Plan your Sierra NSO exercise
Calculator · free · no signup · pre-IPOSierra 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 Jul 31, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$168,062
Hold 1 yr wins by $5,640 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $283,400 |
| Federal | |
| State | |
| Medicare | −$4,109 |
| Additional Medicare | −$2,551 |
| Market gain over 1 yr at 10.0% | $15,153 |
| LTCG on diversified gain (fed + state + NIIT) | −$4,258 |
| Net at year 1 | $162,422 |
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) | −$6,462 |
| Net at year 1 | $168,062 |
Sold 2,728 shares at exercise to cover strike + tax; 2,272 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 →Related calculators: Stock Concentration Calculator · Multi-Year ISO Exercise Schedule Calculator
About Sierra
Sierra is a privately held AI company, headquartered in San Francisco, CA.
Last reported secondary-market price: $66.68 per share (as of 2026-07-31). Your own 409A may differ.
CX agents; Bret Taylor.
Equity grants at Sierra typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
In 2023, Bret Taylor (former Salesforce co-CEO and Twitter board chair) and Clay Bavor (who led Google Labs) co-founded Sierra to build AI agents that handle customer conversations for enterprises, replacing traditional contact-center workflows with software that can reason, take actions, and escalate contextually. Sierra reached $100 million in annual recurring revenue before the end of 2025. It raised $175 million in October 2024 at a $4.5 billion valuation, $350 million in September 2025 at $10 billion, and $950 million in May 2026 at $15.8 billion.
Sources: techcrunch.com · cnbc.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Sierra.
Sierra 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 Sierra's last reported price of $66.68, exercising 5,000 NSOs with a $20 strike creates a $233,400 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $63,018 and $105,030 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 Sierra tools → · Use the generic NSO Exercise Calculator for any company.
Sierra equity questions
- How is a Sierra 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 Sierra grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Sierra grant ISOs, NSOs, or RSUs?
- Equity compensation at Sierra 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 Sierra 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 Sierra 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 Sierra equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.