AMT + ISO Exercise Calculator
Open →Plan Sierra ISO exercise around the AMT bargain element. Federal + state, AMT crossover, multi-year credit recovery.
Deep dive: Four AMT mistakes you can still fix before December 31 →Sierra is pre-IPO. Plan your AMT and NSO exercise tax at any valuation: current 409A FMV, expected IPO price, or post-IPO scenarios.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Plan Sierra ISO exercise around the AMT bargain element. Federal + state, AMT crossover, multi-year credit recovery.
Deep dive: Four AMT mistakes you can still fix before December 31 →Left Sierra with vested ISOs? Model the 90-day exercise-or-forfeit window: your deadline, AMT cost of exercising at once, and the share count that maximizes after-tax value.
Sierra NSO exercise tax (federal, state, FICA) plus a sell-vs-hold comparison for long-term capital gains.
Deep dive: Six NSO mistakes your tax advisor probably won't mention →Don't work at Sierra? Find another company.
Sierra is a privately held AI company, headquartered in San Francisco, CA.
CX agents; Bret Taylor.
Equity grants at Sierra typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Bret Taylor, former Salesforce co-CEO and Twitter board chair, and Clay Bavor, who led Google Labs, founded Sierra in 2023. The company builds 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.
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OptionsAhoy plans your Sierra equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.