Decision Cluster · Employee Stock Options

AI for Employee Stock Option Decisions

Most ESOPs are oversized and underused. Run yours through a CFO, an Investor, an Operator, an Empath, and a Skeptic — and design a pool that actually compounds team value without destroying the cap table.

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In short

Depends on stage and hiring plan. Pre-seed: 10-15%. Seed: 12-15%. Series A: 10-15%. Series B+: 5-10% replenishment. Investors push higher pools to pre-dilute; the CFO will pressure-test honestly.

Last reviewed October 1, 2026

An example

One ask, start to finish.
What comes back is a memo.

How a board takes a call like this: her read, who sits, what they ask first, then the call — with how sure they are, who disagreed and the first step.

Employee Stock Options

Example · Board of 3

How big should our ESOP pool be at Series A — 10%, 15%, 20%?

Chief of staff

This one needs a board: The CFO, The Investor and The Operator. The CFO pressure-tests unit economics, runway, and capital allocation. Each researches alone first, then they react to one another — and on a decision, two of them take opposed sides.

The CFOFinancial Controller
The InvestorVC Partner
The OperatorCOO

Asked first

Is the money for this already in the bank, or still promised?

In the bankPromisedNot yet

The board’s call

Set the pool at 12% post-Series A (not 15%).

12% pool is sufficient for most Series A companies; 15% over-dilutes founders. Refresh grants prevent the "fully vested and leaving" pattern at month 49.

Confidence73 · Moderate

The Operator disagreed

“Investor pressure usually pushes for larger pools — investor and CFO interests differ here”

First step Implement refresh grants at 0.10-0.25% annually for retained employees starting year 2.this week

Board of 3 · up to 135 credits on the card · an example, not a recorded run

Other asks people bring here

Several asks in one message become several rooms, each with its expert and its own price on the card. Keep or drop any, then convene them together.

Refresh grants — annual, milestone-based, or skip? — The Investor, up to 85 credits
Should we publish grant tables internally? — The Operator, up to 85 credits
ISO vs NSO for international employees? — The Empath, up to 85 credits

What you get

What she handles.
On this kind of call.

Pool size + budget

The board weighs pool size against your hiring plan, current team, and refresh strategy — usually oversized at seed by 30-50%.

Grant-level architecture

The Operator and Investor design level-based grant tables that scale with hire role and tenure.

Refresh + accelerator design

The Empath and CEO design refresh-grant policies and acceleration triggers that match retention needs.

Communication + literacy

The Marketer and Empath weigh how to communicate the ESOP so employees actually understand and value it.

Why SynthBoard

Why SynthBoard for this.
Not one voice. A board.

Whole-program framing

Most ESOP advice is about pool size; a board weighs pool, grants, refreshes, exercise windows, and communication as one system.

Refresh-focused

The Empath raises refresh grants — usually missing from the conversation.

Investor-vs-founder tension

The Skeptic flags when "standard pool" advice is actually investor-favorable, not company-optimal.

Policy doc on demand

Ask for a starter ESOP design and a consult writes the whole document — ready to iterate with your CFO and counsel.

Who sits

The experts for this call.
Each one holds a position.

Your Chief of Staff proposes who sits for the call, and every board is built with someone whose job is to argue against the obvious answer. Name an expert and they take a seat; tell her who you want on your board and they sit by default. How many seats a board has depends on your plan.

Financial Controller

The CFO

Revenue is a story. Cash is a fact. Show me the month the money runs out.

The CFO Financial Controller

Best on: Pricing, runway, discounts, and a hire you can barely afford.
Won’t let you: Confuse revenue with cash, or a signed deal with a paid one.

Try asking The CFO

Start with

The CFOOpen on every plan, Free included

Pick an expert

Hover, tap or tab throughSwipe, then tap one

GPT
Claude
Gemini
Grok

Seats are spread across model families: GPT, Claude, Gemini, Grok and more.

Questions

Fair questions.
Straight answers.

What people ask before they bring this call to a board.

How big should our ESOP pool be?

Depends on stage and hiring plan. Pre-seed: 10-15%. Seed: 12-15%. Series A: 10-15%. Series B+: 5-10% replenishment. Investors push higher pools to pre-dilute; the CFO will pressure-test honestly.

Should we offer refresh grants?

Almost always yes for retention — most senior employees become fully vested at month 49 and have nothing left to vest. The Empath will design a refresh cadence that fits your culture and pool budget.

Extended exercise windows — worth the cost?

Usually yes for tenured employees. 10-year windows are a recruitment and retention differentiator with manageable cap-table impact. The CFO and Investor will pressure-test the trade-off for your specific case.

How do we communicate option value to employees?

The Empath and Marketer will design education that's honest about both upside and downside. Most ESOP communication oversells, which produces disappointment, not motivation.

ISO vs NSO for international employees?

NSOs for non-US employees (ISOs are US-tax-specific); RSUs become attractive at later stage. The Lawyer will pressure-test for your geography mix.

Can the panel review our existing ESOP design?

Yes — paste the current structure (pool, grant levels, refresh policy, exercise windows) and the panel will pressure-test where it's leaving recruiting or retention value on the table.

SynthBoard (synthboard.ai) is one place for your business, your life, and every hard call. Your Chief of Staff keeps what you tell her on file, and 24 named experts on different AI models take the calls — one expert for a consult, a board with opposed seats for the hard ones — and hand back a memo with the call, the dissent and the first move. How it works.