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Tuesday, September 22, 2026

Part III: What Primary Mitigation Strategies Exist for Companies with ... - Goodwin Procter

This alert is the third in a three-part Goodwin series regarding double-vest restricted stock unit awards (Double-Vest RSUs). As discussed in Part I and Part II of our series, many mature start-up and other high value pre-IPO companies have shifted away from granting stock options to awarding Double-Vest RSUs. Many of those same companies may be navigating challenging waters at this time or in the near future because Double-Vest RSUs potentially are approaching the end of their term/expiration date without a liquidity event on the horizon.

A critical concept that we covered in Part II (that is a baseline issue to be mindful of in this Part III) is that if a Liquidity Event 1 does not occur prior to the term/expiration date of a Double-Vest RSU, the Double-Vest RSU must be forfeited because the term/expiration date likely cannot be extended under U.S. federal tax laws.

With that foundational baseline established, Part III of our series suggests some primary mitigation strategies for companies to consider to prevent grantees from forfeiting their Double-Vest RSUs. None of these mitigation strategies are a perfect “one size fits all” solution to this problem, and a strategy that is workable for one company may not be a great fit for another. As explained in greater detail below, most of the proposed strategies will likely require significant advance planning as they will involve delicate employee communications, potential cash outlays, and/or support from investors and...



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