BILL Holdings (BILL) NSO Exercise Calculator
Calculator · free · no signup · BILLPlan your BILL Holdings NSO exercise — federal, state, FICA — and compare sell-vs-hold for long-term capital gains.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Tax inputs
Hold strategy
@ 20.0% / yr
Best after-tax payout — at year 1
$199,194
Sell + invest wins by $20,795 over Hold 1 yr.
Sell + invest
Best payout| Bargain element (sale − strike) | $350,000 |
| Federal | |
| State | |
| Medicare | −$5,075 |
| Additional Medicare | −$3,150 |
| Market gain over 1 yr at 10.0% | $18,583 |
| LTCG on diversified gain (fed + state + NIIT) | −$5,222 |
| Net at year 1 | $199,194 |
Sell every share immediately; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Exercise + hold 1 yr
| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | $0 |
| Net at year 1 | $178,399 |
Sold 2,677 shares at exercise to cover strike + tax; 2,323 shares held 1 yr for LTCG.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're exercising as a current employee.
Both columns are stated in year-1 dollars: sell-now proceeds compound at the market return and pay LTCG on the gain at year 1; any cash paid out of pocket on the hold side carries the same opportunity cost.
Net at year N — by hold period
Estimates only. Excludes AMT (NSOs do not trigger AMT), state-AMT, multi-state moves, and disqualifying-disposition edge cases. 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. Use this calculator to estimate your NSO exercise tax (federal, state, FICA), then compare selling now versus holding through the long-term capital gains threshold. Inputs are yours — grant terms, current price, your income, your state.
All BILL Holdings tools → · Use the generic NSO Exercise Calculator for any company.
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