Sell Guidewire Software, Inc. (GWRE) stock to fund a goal
Calculator · free · no signup · GWRENeed cash for a goal? Plan the minimum-tax schedule to sell your vested Guidewire Software, Inc. (GWRE) shares and net a target amount by a target date, across tax years.
AlphaLatitude Inc. · Free ToolsOur tools respect your browsing privacy. Independently verified:
Inputs
Your equity
One stack per ticker (current-employer RSUs, prior-employer holdings, index fund, etc.). Each stack has its own current price, growth assumption, and cost-basis lots.
Drives chance-of-shortfall · default 30%
Lots
Plan
Estimates only. Not financial advice.
Lock-in-now is deterministic (0%). Plans that wait depend on future prices; risk is near-zero when inventory comfortably exceeds the goal. Volatility: each stack's option-implied vol if a ticker is set, otherwise 30%. Lognormal model; real markets have fatter tails.
| Tax | $109,654 | $111,723 | $111,788 | $118,699 |
| Wealth @ target | $718,258 | $716,076 | $713,344 | $710,913 |
| Chance of shortfall | <0.1% | 0% | 1.7% | 3.3% |
Feasible
$400,027 net by 08/01/27
Total tax: $109,654 (federal $58,856, state $36,063, NIIT $14,736)
Schedule · Recommended
| Sale date | Shares | Tax | Net | Cumulative |
|---|---|---|---|---|
| 08/26/26 | 4,088 | $351,349 | $360,067 | |
| 03/31/27 | 4 | $359 | $360,430 | |
| 04/30/27 | 32 | $2,891 | $363,340 | |
| 05/31/27 | 100 | $9,088 | $372,468 | |
| 06/30/27 | 100 | $9,141 | $381,631 | |
| 07/31/27 | 100 | $9,196 | $390,828 | |
| 08/01/27 | 100 | $9,199 | $400,027 |
Risk vs wealth
Each dot is a possible plan. Right is riskier, up is more wealth left over.
Trajectory of cash netted
Solid line = expected. Shaded band = 10th–90th percentile under price uncertainty.
After the plan
You keep 3,476 shares worth $410,758 at the projected target-date price, invested for the next decision.
You solved for a cash target. The beta optimizes your full portfolio across multiple goals and market scenarios, not just one funding need.
Request beta access →Related calculators: RSU Lot Order Calculator · Stock Concentration Calculator · RSU Sell-vs-Hold Calculator
About Guidewire Software, Inc.
Guidewire Software, Inc. (GWRE) is a public Cloud/SaaS company.
Added by ETL (market cap $12.6B).
Equity grants at Guidewire Software, Inc. typically include incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs).
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Guidewire Software, Inc..
If you hold vested Guidewire Software, Inc. (GWRE) shares and need a set amount of cash by a date (a house down payment, tuition, a sabbatical, a business buy-in), the question is which lots to sell and in which tax years to keep the most after tax. This calculator builds the minimum-tax sell schedule across your lots, accounting for federal long-term capital gains, the net investment income tax, and your state.
All Guidewire Software, Inc. tools → · Use the generic Stock Sale Funding Calculator for any company.
Guidewire Software, Inc. equity questions
- How much GWRE stock do I sell to fund a goal without overpaying tax?
- It depends on your cost basis, your target amount and date, and how the sale spreads across tax years. Selling vested GWRE shares triggers long-term capital-gains tax, plus the 3.8% net investment income tax and state tax above certain income, and bunching a large sale into one year can push the gain into a higher bracket. The calculator above builds the minimum-tax sell schedule across your lots to net your target amount by your date.
- Does Guidewire Software, Inc. grant ISOs, NSOs, or RSUs?
- Equity compensation at Guidewire Software, Inc. 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.
One piece of the puzzle.
OptionsAhoy plans your Guidewire Software, Inc. equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.