Rapid7 (RPD) RSU sell-vs-hold
Calculator · free · no signup · RPDSell at vest or hold? Compare after-tax payout from selling Rapid7 RSUs at vest vs. holding through the LTCG cliff at 12 months.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your vest
Tax inputs
Hold strategy
Best after-tax payout — at year 1 yr
$47,709
Sell + invest wins by $4,981 over Hold 1 yr.
Estimates only. Not financial advice.
Heads-up: under-withholding. Your employer withholds federal tax at the IRS supplemental rate (22.0% on this vest, ≈ $17,600). Your marginal federal rate on this vest is 32.7%, owing $26,171. Expect to settle the $8,571 gap at tax time.
The hidden purchase
Tax was paid at vest either way. Holding is mathematically equivalent to taking $44,509 in after-tax cash and buying $44,509 of RPD today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in RPD. Holding past one year converts the gain to LTCG.
Sell + invest
Best payout| Vest value (shares × price) | $80,000 |
| Federal | |
| State | |
| Medicare | −$1,160 |
| Additional Medicare | −$720 |
| Market gain over 1 yr at 10.0% | $4,451 |
| Cap-gain tax on diversified gain — LTCG (federal + state + NIIT) | −$1,251 |
| Net at year 1 yr | $47,709 |
Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Hold 1 yr
| Vest value (shares × price) | $80,000 |
| Vest tax (federal + state + FICA) | |
| Net at year 1 yr | $42,728 |
Sold 444 shares to cover vest tax (net-settled); kept 556 shares 1 yr to qualify for long-term capital gains.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.
Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.
Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.
You evaluated one RSU vest. The beta plans every vest of every grant across years, with concentration and AMT in the loop.
Request beta access →Related calculators: RSU Lot Order Calculator · Stock Concentration Calculator
About Rapid7
Rapid7 (RPD) is a public Cybersecurity company, incorporated in Delaware and headquartered in Boston, MA.
Equity grants at Rapid7 typically include restricted stock units (RSUs).
The Metasploit Project is a computer security project that provides information about security vulnerabilities and aids in penetration testing and IDS signature development. It is owned by Rapid7, a Boston, Massachusetts-based security company.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 2000 and headquartered in Boston, the company built vulnerability management around InsightVM and then expanded into detection and response, cloud security, and application testing. It also stewards Metasploit, the penetration testing framework acquired in 2009, which gives it unusual standing with practitioners who use the open source edition daily. The strategy has been platform consolidation for mid-market security teams that cannot staff separate tools, and the company competes with Tenable and Qualys on vulnerability coverage.
Sources: rapid7.com · en.wikipedia.org
Equity comp at Rapid7
- 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 Rapid7.
Rapid7 (RPD) RSUs vest as ordinary income at the price on vest day. The decision is whether to sell at vest and reinvest, or hold the shares through the 12-month LTCG cliff. This calculator runs both paths through the same after-tax math so you can compare like-for-like.
All Rapid7 tools → · Use the generic RSU Sell-vs-Hold Calculator for any company. Diversifying multiple RSU lots? See the lot-by-lot sell order →
Rapid7 equity questions
- Should I sell or hold my Rapid7 RSUs at vest?
- Rapid7 restricted stock units (RSUs) are taxed as ordinary income on their value at vest whether or not you sell. The only open decision is what to do with the shares afterward: sell at vest and reinvest, or hold past twelve months for long-term capital-gains treatment on any further gain. The calculator above runs both paths through the same after-tax math so you can compare them directly.
- Does Rapid7 grant ISOs, NSOs, or RSUs?
- Equity compensation at Rapid7 typically takes the form of restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Do Rapid7 RSUs use double-trigger vesting?
- No. Rapid7 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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