3 Ways to Help C-Suite Clients With Retirement

Commentary January 12, 2024 at 02:24 PM
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Founders of public companies and corporate executives are passionate about their jobs. Even as retirement age nears, they may not be thinking about slowing down.

We engage with highly successful clients in their 70s and 80s who are still very active with their companies, because they love what they do — it's who they are.

But a corporate action, health event, new direction for the company or any number of circumstances can bring retirement quickly into focus, so they need to be prepared.

It's our job to make sure our C-suite clients have plans in place for transitioning to a life in which they no longer have their executive-pay cash flow.

Beyond the typical deferred compensation and Social Security payouts, here are three considerations to keep in mind as you strive to guide them toward a rewarding and well-funded retirement:

Converting Equity Compensation

Executives' cash compensation grows throughout their careers.

Real wealth creation generally comes from the equity component of their compensation packages — most often through restricted awards, performance awards or compensatory stock options: non-qualified and incentive stock options.

The cash component of executives' compensation typically serves to support their lifestyles — new boats, vacation homes, golf club memberships.

After retirement, they intend to maintain that lifestyle, so throughout their career, executives may need to focus on converting their equity compensation into a diverse and income-producing portfolio to preserve that wealth and to generate a level of cash flow commensurate with the cash component of their working years.

Planning a Concentration Strategy

Five to 10 years before clients retire, you'll want to start having conversations around how much equity they can afford to hold in their company. These are delicate — and sometimes difficult — discussions.

Many founders and executives are very confident about the future of their companies. Or they are sensitive to the market perception of reductions they make in their concentration of company stock.

Of course, stocks don't always move in the right direction and there are ways to methodically reduce concentration so that investors feel the executives' continued alignment with the company. The focus needs to be on managing risk.

Things will look very different for an executive at a small, fast-growing company that doesn't have any earnings compared to an executive at a larger company in a conservative industry that doesn't see a lot of change. Corporate culture can also play a role in a client's approach to equity concentration.

Another consideration is risk tolerance. Clients with a large balance sheet can afford to run a much higher percentage of their company's equity as a percentage of their overall portfolio than those with a more modest portfolio.

Deciding When to Sell

A client's disposition strategy may be time-based, with a plan to take equity off the table periodically. More likely, that strategy will be driven by the company valuation.

Either way, or a combination of both strategies, may be appropriate, but it's helpful to determine which method will be used so it can be incorporated into the financial plan.

If clients are the beneficiary of restricted stock awards or performance stock awards, it's common to sell those shares at vest because they've already been taxed in line with other W-2 income.

But if you're talking about low-basis stock held in a brokerage account for 20 years, there might be a significant tax burden to selling.

Say a client's company has an acquisition on the horizon that's not yet public, and because the client has knowledge of it, the executive can't trade.

A Rule 10b5-1 sales plan is designed to allow executives with knowledge of highly sensitive non-public information to trade throughout the year. These plans are especially useful during periods when C-suite executives are restricted from trading company stock, referred to as "blackout periods."

These periods generally coincide with the timing of the company's quarterly earnings schedule or when a material event has occurred.

The company's stock may be most volatile during this period, and the 10b5-1 plan allows clients to set predetermined parameters for sale of the stock months ahead of the sale event. The plan provides the flexibility to trade the stock at an aspirational or attractive valuation during a period when the executive would have otherwise been restricted.

Depending on a client's industry, the executive may be subject to blackout most of the year with only a few, short, open periods throughout the year, or the blackouts may be limited to four to eight weeks each quarter during the company's earnings period.

However you advise your C-suite clients, you'll want to be sure to include their accountants and corporate counsel in the conversation. Together, you can help them maximize the wealth they worked so hard to build.


Sam Aspinwall is a private wealth advisor, managing director and founder of Executive Consulting of Raymond James, an advisory practice focused on serving public company corporate executives. 

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