Plan your Glean NSO exercise
Calculator · free · no signup · pre-IPOGlean 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
$143,002
Hold 1 yr wins by $42,042 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $173,150 |
| Federal | |
| State | |
| Medicare | −$2,511 |
| Additional Medicare | −$1,558 |
| Market gain over 1 yr at 10.0% | $9,419 |
| LTCG on diversified gain (fed + state + NIIT) | −$2,647 |
| Net at year 1 | $100,960 |
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) | −$19,078 |
| Net at year 1 | $143,002 |
Sold 2,890 shares at exercise to cover strike + tax; 2,110 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 Glean
Glean is a privately held AI company, headquartered in Palo Alto, CA.
Last reported secondary-market price: $44.63 per share (as of 2026-06-16). Your own 409A may differ.
$7.2B; enterprise AI search.
Equity grants at Glean typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Glean builds an enterprise AI search and work platform that indexes across a company's internal SaaS tools (Slack, Salesforce, Google Drive, and 100+ others), surfacing relevant information through a natural-language interface. Arvind Jain, previously a Distinguished Engineer at Google and co-founder of Rubrik, launched the company in 2019 alongside T.R. Vishwanath, Piyush Prahladka, and Tony Gentilcore. Glean crossed $100 million in annual recurring revenue in 2025 and raised $150 million in a Series F at a $7.2 billion valuation in February 2026, bringing total funding to $765 million.
Sources: glean.com · research.contrary.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Glean.
Glean 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 Glean's last reported price of $44.63, exercising 5,000 NSOs with a $13.39 strike creates a $156,200 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $42,174 and $70,290 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 Glean tools → · Use the generic NSO Exercise Calculator for any company.
Glean equity questions
- How is a Glean 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 Glean grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Glean grant ISOs, NSOs, or RSUs?
- Equity compensation at Glean 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 Glean 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 Glean 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 Glean equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.