We frame our entire philosophy around these five what-if anchors:

1. What if you end up in business with your partner’s widow or widower? (The Succession Crisis)


2. What if you need to buy out a partner, but the cash isn’t there? (The Buy-Out Dilemma)


3. What if your top talent walks across the street to your biggest competitor? (The Retention Risk)


4. What if a senior executive retires, and the cost to replace them sinks your EBITDA? (The Replacement Cost)


5. What if you: the person who built it all: run out of money in retirement? (The Personal Risk)

If you haven't asked yourself these questions lately, now is the time. We call this the process of building The Perfect Plan®. It’s not just a catchy name; it’s a registered methodology designed to ensure that your business remains an asset, not a liability, to your family and your future.

A Technical Legacy: Beyond the 401(k)

Twenty years ago, many companies thought a robust 401(k) was enough to keep top-tier talent. We knew better. We’ve spent two decades educating the market on why a 401(k) is often a "math problem" for high earners. When you’re dealing with contribution limits, your most valuable people are often the most underserved.

Our technical legacy is rooted in the "Golden Handcuffs": strategies that actually work. We’ve specialized in:

• Non-Qualified Deferred Compensation (NQDC): Helping executives save significantly more than the standard $23,000 annual limit.


• Corporate Owned Life Insurance (COLI): Using institutional-grade insurance to fund future liabilities while providing tax-efficient growth.


• Split Dollar Arrangements: Creating sophisticated ways to provide life insurance benefits while retaining corporate control of the cash value.


• ESOPs and Buy/Sell Funding: Ensuring that when a transition happens, it’s funded with "discounted dollars" rather than current cash flow.

Innovation through Partnership: The Ridgeback Era

You can’t stay at the top of your game for twenty years by standing still. Sixteen months ago we took a massive leap forward by joining The Ridgeback Group as a founding firm.

Why? Because the technical demands of our clients were outpacing traditional consulting. By integrating AI-powered modeling systems, we’ve been able to automate plan management and maintain ongoing client tracking. One of the biggest mistakes I see in this industry is the "set it and forget it" mentality. A plan designed in 2018 might be completely irrelevant by 2026 if tax laws or interest rates shift. And we must practice whaat do for our client. 

Our partnership with Ridgeback ensures that The Perfect Plan® stays aligned with real-world change. It’s about using data to predict where the "Executive Sandwich" might squeeze your leadership team: the decade where they are simultaneously supporting aging parents and funding their children’s education. It’s the riskiest decade of their careers, and we have the technical tools to protect them through it.

More Than Just Numbers

While I love the technical side: the IRC 101(j) compliance, the 409A structuring, the complex math of 401(k) excess plans: this anniversary isn't just about spreadsheets. It’s about people.

I also can’t look back on twenty years without thinking about the milestone relationships that helped shape our path. Along the way, we’ve had the privilege of working with and alongside organizations like NFP, Valmark, MassMutual, Lion Street, and AgencyOne. Each chapter sharpened our perspective. Each relationship expanded our technical depth. And each one reinforced a lesson that still guides us today: no firm builds a lasting legacy alone.

I remember a client from about ten years ago: a founder of a major construction firm. He was terrified of what would happen if his son wasn't ready to take over. We sat down and walked through the "What Ifs." We implemented a COLI-funded buy/sell agreement and a deferred compensation plan that kept his key foremen on board for the transition.

Last year, he sent me a photo from his boat in Florida. He’s retired. His son is thriving. His foremen are still there. That is what I mean by Restoring Alignment and Retention.

A Dedication to Education: The American College of Financial Services

Jayne and Matt at the Solomon Huebner Award ceremony honoring Albert J. “Bud” Schiff.

Our commitment to technical mastery is rooted in a deep respect for education and the professional standards of our industry. This is perhaps best exemplified by our family’s long-standing relationship with The American College of Financial Services.

Founded in 1927 by Dr. Solomon S. Huebner—often called the "father of insurance education"—The American College is the nation’s largest non-profit educational institution dedicated to the financial services profession. For nearly a century, it has set the benchmark for excellence through its rigorous designations, including the CLU®, ChFC®, and MSFS. Huebner was also one of the first to champion holistic planning through rigorous fact-finding: the discipline of asking deeper questions before recommending any solution. Today, that approach is widely recognized as the gold standard for fiduciaries, but it is a principle designees of The American College have practiced since the institution’s inception.

It was a profound honor for our family when my father, Albert J. “Bud” Schiff, CLU, ChFC, AEP, was recognized with the Solomon Huebner Award in November 2013. This award is the College’s highest honor, presented to individuals who have made significant, lifelong contributions to the industry and the College’s mission. Here, my mother, Jayne, and I are pictured at the ceremony celebrating his legacy of leadership and his unwavering dedication to the advancement of professional knowledge in insurance services. In 2018, Jayne Schiff was also named a distinguished alum of The American College for Financial Services. That legacy of disciplined inquiry still shapes how we work today. It is why we begin with deep questions, not quick answers, and why our planning process is built around understanding the full picture before designing a path forward.

