Finance playbook · AI Employee: Fin

Equity & Stock Option Support

Employee equity questions answered same day

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The problem

Equity questions are the most-important-least-answered category in HR / finance. Employees receive option grants they don't fully understand, don't know their vesting schedule, don't know how to exercise, panic about tax implications, and pester HR + finance with the same questions. Answers require judgment (tax implications vary), grants (each grant has different terms), and speed (option-exercise deadlines are unforgiving). Manual answers are slow, inconsistent, and occasionally wrong in expensive ways.

At a glance
Trigger
Chat + form
Approvals
None (all writes via Carta)
What it does
Read-only
Systems
Carta · Payroll
How it feels in production

An hour-by-hour walkthrough.

Priya asks Fin: "I have 8,000 options vesting next month. Should I exercise them?" Fin looks up Priya's grant record in Carta: - Grant 1: 12,000 ISOs granted 2023-04-15, 4-year vest with 1-year cliff, strike $2.40 - Vested to date: 6,000 (50%) - Next vest: 250 shares on the 15th of each month, 8,000 next month means it's likely the 3-year milestone (25% additional cliff) - Current 409A: $18.60 (last board-approved valuation, dated 2026-08) - Exercise cost for 8,000: $19,200 ($2.40 × 8,000) - Tax exposure at exercise (ISO): AMT on ($18.60 − $2.40) × 8,000 = $129,600 spread, may create $30-45K AMT bill depending on personal tax situation Fin responds: "You have 8,000 options vesting next month at strike $2.40. Exercise cost: $19,200. Current 409A is $18.60, so the paper gain is $129,600 which triggers AMT considerations (typical AMT exposure $30-45K, depends on your tax situation). This is a tax-significant decision. I can: 1. Send you the details in an exportable format for your tax advisor. 2. Point you to our equity-decision guide (framework for exercise timing). 3. Schedule a session with our equity advisor Carta Financial Advisors (covered by company benefit). Please note I don't provide personalised tax advice — this is informational only." Priya requests all three. Fin schedules the advisor session for next week, sends the exportable summary, and links the decision guide. Every question tracked; unanswered patterns feed the FAQ + advisor prep.
How it works

Step by step.

  1. 01

    Recognize equity question + look up grants

    Question intent classification. Employee equity records from Carta / Shareworks / Pulley. Handles multi-grant employees (ISOs, NSOs, RSUs, ESPP).

    Reasoning · Carta · Shareworks · Pulley
  2. 02

    Compute mechanics (vesting, exercise cost, spreads)

    Vesting schedule + next vest date. Exercise cost. Current 409A × shares = paper spread. AMT / income-tax classification (ISO vs. NSO vs. RSU).

    Grant terms · 409A valuation · Tax classification
  3. 03

    Present with clear disclaimer + advisor path

    Numbers presented factually. Explicit disclaimer: informational not tax advice. Path to actual advisor (external, covered by benefit or self-arranged).

    Slack · Teams · Advisor scheduling · Decision guide
  4. 04

    Execute exercises with proper flow

    Exercise requests routed through Carta with employee signature + payment. Company countersign + tax withholding + stock issuance. Confirmations to employee.

    Carta · Payment processing · Stock transfer agent
  5. 05

    Escalate tax-significant + regulated questions

    Complex tax scenarios, 83(b) elections, section 409A concerns, private-secondary transactions escalate to legal + qualified advisors. Fin never substitutes for legal + tax advice.

    Legal · Tax advisor referral · Compliance escalation
Systems and wiring

What you connect to make this run.

Carta · Shareworks · Pulley · Equity platform

read+write

Grant data + vesting + exercise operations. Fin reads for questions; writes exercises + reports through the platform.

409A valuation reports

read

Current + historical 409A for exercise-timing calculations. Refresh cadence tracked; stale valuations noted.

Tax advisor referral network

read+write

External advisors covered by company benefit (Origin, Wealthramp, or similar). Fin schedules sessions but never replaces the advisor.

Legal · Compliance

read

Complex equity structures (early-exercise, secondary sales, dual-class shares) escalate here. Fin defers rather than guessing.

What changes

Before and after, honestly.

Time to answer equity questions
Before
1-14 days
After
Under 5 minutes for informational
Employees using equity benefit correctly
Before
40-65%
After
80-92% (informed decisions)
HR/finance hours per week on equity questions
Before
8-15 hours
After
1-2 hours
Missed exercise deadlines (post-departure)
Before
5-15 per year
After
Under 1
Related

Playbooks that pair with this one.

HR

Employee Offboarding

Post-termination exercise windows are a common source of questions.

HR

Compensation Requests

Equity refreshes flow through the comp-request approval mechanism.

Finance

T&E Policy Q&A

Same Q&A pattern for policy-adjacent questions.

Frequently asked

Answers about this playbook.

What if the employee wants specific tax advice?

Fin never gives tax advice. Refers to company-provided advisor benefit or the employee's own advisor. Numbers factual; interpretation by qualified professional.

How does it handle early-exercise structures?

Early-exercise with 83(b) is common at startups; Fin surfaces the option with the deadline warning (83(b) is 30 days from grant, irreversible). Routes to legal for the actual filing.

Can it handle secondary tender offers?

Yes — during tender offer windows, Fin surfaces the offer terms, participation deadlines, and tax implications. Never advises on participation; provides the mechanics.

How does it handle multi-jurisdiction employees (equity across countries)?

Country-specific tax treatments considered. Some jurisdictions have qualified plans (UK EMI, France BSPCE) with different tax profiles. Fin flags jurisdictional considerations; advisor for actuality.

What about ex-employees exercising post-departure?

Post-termination exercise window is 90 days for ISOs (typically), longer for extended windows. Fin reminds ex-employees of upcoming deadlines to prevent expiration.

See it run on your data.

Free plan, no credit card. Connect the systems this playbook needs and run it against a past event first.

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