Plan your Grammarly ISO exercise
Calculator · free · no signup · pre-IPOGrammarly is pre-IPO. Plan your AMT impact at any valuation: current 409A, expected IPO price, or post-IPO scenarios.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Seeded from secondary-market data, as of Jun 9, 2026
Tax inputs
Grant timeline
Net final value at year 3 sale — optimized plan
$75,284
After-tax dollars at end of year 3, net of all federal + state taxes through the sale.
This year: exercise 3,334 shares (of 10,000 total).
= gross gain at sale − federal + state LTCG − AMT premium above baseline regular tax (time-valued)
AMT premium for exercising: $0 (on top of $228,434 regular tax across the horizon)
Optimized plan keeps $503 more than lump-sum.
Federal AMT crossover this year: 6,128 shares ($57,238 bargain element). Above that, each additional share this year adds federal AMT.
Estimates only. Not financial advice.
Net final value by year
Running tally: NTV from shares exercised through year y, minus AMT premium paid through year y. The last year matches the plan's headline NTV. Hover a year for plan totals.
Optimized exercise schedule
You pay the higher of Regular tax and Tentative AMT per jurisdiction, then subtract Credit recovered. The result is Net tax. Hover any number for the bracket-by-bracket breakdown.
| 1No AMT | 3,334 | |||
| 2No AMT | 3,333 | |||
| 3No AMT | 3,333 |
Federal AMT credit
Earned
$0
Recovered
$0
Remaining
$0
Plan comparison
Net value at the end of your hold horizon.
Lump-sum
All in Year 1
$74,781
−$503
Even split
Equal shares each year
$75,284
Optimized
Tax-aware schedule
$75,284
Highest
Estimates only. Excludes disqualifying dispositions, NSOs, multi-state moves, and AMT preferences other than ISO bargain elements. Long-term capital gains tax assumes a qualifying disposition (ISO held ≥1 yr from exercise and ≥2 yr from grant); state LTCG follows ordinary brackets except where the state grants preferential treatment (HI, ND, SC, WI, AR, NM) or has a dedicated LTCG-only tax (WA). Assumes you are within the $100K ISO limit (any portion of an annual ISO grant whose FMV at grant exceeds $100K is treated as NSO from the start, §422(d)). State AMT figures are 2025 (next-year values published in late 2026). Not financial advice.
QSBS note. If your shares qualify (typically pre-IPO C-corp grants held 5+ years), a federal rule lets you exclude up to $10M of gain on a future sale from federal tax. That single rule shifts exercise-timing math more than AMT does. (This is §1202 “qualified small-business stock”.) Modeled in beta, not here.
You optimized one grant in isolation. The beta optimizes ISOs alongside your RSUs, NSOs, and stock in one 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.
The calculator works at any Grammarly valuation: enter your strike, the current 409A FMV, an expected IPO price, or anywhere in between. AMT is triggered on the bargain element (FMV minus strike) when you exercise; the calculator models federal AMT, state AMT, and the multi-year credit-recovery path.
Example: at Grammarly's last reported price of $14.34, exercising 5,000 ISOs with a $4.3 strike creates a $50,200 bargain element. Above the 2026 federal AMT exemption ($88,100 single, $137,000 married joint), the 28% AMT rate adds roughly $14,056 on top of regular tax before any state AMT (CA, CO, CT, MN). The credit recovers in later years when your regular tax exceeds AMT. The calculator above runs your exact figures.
All Grammarly tools → · Use the generic AMT + ISO Exercise Calculator for any company.
Grammarly equity questions
- How much alternative minimum tax (AMT) will I owe exercising Grammarly ISOs?
- Exercising incentive stock options (ISOs) does not create regular income tax, but the bargain element (the fair market value at exercise minus your strike price) counts toward the alternative minimum tax (AMT). The amount depends on the bargain element, your other income, your filing status, and your state. The calculator above models federal and state AMT, the AMT crossover point, and how the credit recovers in later years for your exact Grammarly figures.
- 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.