Company equity guide
Stripe Employee Equity Tax Planning Guide
A tax-planning framework for Stripe employees with equity, including options, RSUs, tender or secondary liquidity, AMT, cost basis, and multi-state issues.
Direct answer
Stripe's public job materials describe equity compensation and recognize that employee programs can include stock options, RSUs, deferred compensation, and transaction-related issues. An employee's tax result depends on the actual grant and transaction. The practical work is to reconcile award type, exercise or settlement, tender eligibility, basis, state sourcing, and estimated tax before a liquidity window closes.
The decisions to put on one timeline
Separate current awards from owned shares
Unexercised options, unsettled RSUs, exercised shares, and shares acquired through prior transactions require different tax and liquidity analysis.
Review tender terms
Confirm eligible shares, sale limits, price, acceptance mechanics, settlement date, and whether payroll or brokerage reporting will apply.
Reconcile basis before sale
Exercise income or RSU compensation may not be fully reflected in broker-reported basis, so each lot should be checked before filing.
Compare this year with next year
A large transaction can interact with salary, bonus, other gains, AMT credit, charitable plans, and state residency across more than one year.
The tender price is only one input
An employee can sell a limited number of shares in a tender. Older ISO shares, NSO shares, and RSU shares have different basis and character, so default FIFO may not align with the employee's cash, AMT-credit, or gain objectives.
Simulated employee situation. LightUp Tax is not affiliated with Stripe, and this page does not describe or confirm any specific Stripe transaction.
What planning examines
Award and tender-document review
Lot-level basis and holding-period reconstruction
Sale and AMT-credit comparisons
Federal, state, and payment projections
What you receive
The work product should turn tax analysis into specific decisions, dates, and records that can be implemented.
Frequently asked questions
Is tender-offer income always a capital gain?
No. The result depends on the instrument and transaction. A stock sale can create capital gain or loss, while option exercise or cash-settled compensation may create wage income.
Can I choose which shares to tender?
Transaction documents and platform mechanics determine what is permitted. If lot selection is available, tax identification requirements and written broker confirmation should be addressed before settlement.
Why might Form 1099-B show the wrong basis?
For some employee stock acquired from options or compensation, broker-reported basis may exclude compensation already included in income. The return may require an adjustment supported by payroll and grant records.
Continue with a related guide
Tender Offer Tax Planning
Prepare for a private-company tender offer by reviewing eligible shares, award type, basis, holding period, tax lots, payroll reporting, state sourcing, and cash reserves.
Read the guideTax Lot and Specific Identification
Learn how tax-lot selection, FIFO, specific identification, basis, holding period, and AMT basis can change the tax result of a company-stock sale.
Read the guideRSU and Stock Cost Basis
Learn why employee-stock basis on Form 1099-B may need adjustment and how to reconcile RSU or option income with W-2, payroll, and broker records.
Read the guideNeed a complete tax projection?
Start with a short questionnaire. After reviewing your basic situation and main question, we will determine whether a 15-minute discovery call is the right next step.