By Colleen Weber, CFP®, CPA

No matter your age, profession, or personal circumstances, understanding taxes can be a challenge—especially for corporate executives. Despite your success, intelligence, and drive, navigating the complexities of taxes can still be overwhelming, particularly when it comes to managing your executive benefits. Even with a high income and business experience, fully leveraging tax-saving strategies can be tricky.

Here are the top 4 tax challenges executives face, along with proactive steps you can take to manage them effectively.

1. Understanding Your Deferred Compensation

For executive employees, deferred compensation plans can be a good way to save for retirement because they have no contribution limits. But the intricacies of these plans can be difficult to understand, especially as it relates to your tax bill.

Deferred compensation allows a portion of current earnings to be delayed until a later date (typically retirement) in order to avoid taxation in the current year. Since they have no contribution limits, they are especially attractive to executives and high-earning employees, particularly if they anticipate being in a lower tax bracket in retirement. 

Keep in mind that while you are receiving tax deferral through this benefit, The reason you are able to receive preferential tax treatment is because your employer simply “promises” to pay your compensation down the line; they are not legally obligated to keep this promise and may be unable to if they experience financial instability or bankruptcy in the future. When thinking about deferred compensation, be sure to assess your company’s viability and how it could affect your compensation in the future.

How and when to take your deferred compensation payout is another big question. Most plans allow you to take the payout as a lump sum (which could create a huge tax liability all in one year), or you can choose to take fixed annuity payments over the course of a set period of time (causing your tax liability to be spread out over several years). The best option to choose will depend on your specific financial situation, including other sources of retirement income, annual expenses, and long-term goals.

2. Accessing Cash From Illiquid Investments

As executive employees, many of my clients receive equity compensation, including stock options and restricted stock units (RSUs). I’ve found that they often don’t fully understand how these fit into their overall tax plan or when they can be converted to cash.

Stock options, for instance, can be exercised at any point after they are received. Once exercised, they can be sold on the open market for cash. The amount of tax due will depend on the type of stock option received (incentive or nonqualified) and how long the stock was held before sale.

RSUs, on the other hand, are subject to vesting schedules based on length of employment or performance, and once the RSU has become fully vested, it’s usually converted to stock. At this point, you will be taxed on the market value of the converted shares. Understanding when this will happen is crucial to minimize your tax liability. For instance, if you expect a large portion of your RSUs to vest next year, you should try to minimize or defer other income to a different year so you’re not pushed into the next tax bracket.

If your RSUs don’t convert automatically, then deciding when to convert your options to stock becomes the question. Converting at the right time can help boost your returns and reduce tax liability. Waiting until share prices are depleted or when your taxable income is lower is often a great way to maximize your RSUs.

It’s also important to think through what you want to do with the stock once it has become available. Selling it within one year of conversion may result in capital gains that will be taxed as ordinary income, whereas holding it for at least a year will allow any gain to be taxed at the preferential, long-term rate. Either way, fully integrating your equity compensation into your wealth management plan is a necessary step. 

3. Diversifying a Concentrated Position

Many executives have built wealth through concentration in their company stock (through the equity compensation mentioned above), but few are able to preserve wealth over time while in such heavily concentrated positions. Worse yet, for too many, their stock never hits their anticipated peak, leaving their financial goals underfunded.

If the company performs poorly or there is an overall bear market, it will depress the stock price and you could be laid off at the same time. Without a solid wealth management plan, your personal income statement and balance sheet could be blown up all at once. 

Unfortunately, history has many examples of this happening to corporate executives. Back in 1999 when Enron filed for bankruptcy, more than $1 billion in employee retirement savings simply evaporated. During the financial crisis in 2008, many Lehman Brothers employees experienced the same thing.

Diversification is necessary, but it can come with an unwanted tax liability, especially if your company stock is selling for much higher than it was worth when you received it. There are many tax-efficient ways to diversify a concentrated portfolio, including exchange funds, options, and charitable trusts. You could also implement a phased approach to diversification where you slowly sell off your company stock to spread the tax liability over several years.

4. Maximizing Retirement Contributions

Just because you are an executive employee with a high level of income doesn’t mean that maximizing retirement contributions is easy. In fact, it’s another tax obstacle I’ve seen many executive employees face.

Annual contribution limits for retirement accounts are usually too low for you to make meaningful advances toward your retirement wealth. For example, the contribution limit to a 401(k) in 2025 is $23,500 (plus an additional $7,500 if you’re over 50; or a new “super catch-up” of $11,250 if you’re 60-63). The contribution limit to a traditional IRA is only $7,000 (or $8,000 if over 50). 

Experts recommend that most people should contribute at least 15% of their income toward retirement, so we’ll use that benchmark as a simple example. If you earn $500,000 per year, you would need to contribute $75,000 per year to meet that 15% goal. Maximizing contributions to a 401(k) and a traditional IRA don’t even come close, so high-income earners need to find creative ways to save for retirement.

Additional forms of retirement savings can come from deferred compensation or equity compensation, each with their tax challenges. You can also utilize a taxable investment account, but this may generate income and gains before retirement that will be taxable as current income. Avoid tax pitfalls by working with a qualified financial professional who can help you create a retirement savings plan based on your specific income level and future needs.

How I Can Assist You

As both a CPA and a CFP^®, I specialize in helping corporate executives navigate the complexities of their finances, from tax strategies to executive compensation planning. Your financial picture is already intricate—taxes shouldn’t add to the stress. My expertise allows me to help you avoid common tax planning pitfalls and implement proactive strategies that align with your financial goals.

Let me and my team at Colleen Weber CPA, CFP^® guide you toward a tax-efficient strategy that helps optimize your wealth. To get started, book a free introductory meeting online or call (952) 470-0750.

About Colleen

Colleen Weber is a fee-only financial advisor, CERTIFIED FINANCIAL PLANNER® professional, and CPA based in Chanhassen, Minnesota. With more than 20 years of financial planning experience, Colleen provides comprehensive financial planning and wealth management. She specializes in serving clients nearing retirement, retirees, busy professionals, and women. She is passionate about developing financial plans that save clients on taxes and investment strategies that help them pursue their goals. Learn more about Colleen by connecting with her on LinkedIn or booking a complimentary phone call meeting.