Many SAP employees arrive with a clear goal: reduce their concentration in SAP stock. The challenge is building a plan that does it in the right order, across the right time horizon, with the least tax friction. Henry Supinski, a former SAP VP, has helped clients do exactly that.
Before selling anything, you need a clear view of your entire SAP position: the cost basis of every lot of shares (RSU grants, ESPP purchases, and any shares bought on the open market), the holding period of each lot, and how each lot's gain will be taxed. Shares held less than a year are taxed as ordinary income on sale. Shares held more than a year qualify for long-term capital gains rates, which are meaningfully lower for most high earners.
Most employees do not have this organized. Building it is the first step.
If you give to charity, donating appreciated SAP shares directly to a donor-advised fund is significantly more efficient than selling shares and donating cash. You get a deduction for the full market value and never pay capital gains on the appreciation. Over a multi-year diversification plan, this can eliminate a meaningful amount of tax on shares you would have sold anyway.
Tax efficiency is important, but it is not the only consideration. If your SAP concentration is very high relative to your overall wealth, the risk of staying concentrated may outweigh the cost of paying more tax to diversify faster. We model both scenarios explicitly so you can make an informed decision about the trade-off.
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Start with the lots that have the highest cost basis and the lowest embedded gain. These minimize the tax cost of early sales. Then work through lower-basis lots systematically across subsequent tax years, targeting an annual gain amount that keeps you in a manageable effective tax rate.
For most employees with meaningful concentration, a two to four year plan is common. The right timeline depends on the size of the position relative to your overall wealth, your income in each year, your charitable goals, and your risk tolerance for staying concentrated. A shorter plan means more tax each year. A longer plan preserves optionality but extends the concentration risk.
If you give to charity regularly, yes. Donating appreciated SAP shares to a donor-advised fund lets you take a full deduction at market value, avoid the embedded capital gains tax, and grant to your chosen charities over time. It is one of the most efficient tools available for employees with both a large position and charitable intent.
A price drop reduces the tax cost of selling remaining shares and can actually accelerate your plan at lower total tax cost. It also validates the reason for diversifying. The goal of the plan is to reduce concentration risk, and a price drop is exactly that risk materializing.
We are fee-only and fiduciary. We are paid only by our clients, never by commissions on trades or transactions. Our only incentive is to help you make the right decisions with your equity.