Sell Progressive (PGR) stock to fund a goal
Calculator · free · no signup · PGRNeed cash for a goal? Plan the minimum-tax schedule to sell your vested Progressive (PGR) shares and net a target amount by a target date, across tax years.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
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 | $109,597 | $111,639 | $111,883 | $118,769 |
| Wealth @ target | $719,068 | $716,894 | $714,464 | $712,031 |
| Chance of shortfall | <0.1% | 0% | 1.9% | 3.4% |
Feasible
$400,071 net by 08/01/27
Total tax: $109,597 (federal $58,819, state $36,048, NIIT $14,729)
Schedule · Recommended
| Sale date | Shares | Tax | Net | Cumulative |
|---|---|---|---|---|
| 08/17/26 | 4,085 | $351,104 | $360,043 | |
| 03/31/27 | 4 | $360 | $360,406 | |
| 04/30/27 | 32 | $2,896 | $363,321 | |
| 05/31/27 | 100 | $9,103 | $372,466 | |
| 06/30/27 | 100 | $9,157 | $381,644 | |
| 07/31/27 | 100 | $9,212 | $390,857 | |
| 08/01/27 | 100 | $9,215 | $400,071 |
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 3,479 shares worth $411,873 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 Progressive
Progressive (PGR) is a public Fintech company, incorporated in Ohio and headquartered in Mayfield Village, OH.
Equity grants at Progressive typically include restricted stock units (RSUs).
The Progressive Corporation is an American insurance company headquartered in Mayfield, Ohio. It was co-founded in 1937 by Jack Green and Joseph M. Lewis. The company insures passenger vehicles, motorcycles, recreational vehicles (RVs), trailers, boats, personal water craft (PWC), and commercial vehicles. Progressive also provides home, life, pet, and other types of insurance through select companies.
Source: Wikipedia (CC BY-SA 4.0)
Joseph Lewis and Jack Green founded the company in 1937 and built it by insuring drivers other carriers rejected, then by publishing competitors' rates alongside its own, an unusual transparency bet. Snapshot telematics extended the underwriting edge by pricing on observed driving behavior. Direct sales through advertising, personified by the Flo character, run alongside independent agents. Auto insurance profitability swings with claim severity, which inflation in vehicle repair costs and used car prices pushed sharply after 2021. Headquarters are in Mayfield Village, Ohio.
Sources: progressive.com · en.wikipedia.org
Equity comp at Progressive
- RSUs use single-trigger vesting: shares become yours as each portion vests on schedule, and the value is taxed as ordinary income at that point. No IPO or acquisition is required.
Researched 2026-08-17.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Progressive.
If you hold vested Progressive (PGR) 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 Progressive tools → · Use the generic Stock Sale Funding Calculator for any company.
Progressive equity questions
- How much PGR 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 PGR 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 Progressive grant ISOs, NSOs, or RSUs?
- Equity compensation at Progressive typically takes the form of restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Do Progressive RSUs use double-trigger vesting?
- No. Progressive restricted stock units (RSUs) use single-trigger vesting: each tranche becomes yours as it vests on schedule, taxed as ordinary income at that point, with no liquidity event required.
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OptionsAhoy plans your Progressive equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.