SailPoint (SAIL) NSO Exercise Calculator
Calculator · free · no signup · SAILPlan your SailPoint 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
Best after-tax payout — at year 1
$199,080
Sell + invest wins by $20,783 over Hold 1 yr.
Estimates only. Not financial advice.
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% | $18,573 |
| LTCG on diversified gain (fed + state + NIIT) | −$5,219 |
| Net at year 1 | $199,080 |
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 | $178,297 |
Sold 2,678 shares at exercise to cover strike + tax; 2,322 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.
You calculated one NSO decision. The beta plans NSOs alongside RSUs and ISOs in a single multi-year tax plan.
Request beta access →About SailPoint
SailPoint (SAIL) is a public Cybersecurity company, incorporated in Delaware and headquartered in Austin, TX. IPO'd Feb 13, 2025.
Last close: $14.21 per share (as of 2026-06-16).
Identity security; PE relisting.
Equity grants at SailPoint typically include incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs).
Identity governance software, which controls who at an enterprise can access which systems and data, is SailPoint's core product since Mark McClain and Kevin Cunningham founded the company in Austin, Texas in 2005. SailPoint listed on Nasdaq in 2017, was taken private by Thoma Bravo in a $6.9 billion buyout in 2022, and returned to Nasdaq as SAIL in February 2025, raising $1.38 billion at $23 per share. Annual recurring revenue crossed $875 million at IPO and reached $1.35 billion by early 2026, growing roughly 30% year-over-year.
Sources: bloomberg.com · investor.sailpoint.com
Equity comp at SailPoint
- RSUs use single-trigger vesting: shares become yours as each portion vests on schedule, and the value is taxed as ordinary income at that point. No IPO or acquisition is required.
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by SailPoint.
Use this calculator to estimate your SailPoint (SAIL) 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.
Example: at SailPoint (SAIL)'s last close of $14.21, exercising 5,000 NSOs with a $4.26 strike creates a $49,750 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $13,433 and $22,388 depending on your bracket and state. The calculator above computes the exact figure for your situation and compares selling now vs. holding through the long-term capital-gains threshold.
All SailPoint tools → · Use the generic NSO Exercise Calculator for any company.
SailPoint equity questions
- How is a SailPoint NSO exercise taxed?
- Exercising a non-qualified stock option (NSO) creates ordinary income on the bargain element (the price on the day you exercise minus your strike), subject to federal income tax, state income tax, and FICA. The calculator above computes that tax for your SailPoint grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does SailPoint grant ISOs, NSOs, or RSUs?
- Equity compensation at SailPoint typically takes the form of incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs). Incentive stock options can trigger the alternative minimum tax (AMT) when you exercise. Restricted stock units are taxed as ordinary income when they vest.
- When did the SailPoint IPO lockup expire?
- SailPoint (SAIL) went public on February 13, 2025. The standard post-IPO lockup runs 180 days, so employee and insider shares generally became sellable around August 12, 2025. Confirm against your own grant paperwork, since some lockups release early or in stages.
- Do SailPoint RSUs use double-trigger vesting?
- No. SailPoint restricted stock units (RSUs) use single-trigger vesting: each tranche becomes yours as it vests on schedule, taxed as ordinary income at that point, with no liquidity event required.
One piece of the puzzle.
OptionsAhoy plans your SailPoint equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.