compensation-strategy
Use this skill when benchmarking compensation, designing equity plans, building leveling frameworks, or structuring total rewards. Triggers on compensation benchmarking, equity grants, stock options, leveling, pay bands, total rewards, salary ranges, and any task requiring compensation strategy or structure design.
operations compensationequitylevelingpay-bandstotal-rewardsbenefitsWhat is compensation-strategy?
Use this skill when benchmarking compensation, designing equity plans, building leveling frameworks, or structuring total rewards. Triggers on compensation benchmarking, equity grants, stock options, leveling, pay bands, total rewards, salary ranges, and any task requiring compensation strategy or structure design.
compensation-strategy
compensation-strategy is a production-ready AI agent skill for claude-code, gemini-cli, openai-codex. Benchmarking compensation, designing equity plans, building leveling frameworks, or structuring total rewards.
Quick Facts
| Field | Value |
|---|---|
| Category | operations |
| Version | 0.1.0 |
| Platforms | claude-code, gemini-cli, openai-codex |
| License | MIT |
How to Install
- Make sure you have Node.js installed on your machine.
- Run the following command in your terminal:
npx skills add AbsolutelySkilled/AbsolutelySkilled --skill compensation-strategy- The compensation-strategy skill is now available in your AI coding agent (Claude Code, Gemini CLI, OpenAI Codex, etc.).
Overview
A structured framework for designing, benchmarking, and communicating compensation programs. This skill covers the full total rewards stack - from salary bands and equity grants to leveling frameworks and pay equity audits - with an emphasis on when to use each approach and how to justify decisions to candidates, employees, and leadership.
Tags
compensation equity leveling pay-bands total-rewards benefits
Platforms
- claude-code
- gemini-cli
- openai-codex
Related Skills
Pair compensation-strategy with these complementary skills:
Frequently Asked Questions
What is compensation-strategy?
Use this skill when benchmarking compensation, designing equity plans, building leveling frameworks, or structuring total rewards. Triggers on compensation benchmarking, equity grants, stock options, leveling, pay bands, total rewards, salary ranges, and any task requiring compensation strategy or structure design.
How do I install compensation-strategy?
Run npx skills add AbsolutelySkilled/AbsolutelySkilled --skill compensation-strategy in your terminal. The skill will be immediately available in your AI coding agent.
What AI agents support compensation-strategy?
This skill works with claude-code, gemini-cli, openai-codex. Install it once and use it across any supported AI coding agent.
Maintainers
Generated from AbsolutelySkilled
SKILL.md
Compensation Strategy
A structured framework for designing, benchmarking, and communicating compensation programs. This skill covers the full total rewards stack - from salary bands and equity grants to leveling frameworks and pay equity audits - with an emphasis on when to use each approach and how to justify decisions to candidates, employees, and leadership.
When to use this skill
Trigger this skill when the user:
- Benchmarks a role against market data (Levels.fyi, Radford, Mercer, Carta)
- Designs or revises pay bands for a level or job family
- Structures an equity grant (ISOs, NSOs, RSUs) or refresh program
- Builds or updates a leveling framework (IC and/or management tracks)
- Creates a total rewards package (salary + equity + benefits + perks)
- Conducts or responds to a pay equity audit
- Writes or revises a compensation philosophy document
- Explains compensation structure to a candidate or employee
Do NOT trigger this skill for:
- Recruiting sourcing tactics or interview process design (use a hiring skill)
- Payroll processing, tax withholding, or benefits administration (use an HR operations skill)
Key principles
Pay transparency builds trust - Employees who understand how pay is determined are more engaged and less likely to leave over perceived unfairness. Document your philosophy, publish band ranges internally, and explain progression criteria clearly. Opacity breeds resentment.
Market data, not gut feel - Compensation decisions made from intuition drift out of market over time and introduce bias. Anchor every band to at least two external data sources refreshed annually. "We've always paid this way" is not a compensation strategy.
Total rewards, not just salary - Base salary is one line in a larger equation. Equity upside, health benefits, PTO policies, remote flexibility, and career development all have real economic value. Design and communicate the full package - candidates and employees do math.
Equity is a retention tool - Equity without a vesting schedule is a signing bonus. Structure grants to align long-term incentives: 4-year vesting with a 1-year cliff is the standard, but refresh grants and accelerated vesting on change-of-control matter equally. Design equity with departure scenarios in mind.
