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:
- What if you end up in business with a widow or widower? (Succession planning)
- What if a business buy-out is forced upon you at the worst time?
- What if your top talent walks across the street to a competitor?
- What if the cost of replacing a senior executive breaks the bank?
- 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