Celebration Photos

Celebrating 20 years of professional achievement and the trusted relationships that helped define our technical legacy.

Twenty years in, and the strongest milestones are still built around people, partnership, and time well spent together.

An elegant moment that reflects what twenty years in this business has always been about: trust earned, relationships maintained, and a legacy built the right way.

Great work rarely happens alone. This milestone is also a celebration of the network, conversations, and shared momentum behind the last twenty years.

Even in a highly technical field, relationships still matter most. That truth has carried Schiff Executive Benefits through every chapter of the last twenty years.

The Next 20 Years

As we celebrate this milestone, I’m often asked, "What’s next, Matt?"

The answer is simple: More innovation. The national debt is rising, tax rates are a moving target, and the competition for talent has never been more global. Whether you are a bank, a massive C-Corp, or a growing partnership, the need for sophisticated, technically sound executive benefits is only going to grow.

We are continuing to expand our video library to help demystify these complex topics. We are refining The Perfect Plan® to account for new economic shifts. And we are continuing to ask the hard questions that other consultants avoid.

A Note of Gratitude

To our clients: Thank you for trusting us with your legacy. To our partners: Thank you for your collaboration. To my team: Thank you for being the engine that drives this technical legacy forward.

I started this firm as the "chief bottle washer." Today, I’m proud to lead a team that sets the standard for the entire executive benefits industry.

If you’ve been wondering if your current plan is actually doing what it’s supposed to do: if it’s truly rewarding your best people while protecting your bottom line: let’s talk. No high pressure, no complex jargon without context. Just a conversation about your business and your future.

Sit back, grab your coffee, and when you're ready, come join us for the next chapter.

Here’s to twenty years of innovation, and to many more.

Matt Schiff
President, Schiff Executive Benefits

Want to see how we tackle these issues in real-time? Check out The Perfect Plan® Podcast for deep dives into the strategies that keep businesses thriving.

A business is only as good as the people who keep it running.

This is a universal truth that applies whether you are operating out of a garage with a $5 million revenue target or overseeing a multi-state enterprise crossing the $500 million mark. In the world of executive benefits, there is a lingering myth that sophisticated retention tools: the kind that create "golden handcuffs": are reserved exclusively for the Fortune 500.

The reality? The systems required to protect your most valuable assets don't care about the number of zeros on your balance sheet. They care about alignment.

At Schiff Executive Benefits, we’ve spent two decades proving that the "Schiff Method": a philosophy built on goal-oriented reverse engineering: scales perfectly. Whether you are a mid-market firm or a massive corporation, the technical depth required to attract and retain key talent remains the same. The only thing that changes is the scale of the solution.

The Myth of the "Too Small" Organization

Many leaders of $5M to $20M companies look at tools like Non-Qualified Deferred Compensation (NQDC) or Phantom Stock and think, "That’s for the giants. We aren't there yet."

But let’s ask a hard question: Is your "top talent" any less vital to your survival than a CEO is to a global conglomerate? If your key rainmaker or your operations mastermind walked out the door tomorrow, would the impact be any less devastating?

In many ways, the mid-market company is more vulnerable. A $500 million firm can often absorb the loss of a key executive through layers of redundancy. A $10 million firm might find itself in an existential crisis.

The systems we build: The Perfect Plan®: are designed to prevent that crisis. We don’t start with a product; we start with the "What If."

Reverse Engineering the Outcome

Most benefit brokers work forward. They look at what you have, add a percentage, and see where you land. We do the opposite. We reverse engineer from the finish line.

What does "realizing your dream value" look like for you? What keeps you up at night when you think about your professional legacy?

When we work with a $5 million company, we ask the same fundamental questions we ask a $500 million firm:

1. What happens if your top talent leaves for a competitor?


2. How do we ensure your senior executives have a cost-efficient retirement?


3. How do we create a buy-out structure that doesn't cripple the company?

By identifying the goal first, the technical solution: whether it’s a SERP (Supplemental Executive Retirement Plan), a split-dollar arrangement, or a COLI-funded NQDC: becomes the bridge to get there. The systems are the same. The math is just scaled to your specific revenue and headcount.

Enterprise-Grade Tools for the Corporate World

When we move away from the bank channel and look strictly at the corporate side, the flexibility of these systems is staggering. You don't need FDIC-regulated structures to build a world-class executive suite. You need technical depth.