Review annually at minimum - Markets move. Inflation erodes purchasing power. Competitors raise bands. A compensation structure that was competitive 18 months ago may be 15% below market today. Schedule mandatory annual reviews; trigger ad-hoc reviews when attrition spikes or a survey shows significant movement.
Core concepts
Compensation components
| Component | Description | Typical form |
|---|---|---|
| Base salary | Fixed annual cash paid on regular schedule | Bi-weekly or semi-monthly paycheck |
| Variable/bonus | Performance-linked cash paid periodically | Annual bonus, quarterly MBO, commission |
| Equity | Ownership stake in the company | ISOs, NSOs, RSUs, ESPP |
| Benefits | Non-cash protections and programs | Health, dental, vision, 401(k) match |
| Perks | Discretionary extras | Remote stipend, L&D budget, PTO |
Total compensation (TC) = base + expected bonus + annualized equity value + benefits value. When comparing offers or setting bands, always use TC - base-only comparisons are misleading, especially at senior levels where equity is the majority of value.
Market percentiles
Compensation surveys report pay at percentiles of the market. The standard anchor points:
| Percentile | What it means | Typical use |
|---|---|---|
| P25 | 25% of market pays less | Below-market, acceptable for high-equity early-stage |
| P50 (median) | Middle of market | Default anchor for most companies |
| P75 | 25% of market pays more | Above-market, used to compete for talent in hot roles |
| P90 | Top decile | Reserved for critical roles or FAANG-adjacent competition |
Most companies target P50 base + P75 equity, or P75 base + P50 equity. Decide your strategy based on what stage you are at and where you want to compete.
Pay bands
A pay band (or salary range) defines the minimum, midpoint, and maximum for a given level. Key parameters:
- Spread: max - min, expressed as a percentage of the midpoint. Typically 50-80% for individual contributor roles. Wider bands allow more flexibility; narrower bands reduce manager discretion.
- Midpoint: the target market rate (usually P50 or P75 of survey data).
- Overlap: adjacent bands share some salary range, allowing a high performer at L3 to earn more than a new hire at L4 without an immediate promotion.
- Compa-ratio: employee's salary / midpoint. 100% = exactly at midpoint. Ranges of 85-115% are typical. Outside this range triggers a review.
Equity types
ISOs (Incentive Stock Options), NSOs (Non-Qualified Stock Options), and RSUs
(Restricted Stock Units) are the three main forms. See
references/equity-guide.md for detailed comparison, tax treatment, and vesting
patterns.
Vesting schedules
The standard is 4-year total vesting with a 1-year cliff:
Year 1: 0% vests (cliff period) -> 25% vests at 12-month cliff
Years 2-4: monthly vesting at 1/48th of total grant per monthVariations to know:
- Back-weighted vesting (10/20/30/40): rewards long tenure, retains people longer but feels unfair early on
- Monthly from day one (no cliff): common at later-stage or public companies for senior hires
- Refresh grants: new grants issued annually or at promotion to top up unvested equity and reset retention incentives
- Acceleration: single-trigger (on change of control) or double-trigger (on change of control + involuntary termination) - always use double-trigger for employees
Common tasks
Benchmark a role against market
Goal: Determine whether current or proposed pay is competitive.
Data sources by use case:
| Source | Best for | Cost |
|---|---|---|
| Levels.fyi | Public tech companies, IC engineering/PM | Free |
| Carta Total Comp | Startups (pre-IPO), equity benchmarking | Paid |
| Radford (Aon) | Enterprise tech, broad job families | Paid (survey participation) |
| Mercer | Non-tech industries, HR and operations roles | Paid |
| Glassdoor / LinkedIn Salary | Directional check, wide variance | Free |
| Option Impact / J.Thelander | VC-backed startup equity norms | Paid |
Methodology:
- Define the job family and level precisely (use internal level definitions)
- Pull data from at least two sources at the same percentile target
- Normalize to the same geographic region (use location factors for remote roles)
- Compare TC, not just base (include equity at current 409A or public price)
- Document sources, date pulled, and percentile used - this becomes the audit trail
If two sources diverge by more than 15%, pull a third source and average the two closest. Do not cherry-pick the lowest to justify underpaying.
