Plan your Grammarly NSO exercise
Calculator · free · no signup · pre-IPOGrammarly 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 9, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$51,109
Hold 1 yr wins by $37,850 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $21,700 |
| Federal | |
| State | |
| Medicare | −$315 |
| Additional Medicare | −$195 |
| Market gain over 1 yr at 10.0% | $1,237 |
| LTCG on diversified gain (fed + state + NIIT) | −$348 |
| Net at year 1 | $13,259 |
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) | −$15,140 |
| Net at year 1 | $51,109 |
Sold 4,137 shares at exercise to cover strike + tax; 863 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 Grammarly
Grammarly is a privately held Cloud/SaaS company, headquartered in San Francisco, CA.
Last reported secondary-market price: $14.34 per share (as of 2026-06-09). Your own 409A may differ.
AI writing.
Equity grants at Grammarly typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Grammarly is an American English-language writing assistant software tool. It started as a tool to review the spelling, grammar, and tone of a piece of writing and to identify possible instances of plagiarism. Since 2025 it has integrated extensive generative AI tools, including options to generate essays from scratch, to suggest and insert citations, to "humanize" the text to avoid it being flagged as AI-generated, and to predict grades based on user input on the instructor, course, and university. It can also make stylistic and tonal recommendations. An "Expert review" feature, which attributed Grammarly's editing suggestions to subject-matter experts in various fields, was discontinued in March 2026 due to criticism and complaints.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 2009 by Ukrainian engineers Max Lytvyn, Alex Shevchenko, and Dmytro Lider, the company began as a browser extension catching typos and grew into a writing assistant used by roughly 40 million people. December 2024 brought the $400M+ Coda acquisition, installing Coda co-founder Shishir Mehrotra as CEO and reframing the roadmap around AI-native productivity. By late 2025 the parent had absorbed email client Superhuman, rebranded under that name, and shipped a unified suite spanning writing, docs, inbox, and a proactive agent layer called Go.
Sources: grammarly.com · techcrunch.com · techcrunch.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Grammarly.
Grammarly 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 Grammarly's last reported price of $14.34, exercising 5,000 NSOs with a $4.3 strike creates a $50,200 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $13,554 and $22,590 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 Grammarly tools → · Use the generic NSO Exercise Calculator for any company.
Grammarly equity questions
- How is a Grammarly 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 Grammarly grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Grammarly grant ISOs, NSOs, or RSUs?
- Equity compensation at Grammarly 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 Grammarly 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 Grammarly 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 Grammarly equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.