1. Non-Qualified Deferred Compensation (NQDC)

For the $500 million firm, an NQDC plan might cover dozens of executives, allowing them to defer a portion of their compensation into a tax-advantaged environment. For the $5 million firm, this same system can be tailored for just two or three "must-keep" employees. It allows them to build wealth beyond the limits of a traditional 404(k) while keeping them aligned with the company’s long-term growth.

2. Phantom Stock and Equity Alignment

One of the biggest anxieties for mid-market owners is giving up actual equity. You’ve built this business from the ground up; you shouldn't have to slice up the pie just to keep people happy. Phantom Stock systems allow you to reward key players based on the increase in the company's value without ever handing over a single share of voting stock. It scales from the smallest partnership to the largest private corporation.

3. Corporate Owned Life Insurance (COLI)

To make these promises "stick," they need to be funded. This is where many plans fail. A $500M company understands that an unfunded liability is a ticking time bomb. We bring that same enterprise-level discipline to smaller firms through COLI. By using COLI to informally fund these obligations, the company creates a tax-efficient asset that can offset the costs of the benefits provided. It provides the "security" and "guarantee" that top-tier talent demands before they commit their next ten years to your vision.

Addressing the "5 What Ifs"

Regardless of revenue, every business owner faces the same five fundamental anxieties. At Schiff Executive Benefits, these are our primary anchors:

• Business with a widow: What happens to your succession plan if a partner passes away?


• Business buy-out: Do you have the liquidity to handle a transition without selling the farm?


• Top talent leaving: Have you built a "moat" around your most important people?


• Senior exec retirement: Are your replacement cost efficiencies optimized?


• Running out of money: Is your personal retirement as secure as your business’s future?

When you look at your company through the lens of these questions, the size of your revenue becomes secondary to the stability of your infrastructure. Our job is Restoring Alignment and Retention by ensuring that your corporate goals and your executives' personal goals are moving in the exact same direction.

Why Technical Depth Matters

In an unstable economic environment, "good enough" benefits don't cut it anymore. High-performers are looking for sophisticated, structured, and legally sound plans. They want to know that their 409A plans and buy/sell arrangements have been vetted by experts who understand the nuances of the tax code and corporate law.

This is where the "Schiff Method" shines. We don't just hand you a folder and wish you luck. We provide the technical depth to ensure your plan remains compliant and effective as you scale. If you grow from $5M to $50 million, your plan should grow with you: not become a liability that needs to be torn down and rebuilt.

Building It Your Way

You’ve worked too hard to settle for "off-the-shelf" benefit packages that don't fit your culture or your cash flow. Whether you are managing a small team of elite specialists or a massive workforce across the country, your retention strategy should be as unique as your business.

Are you worried that you're "too small" for high-end executive benefits? Or are you a large firm wondering if your current systems are actually as efficient as they could be?

It’s time to move past the guesswork. It’s time to apply enterprise-grade logic to your retention challenges.

Come Join Us

If you’re ready to see how these systems can be tailored to your specific scale, I invite you to sit back, grab your coffee, and let’s have a real conversation about your legacy.

You can explore more about our approach through The Perfect Plan® Podcast or dive into our specific services to see how we’ve helped companies across the revenue spectrum secure their future.

Your people are your greatest asset. Isn't it time you treated them like it?

Schiff Executive Benefits: Restoring Alignment and Retention.

For more information on how we scale sophisticated corporate benefits, visit our posts feed or contact our team directly to discuss your specific needs.

They say that to know where you are going, you first have to know where you came from. In the world of executive benefits and financial architecture, many people lead with spreadsheets, tax codes, and actuarial tables. But if you sit down with me for more than five minutes, you’ll realize that while I live and breathe the technicalities of IRC 409A and the complexities of deferred compensation, my "why" isn’t found in a ledger. It’s found in a legacy.

I’ve always viewed myself as an architect. Not of buildings, but of security. This mindset wasn’t something I picked up in a textbook; it was woven into the fabric of my life long before I founded Schiff Executive Benefits. It’s a mindset rooted in family, a passion for protection, and a deep respect for the hard work required to build a business that lasts.

The Multi-Generational Foundation

My journey in this industry isn’t just a career path; it’s a family tradition. Between my parents and myself, we represent nearly 150 years of collective experience in the financial services and insurance world.

Growing up, I watched my parents, Jayne and Bud Schiff, navigate the complexities of this business with a single-minded focus: taking care of people. They didn’t see clients as policy numbers; they saw them as families and businesses whose futures depended on the quality of our advice. That sense of responsibility stayed with me. It’s why I don’t just "sell" a plan: I architect a solution.

Jayne and Bud built more than a career legacy. They built a standard. Their example taught me that when you help protect a family, a business, or a future, you are doing deeply personal work. That legacy still shapes the way I serve clients today.

