DocuSign (DOCU) RSU sell-vs-hold

Calculator · free · no signup · DOCU

Sell at vest or hold? Compare after-tax payout from selling DocuSign RSUs at vest vs. holding through the LTCG cliff at 12 months.

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Your vest

pre-IPO? enter price manually

Tax inputs

Hold strategy

1 yr
20%
10.0%

Best after-tax payout — at year 1 yr

$47,823

Sell + invest wins by $4,992 over Hold 1 yr.

This vest pushes your top federal rate from 24% to 35%. Hover the Federal value below for the bracket-by-bracket slicing.

Sell + invest

Best payout
Vest value (shares × price)$80,000
Federal
State
Medicare−$1,160
Additional Medicare−$720
Market gain over 1 yr at 10.0%$4,462
Cap-gain tax on diversified gain — LTCG (federal + state + NIIT)−$1,254
Net at year 1 yr$47,823

Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.

Hold 1 yr

Vest value (shares × price)$80,000
Vest tax (federal + state + FICA)
Net at year 1 yr$42,830

Sold 442 shares to cover vest tax (net-settled); kept 558 shares 1 yr to qualify for long-term capital gains.

Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.

Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.

The hidden purchase

Tax was paid at vest either way. Holding is mathematically equivalent to taking $44,615 in cash and buying $44,615 of DOCU today.

Would you voluntarily put that much of your bonus into a single position? If not, sell-at-vest is the rational default — and diversifying captures most of the long-run return without the single-stock variance.

Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.

DocuSign (DOCU) is a public Cloud/SaaS company. DocuSign IPO'd on 2018-04-27. RSUs vest as ordinary income at the price on vest day. The decision is whether to sell at vest and reinvest, or hold the shares through the 12-month LTCG cliff. This calculator runs both paths through the same after-tax math so you can compare like-for-like.

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