Plan your Rippling NSO exercise
Calculator · free · no signup · pre-IPORippling is pre-IPO. Plan your NSO exercise tax (federal, state, FICA) at any expected valuation.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Seeded from secondary-market data, as of Jun 16, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$148,550
Hold 1 yr wins by $35,694 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $194,350 |
| Federal | |
| State | |
| Medicare | −$2,818 |
| Additional Medicare | −$1,749 |
| Market gain over 1 yr at 10.0% | $10,529 |
| LTCG on diversified gain (fed + state + NIIT) | −$2,959 |
| Net at year 1 | $112,856 |
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
Best payout| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | −$16,908 |
| Net at year 1 | $148,550 |
Sold 2,846 shares at exercise to cover strike + tax; 2,154 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 Rippling
Rippling is a privately held Cloud/SaaS company, incorporated in Delaware and headquartered in San Francisco, CA.
Last reported secondary-market price: $48.87 per share (as of 2026-06-16). Your own 409A may differ.
HR/IT platform.
Equity grants at Rippling typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Rippling is a privately owned international software company. Launched in 2017 in San Francisco, California, it operates a cloud-based software platform that allows businesses to manage their HR, finances, and IT matters.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 2016 by Parker Conrad (returning after his Zenefits ouster) and Prasanna Sankar, Rippling consolidates HR, IT, and finance onto one employee record, handling payroll, benefits, device management, expenses, and corporate cards. The San Francisco company closed a $450M Series G in May 2025 at a $16.8B valuation, with Conrad publicly deferring an IPO until profitability tightens. Headlines through 2025 and into 2026 have centered on its civil RICO and trade-secret suit against Deel, alleging a cultivated insider funneled competitive intelligence; a federal judge cleared the case toward California trial in February 2026.
Sources: cnbc.com · rippling.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Rippling.
Rippling NSO exercise creates ordinary income on the bargain element (federal, state, and FICA) at the price on the day you exercise. The calculator works at any valuation, so you can model your exercise cost at the current 409A FMV, an expected IPO price, or post-IPO scenarios.
Example: at Rippling's last reported price of $48.87, exercising 5,000 NSOs with a $14.66 strike creates a $171,050 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $46,183 and $76,972 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 Rippling tools → · Use the generic NSO Exercise Calculator for any company.
Rippling equity questions
- How is a Rippling 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 Rippling grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Rippling grant ISOs, NSOs, or RSUs?
- Equity compensation at Rippling typically takes the form of incentive stock options (ISOs) and non-qualified stock options (NSOs). Incentive stock options can trigger the alternative minimum tax (AMT) when you exercise.
- Are Rippling shares eligible for QSBS?
- They might be. Qualified small business stock (QSBS) under Internal Revenue Code Section 1202 can exclude federal tax on much of the gain when shares were acquired at original issuance from a C-corporation while its gross assets were under $50 million, and held at least five years. Whether your Rippling shares qualify turns on when you acquired them and the company's asset size at that time.
One piece of the puzzle.
OptionsAhoy plans your Rippling equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.