Today, that legacy continues with the unwavering support of my wife, Nancy, our CMO, The Ridgeback Group, our support team, and family legacy in our five children (Courtney and Jason, Alex, Ty, and Gavin).  They are the daily reminder that every decision has a human side. When we talk about protecting a business, we are really talking about protecting the people behind it and the families counting on them.

Caption: The foundation of everything we do: the Schiff family legacy, built on protection, care, and continuity across generations.

The 2006 Pivot: Building Something Better

By the mid-2000s, I had achieved what many would consider the pinnacle of corporate success. As a Managing Director at NYLEX Benefits, I had helped grow a team from five to thirty-five people and was deeply entrenched in the high-level world of Executive benefits, Bank Owned Life Insurance (BOLI) and other corporate-owned strategies.

But I felt a pull toward something more personal, as well as a work/life balance. I wanted to build a firm where technical innovation met human-centric service: where we could be nimble enough to solve the most complex executive retention issues while remaining deeply connected to our clients' personal missions, and still be connected to my family. 

In May of 2006, I made the leap and founded Schiff Benefits Group. It was a pivotal moment. I wasn't just starting a company; I was creating a platform to implement the strategies that would eventually evolve into The Perfect Plan®.

Looking back, the timing was critical. The world was about to face the 2008 financial crisis, and the regulatory environment was shifting rapidly. My experience in the "big corporate" world gave me the technical expertise to navigate IRC 409A and other compliance minefields, but it was my passion for individual business owners that drove the firm forward.

A Passion Beyond the Spreadsheets

If you follow me on social media or listen to The Perfect Plan® Podcast, you know that my life isn't just about Corporate Owned Life Insurance (COLI) and ESOPs.

I am a lover of music, particularly the soulful, grounded sounds of "The Immediate Family." There is a rhythm to great music, a harmony where every instrument must be in sync to create a masterpiece. I see business planning the same way. If your estate plan isn't in harmony with your buy/sell agreement, or if your deferred compensation plan isn't aligned with your retention goals, the "music" of your business falls flat.

Away from work, I stay busy with a few lifelong passions that have always kept me grounded: sailing, soccer, and golf. Sailing has long been a personal passion of mine. It teaches patience, awareness, adjustment, and respect for conditions you cannot control. Soccer brings energy, teamwork, and constant movement. Golf demands discipline, focus, and humility. Different games. Same lesson. You need a plan, and you need to stay aligned when conditions change.

Caption: Fifteen years of friendship, teamwork, and shared passion for the game, reflecting Matt’s lifelong love of soccer and the bonds he builds along the way.

My goal is to bring that harmony to your professional and personal life. I want to help you solve what I call the "5 What Ifs" that keep business owners awake at night:

1. What if you end up in business with a widow or widower? (Succession planning)


2. What if a business buy-out is forced upon you at the worst time?


3. What if your top talent walks across the street to a competitor?


4. What if the cost of replacing a senior executive breaks the bank?


5. What if you run out of money in retirement because you were too busy building the business?

Restoring alignment and retention isn't just our tagline; it's the rhythm we live by. We solve these "What Ifs" through technical mastery, but we frame them through the lens of protection for the families and legacies depending on you.

The Architect and The Perfect Plan®

When I call myself the "Architect of The Perfect Plan®," it’s not because I believe in a one-size-fits-all solution. Quite the opposite. Every architect knows that while the laws of physics (or tax codes) remain constant, the house must be built for the family living inside it.

The Perfect Plan® is a philosophy. It is a commitment to ensuring that every piece of your executive benefits package: from Executive Deferral Plans to Split Dollar arrangements to estate planning: is working toward a singular goal: your security.

We explore these concepts in depth on The Perfect Plan® Podcast, where we bridge the gap between technical strategies and real-world application. Whether we are discussing portable peace of mind or the nuances of business succession, the focus is always on the human element.

Why Experience Matters Now More Than Ever

We are currently navigating an era of "The 63% Exit Wave," where a massive generation of business owners is looking toward the horizon. At the same time, tax laws are in flux, and the competition for talent is fiercer than ever.

In this "unstable" environment, you don't just need a consultant; you need a guide who has seen the cycles before. Having been in this seat since 1992, and having lead Schiff Executive Benefits through two decades of economic shifts, I’ve learned that the best defense is a well-architected offense.

Whether we are working with a closely held family business on family wealth transfer and executive retention, a community bank on BOLI strategies or a global corporation on restoring executive alignment, the mission remains the same: Aligning a plan that fits the culture and legacy of the company tax efficiently, as well as is flexible for future needs.

Come Join Us

I often tell my clients to "sit back and grab your coffee" because these conversations shouldn't be stressful: they should be empowering. When you have a plan that addresses the technical "haunts" of the past and the "what ifs" of the future, you gain the freedom to focus on what you love: whether that’s growing your company, sailing, playing soccer or golf, or spending time with family.

