BILL Holdings (BILL) RSU sell-vs-hold
Calculator · free · no signup · BILLSell at vest or hold? Compare after-tax payout from selling BILL Holdings RSUs at vest vs. holding through the LTCG cliff at 12 months.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your vest
Tax inputs
Hold strategy
@ 20.0% / yr
Best after-tax payout — at year 1 yr
$47,823
Sell + invest wins by $4,992 over Hold 1 yr.
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 BILL 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.
About BILL Holdings
BILL Holdings (BILL) is a public Fintech company. IPO'd Dec 12, 2019.
Last close: $38.32 per share (as of 2026-05-06).
Equity grants at BILL Holdings typically include non-qualified stock options (NSOs) and restricted stock units (RSUs).
René Lacerte, whose grandfather founded Lacerte Software (later acquired by Intuit), started BILL in April 2006 in San Jose to automate accounts payable and receivable workflows for the small and mid-size businesses he had watched struggle with paper checks and manual approvals. The platform integrates with accounting software to digitize invoice ingestion, approval routing, and payment execution across ACH, check, card, and international wire, processing more than $300 billion in payment volume annually. BILL IPO'd on NYSE in December 2019 and reported $1.27 billion in revenue in fiscal year 2024.
Sources: en.wikipedia.org · fintechleaders.substack.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by BILL Holdings.
BILL Holdings (BILL) is a public Fintech company. IPO'd Dec 12, 2019. 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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