My family legacy is one of protection. I’d love to help you secure yours.

If you’re ready to see how the "Architect" mindset can transform your business, I invite you to explore our latest insights or join the conversation over on The Perfect Plan® Podcast.

Let’s build something that lasts, together.

Matthew E. Schiff, CLU, ChFC, WMCP
President, Schiff Executive Benefits

Change is the only constant in life, yet we spend the majority of our professional careers trying to build a fortress of stability. We work late, we climb the ladder, and we take comfort in the "benefits package" listed in our employment contracts. But here is an undeniable truth that many executives realize too late: If you don't own it, you don't control it.

Most corporate benefits aren't actually yours. They are "leased" from your employer. And just like a leased car or a rented apartment, those benefits can be taken back the moment the lease is up, whether that’s through a job change, a layoff, or your eventual retirement.

At Schiff Executive Benefits, as we celebrate our 20th anniversary of Restoring Alignment and Retention, we’ve seen too many high-performers discover that their family’s financial safety net was tied to a desk they no longer sit at. If your peace of mind is contingent on your current HR department, you don't have peace of mind. You have a temporary arrangement.

The Illusion of the Corporate Safety Net

Let’s be real: when you look at your total compensation, the "group" benefits, life insurance, disability, and health coverage, look great on paper. They are often low-cost or even "free" to you. But in the world of high-stakes financial planning, free can be the most expensive price you’ll ever pay.

The problem with "leased" benefits is the lack of portability. We call these "weakest links" because they fail exactly when you need them most. Think about the Executive Sandwich: that decade where you are at your career peak, but also the "riskiest" decade for your family. You’re supporting aging parents and children’s tuition, all while maintaining a lifestyle that requires a high, steady income.

![Portable executive benefits and family security illustration]

What happens if you leave that role?

• Your Group Term Life Insurance: Usually vanishes or offers a "conversion" option that is so prohibitively expensive it’s practically useless.


• Your Group Disability: Gone. And if your health has changed during your tenure, you may find yourself uninsurable on the private market.


• Your Retirement Gap: You might be hitting the 401(k) cap, leaving a massive void between your current lifestyle and what your "leased" plan will actually provide.

The Five "What Ifs" of Executive Security

In our two decades of consulting, we’ve narrowed the risks down to five core "What If" questions. If you can’t answer these with a definitive "I’m covered regardless of my employer," then your plan is in jeopardy.

1. What if there’s a business buyout? If your company is sold, the new owners may not value the same benefit structures. Your "leased" security could disappear overnight in a merger.


2. What if you are the top talent leaving? Whether you’re moving to a competitor or starting your own firm, you shouldn’t have to leave your family’s protection behind.


3. What if you run out of money in retirement? Most leased benefits end at age 65. If you live to 95, who is covering the risk for those final 30 years?


4. What if your successor costs more than expected? For the business owner, not having portable, owned benefits (like COLI) means the cost of replacing talent can skyrocket.


5. What if you have to deal with a widow/widower (succession)? Without portable, owned life insurance structures like TOLI (Trust Owned Life Insurance), the transition of a business can be catastrophic for the surviving family.

Moving from "Leased" to "Owned" with The Perfect Plan®

![The five what-ifs of executive security planning]

So, how do we move from the fragility of "leased" benefits to the "Portable Peace of Mind" that ownership provides? It starts with a shift in philosophy. You need to treat your executive benefits with the same rigor you apply to your personal investment portfolio.

This is where The Perfect Plan® comes into play.

The Perfect Plan® isn't a single product; it’s a strategic framework designed to align the interests of the corporation and the executive. By utilizing structures like Corporate Owned Life Insurance (COLI) and Non-Qualified Deferred Compensation (NQDC), we can create benefits that are:

• Portable: They stay with you, providing a continuous "security blanket" regardless of your employment status.


• Tax-Efficient: They leverage the power of tax-deferred growth to solve the retirement gap created by 401(k) limits.


• Discriminatory (In a good way): Unlike group plans, these can be customized specifically for the key leaders who drive the company’s success.

When we design The Perfect Plan®, we look at the "What Ifs" and solve them one by one. We ensure that the death benefit is there to protect your family, the cash value is there to supplement your retirement, and the disability coverage is own-occupation and portable.

The Corporate Perspective: Alignment and Retention

If you are a business owner or a board member, you might be wondering: "Why would I want my executives’ benefits to be portable? Doesn’t that make it easier for them to leave?"

It’s a fair question. But the reality is the opposite. Our tagline, Restoring Alignment and Retention exists because we know that top talent stays where they feel truly secure and valued.

When you provide a "leased" benefit, the executive knows it’s a temporary hook. When you facilitate "ownership" through a properly structured executive benefit plan, you are providing a sophisticated wealth-building tool that demonstrates a long-term commitment to that leader’s family. You aren't just giving them a job; you are helping them build a legacy.

Furthermore, using COLI (Corporate Owned Life Insurance) to fund these obligations allows the corporation to recover the costs of the benefits over time. It’s a win-win that "leased" group plans simply cannot match.

![Corporate alignment retention and family security meeting]

Why Now? The Point of No Return

We are currently in a shifting economic landscape. National debt is rising, tax laws are perpetually on the chopping block, and the "war for talent" has never been more intense.

If you wait until you are 60 to realize your life insurance is "leased," you may find that your health or the sheer cost of private coverage makes it impossible to pivot. There is a "point of no return" in financial planning where the math simply stops working in your favor.

Don't let your family’s security be the weakest link in your professional life. You’ve worked too hard to leave your peace of mind in someone else's hands.

Join the Conversation

As we celebrate 20 years at Schiff Executive Benefits, we invite you to take a closer look at what you actually own. Are your benefits a permanent foundation, or are they just a temporary arrangement?

Sit back, grab your coffee, and think about the five "What Ifs." If the answers make you a little uneasy, it’s time to start a different conversation. You can explore our video library to see how these strategies work in practice, or browse our latest insights to stay ahead of the curve.

Your career is about more than just a paycheck; it’s about the legacy you leave for those you love. Make sure that legacy is built on ownership, not a lease.

Come join us, and let’s build The Perfect Plan® for your future.

The only thing more certain than change itself is the uncertainty of how long we will actually need our money to last.

For the better part of forty years, you’ve likely been a world-class accumulator. You’ve watched the markets, maximized your contributions, and built a nest egg designed to stand the test of time. But eventually, the clock strikes a different hour. The game changes from "how much can I grow?" to "how much can I safely spend?"

It’s the transition from the climb to the descent, and as any seasoned mountaineer will tell you, the descent is where most accidents happen. In the world of executive benefits and private wealth, we call this transition "Retirement Paycheck Design."

At Schiff Executive Benefits, as we celebrate our 20th anniversary of Restoring Alignment and Retention, we’ve found that the biggest anxiety keeping high-achieving leaders up at night isn't just market volatility, it’s the "What If" questions. Specifically: What if I run out of money before I run out of time?

The Psychological Shift: From Harvest to Table

There is a profound psychological hurdle in moving from a steady salary to a manufactured paycheck. When you are the one signing the checks for a corporation or a partnership, you understand cash flow. But when the business is no longer the primary engine of your personal wealth, where does the first dollar come from?

The Perfect Plan® isn't just about having the money; it’s about the sequence of how you access it. If you pull from the wrong bucket at the wrong time, you’re not just spending your money, you’re spending your future’s ability to generate more of it.

The Hierarchy of Income: Where to Start?

Think of your retirement income as a tiered fountain. You want to drink from the overflow before you start dipping into the reservoir. To design a sustainable retirement paycheck, we look at a three-layer approach.

1. The Foundation: Predictable and Guaranteed Income

The first layer of your paycheck should always come from sources that are "set and forget." These are the stabilizers of your lifestyle.

• Social Security: While often a smaller portion of an executive’s total cash flow, it remains the bedrock of inflation-indexed, guaranteed-for-life income.


• Pensions: If you are among the few who still hold a traditional defined benefit plan, this is your primary engine.


• Required Minimum Distributions (RMDs): Uncle Sam eventually demands his cut. Since you must take this money from your traditional IRAs or 401(k)s, it should be the first discretionary bucket you empty.

2. The Yield: Living on the "Golden Eggs"

The ideal retirement paycheck stays within the income generated by your portfolio to preserve the principal. As the old saying goes, you want to live on the golden eggs without having to kill the goose.

• Dividends and Interest: High-quality bond ladders and dividend-paying stocks provide a natural "overflow" that doesn't require selling shares during a market downturn.


• Corporate Owned Life Insurance (COLI) & NQDC: For the executive who has utilized Non-Qualified Deferred Compensation (NQDC), these distributions can be timed to bridge the gap between early retirement and the start of RMDs.

3. The Reserve: Strategic Principal Drawdown

Only after exhausting the foundation and the yield should you look toward selling assets. This is where most people get into trouble. Selling during a "down" year in the market can create a "sequence of returns" risk that is nearly impossible to recover from.

The "What If" Scenarios for the Corporate Leader

As part of our April “5 What Ifs” campaign, we are diving deep into the questions that define a legacy. When we talk about retirement paycheck design, two of our core "What If" questions take center stage:

What if you run out of retirement money?
This is the ultimate fear. By utilizing The Perfect Plan®, we look at tax-advantaged vehicles like COLI and Split Dollar arrangements that provide a "buffer" asset. If the market is down, you don't sell your stocks; you take a tax-free loan or distribution from a cash-value policy to fund that year’s paycheck. This allows your equity portfolio the time it needs to recover.

What if a senior executive retires and you haven't planned for the replacement cost?
From the perspective of the company, retirement paycheck design isn't just for the individual; it’s a corporate liability. How are you funding the promises made to your top talent? If you haven't used cost-recovery strategies like COLI, the "paycheck" you owe a retiring partner could put a massive strain on the company’s current cash flow.

Attracting and Rewarding Talent Through Design

Retirement paycheck design isn't just a "end of career" conversation. It’s a recruitment tool. When you are looking to attract the next generation of leaders to your corporation or partnership, showing them The Perfect Plan® that includes supplemental executive retirement plans (SERPs) is a game-changer.

You aren't just offering them a high salary today; you are offering them a designed, tax-efficient exit strategy for tomorrow. This is how you bridge the Executive College Funding Gap and ensure that their "peak career years" aren't also their "riskiest financial decade."

The Strategic Order of Operations

So, where should your income come from first? The answer is: The source that is most "tax-perishable" or legally mandated.

1. Mandated Income: RMDs and Social Security.


2. Tax-Heavy Income: Distributions from fully taxable deferred compensation plans.


3. Tax-Advantaged Income: Tax-free distributions from COLI or Roth accounts.


4. Portfolio Yield: Interest and dividends.


5. Principal: Last resort.

By following this order, you maximize the "shelf life" of your most productive assets. You allow your growth-oriented investments to stay in the market longer, compounding over time, while you live off the structures specifically designed for distribution.

Restoring Alignment and Retention

At Schiff Executive Benefits, we believe that a paycheck is more than just a deposit in a bank account: it’s a reflection of a life’s work. Whether you are a business owner looking at your own "What If" scenarios or a CEO trying to solve the Executive Sandwich problem for your team, the design matters.

Designing The Perfect Plan® requires a team of advisors who understand that your needs as an executive are different than the average employee. You have higher tax stakes, more complex regulatory hurdles (like 409A compliance), and a much smaller margin for error when it comes to "replacement cost efficiency."

Come Join Us

Are you confident in the sequence of your future retirement paycheck? Or are you worried that a single market correction could force you to "kill the goose"?

Take a moment to sit back, grab your coffee, and think about your own "What Ifs." We’ve spent the last 20 years helping leaders like you navigate these unstable financial environments with authority and empathy.

If you’re ready to move beyond the standard 401(k) and start building a paycheck design that actually works when you need it most, we invite you to explore our video library or browse our latest insights.

Let’s ensure your legacy is one of security, not uncertainty.

Warmly,

Matt Schiff
President, Schiff Executive Benefits

Time has a funny way of making the urgent feel ancient. In the world of executive benefits, the year 2008 usually conjures up memories of market volatility and the Great Recession. But for those of us in the trenches of financial consulting, 2008 represents a different kind of milestone: the final deadline for Section 409A compliance.

It is often said that the greatest threat to a well-laid plan is not a sudden storm, but a slow, quiet drift. We see it every day at Schiff Executive Benefits. A plan that was perfectly calibrated eighteen years ago is now operating on autopilot, while the business it serves has changed completely.

If you are a CEO, a CFO, or a business owner, you likely remember the scramble of 2008. You worked with your lawyers and consultants to ensure your nonqualified deferred compensation (NQDC) plans, your severance agreements, and your stock options were all brought into "operational compliance." You signed the documents, filed them away, and got back to the business of growing your company.

But here is the universal truth that keeps many executives up at night: The IRS does not care about your good intentions. Section 409A is a strict liability regime. If your written plan says one thing and your payroll department does another, the penalties aren’t just a slap on the wrist. They are a financial catastrophe for your top talent.

The Ghost in the Machine: What is the 2008 Plan Trap?

The "2008 Plan Trap" is the widening gap between the legal language written during that compliance rush and the actual day-to-day administration of those benefits today. In 2008, companies were given a firm deadline of December 31 to amend their plans to meet 409A standards. Many did so under duress, adopting boilerplate language just to cross the finish line.

Since then, almost two decades have passed. In that time:

• Key executives have retired or been replaced.


• The business has likely undergone mergers, acquisitions, or restructuring.


• Vesting schedules have been modified "on the fly" to accommodate retention needs.


• Payment triggers have been adjusted to help an executive through a personal transition.

Every one of those "minor" adjustments, if not reflected exactly in the plan document, is a 409A violation waiting to be discovered.

Why 409A Compliance Still Haunts You

You might think, "It’s been eighteen years and we haven't had an issue. Why now?"

The answer lies in the increasing sophistication of IRS audits and the standard due diligence performed during business transitions. If you are looking to sell your company or merge with a larger entity, the very first thing the buyer’s counsel will look at is your executive benefit stack. If they find a 409A violation, it can stall the deal or lead to significant holdbacks in the purchase price.

The penalties for 409A non-compliance are draconian. When a plan fails:

1. Immediate Taxation: All amounts deferred under the plan (and all similar plans) become immediately taxable to the executive, even if they haven't received a dime.


2. The 20% Penalty: A flat 20% additional federal income tax is applied to the deferred amount.


3. Premium Interest: An interest penalty is assessed based on when the money should have been taxed.


4. State Penalties: In many states, like California, additional state taxes (often 5%) are piled on top.

For a top executive with a seven-figure deferral balance, a 409A error can result in a tax bill that wipes out over half of their benefit. Imagine explaining to your most valued leader that the "reward" you promised them is now a liability because of a paperwork mismatch from 2008.

Restoring Alignment and Retention

At Schiff Executive Benefits, we focus on Restoring Alignment and Retention. We believe that executive benefits should be a source of security, not a source of anxiety. This is why we developed The Perfect Plan®.

The Perfect Plan® is our proprietary approach to ensuring that your benefits aren't just compliant on paper, but are actually performing the way you intended. Whether you are dealing with deferred compensation, Corporate Owned Life Insurance (COLI), or Split Dollar arrangements, the goal is the same: absolute clarity.

When was the last time you asked yourself the "5 What Ifs" that anchor a legacy?

1. What if you had to do business with your partner's widow? (Succession)


2. What if you needed to buy out a partner unexpectedly?


3. What if your top talent left for a competitor tomorrow?


4. What if a senior executive retired and the replacement cost was double what you expected?


5. What if you or your executives ran out of money in retirement because of tax-inefficient planning?

The 2008 Plan Trap directly impacts question number three and four. If your 409A compliance is compromised, your ability to retain top talent vanishes the moment they realize their "golden handcuffs" are actually a tax time bomb.

Beyond the Bank: 409A for Corporations and Partnerships

While many associate high-level benefit consulting with the banking industry, these traps are just as prevalent: if not more so: in general corporations and partnerships. Whether you are managing an ESOP or navigating buy/sell arrangements, the administrative drift is a universal threat.

We often see this in Corporate Owned Life Insurance (COLI) structures. COLI is an incredible tool for financing executive benefits and providing a tax-efficient recovery of costs. However, if the underlying plan it funds: the NQDC: is out of sync with 409A, the COLI asset becomes a mismatch for a broken liability.

As we celebrate our 20th anniversary at Schiff Executive Benefits, we’ve looked back at thousands of plans. The most successful ones aren't the ones with the most complex formulas; they are the ones that have been consistently reviewed, audited, and aligned with the current goals of the leadership team.

How to Escape the Trap

If your plan documents haven't been reviewed since the late 2000s, you are likely sitting on a compliance ghost. Here is how we suggest you approach the "security check":

1. Audit the "Actuals": Don't just read the plan document. Look at the last three years of payroll records for your deferred compensation. Do the payment dates match the document? Does the vesting match the ledger?


2. Review the Definition of "Separation from Service": This is one of the most common 409A triggers. If an executive "retires" but stays on as a consultant, they may have technically separated from service. If the plan didn't pay out, or if it paid out when it shouldn't have, you have a violation.


3. Check Your COLI Alignment: If you are using COLI to fund these benefits, ensure the policy performance is still tracking with the growth of the liabilities. Market shifts since 2008 have been significant.


4. Modernize with The Perfect Plan®: Use a structured framework to bring all your executive benefits: including estate planning and succession strategies: into a single, cohesive narrative.

The Point of No Return

There is a "point of no return" in 409A compliance. Once an audit begins or a transaction is underway, your ability to "fix" a mistake without incurring penalties is almost non-existent. The IRS does offer correction programs (like Notice 2008-113), but they are only available if you find the error before they do.

Why leave the legacy of your business to chance? Why let a paperwork error from nearly twenty years ago threaten the financial security of the people who helped you build your company?

We invite you to take a breath and look at your benefits through a fresh lens. Executive benefits shouldn't be a "trap." They should be the foundation of your employee retention strategy and a cornerstone of your professional legacy.

If you’re wondering if your current plan is still The Perfect Plan® for your business in 2026, let's talk. Sit back, grab your coffee, and let’s walk through the "What Ifs" together. We’re here to help you navigate the complexities of the modern financial environment with the authority and empathy that twenty years of experience provides.

Come join us in ensuring your executive benefits are a guarantee of your future, not a haunting from your past.

For more insights into executive retention and tax-efficient planning, visit our services page or explore our latest posts at Posts.