Design pay bands
Step-by-step:
- Decide your percentile target (P50 for market-rate, P75 for above-market)
- Set the midpoint to that percentile for each level
- Apply a spread: 50% spread means min = midpoint * 0.75, max = midpoint * 1.25
- Check band overlap: adjacent bands should overlap 15-25% to allow flexibility
- Validate existing employees fall within or near their band (flag outliers)
- Set a review cadence (annually minimum; trigger on survey data shifts >5%)
Example band structure for a 4-level IC track:
| Level | Midpoint | Min (75%) | Max (125%) |
|---|---|---|---|
| L1 | $100k | $75k | $125k |
| L2 | $130k | $98k | $163k |
| L3 | $170k | $128k | $213k |
| L4 | $220k | $165k | $275k |
Bands should be wide enough to reward growth within a level without requiring promotion, but narrow enough that managers cannot rationalize dramatically underpaying new hires.
Structure equity grants
Equity grant amounts depend on company stage, role level, and market norms. Starting guidelines (adjust for company-specific dilution expectations):
| Stage | Level | Typical initial grant | Form |
|---|---|---|---|
| Seed (pre-product) | Senior IC | 0.25-0.75% | Common / ISO |
| Series A | Senior IC | 0.10-0.30% | ISO |
| Series B/C | Staff / L5 | 0.05-0.15% | ISO |
| Series D+ / late stage | Staff / L5 | 0.02-0.06% | ISO or RSU |
| Public company | Staff / L5 | $150k-$400k value | RSU |
Grant sizing process:
- Determine grant value in dollars (use 409A for private; use 30/60/90-day average for public)
- Divide by share/unit price to get share count
- Set a 4-year vesting schedule with 1-year cliff (standard)
- Document the refresh cadence (typically annual, sized at 25% of initial grant)
Build a leveling framework
A leveling framework defines career progression expectations. The minimum a useful framework must specify per level:
- Scope: what is the person responsible for? (task, project, domain, org)
- Impact: what outcomes are expected? (individual, team, company)
- Execution: how do they work? (guidance needed, independent, leads others)
- Communication: who do they influence? (peers, team, leadership, external)
IC track skeleton (5 levels):
| Level | Title | Scope | Impact |
|---|---|---|---|
| L1 | Associate | Assigned tasks | Completes reliably with mentorship |
| L2 | Mid-level | Small projects | Delivers independently |
| L3 | Senior | Full projects, owns domain | Elevates team quality |
| L4 | Staff | Cross-team initiatives | Org-level influence |
| L5 | Principal | Company-wide problems | Sets technical direction |
Add a parallel management track starting at the Senior equivalent where team leads split from IC. Keep the IC track viable all the way - not everyone wants to manage and forcing the path creates attrition.
Design a total rewards package
Total rewards = compensation + benefits + perks + culture/career. When structuring a package for a role or level:
- Anchor base salary to market data at your chosen percentile
- Set equity using stage-appropriate grant sizing guidelines above
- Layer benefits: health (medical/dental/vision), 401(k) with match, life/disability insurance - these are table-stakes for any full-time role
- Add perks that align with your culture: remote stipends, L&D budgets, wellness allowances, parental leave beyond statutory minimums
- Document the full TC in offer letters and annual statements so employees understand the total value - most people underestimate the cost of benefits
Remote-first companies: publish a location factor policy upfront. Paying San Francisco rates to everyone is expensive; paying rural rates to people in NYC creates resentment. Tiered geographic zones are the standard approach.
Handle pay equity audits
Pay equity audits detect and correct unjustified pay differences between employees doing similar work, typically analyzed by gender, race, and ethnicity.
Audit process:
- Define comparable groups (same level, same job family, similar tenure band)
- Run regression analysis controlling for legitimate pay factors (level, tenure, performance rating, location)
- Calculate adjusted pay gaps: differences remaining after controlling for legitimate factors
- Set a remediation threshold (commonly: flag gaps >5% in adjusted analysis)
- Correct identified gaps in the next compensation cycle, not "eventually"
- Repeat annually; document findings and remediation actions
Conducting an audit does not create legal liability - failing to conduct one and being unable to explain pay gaps does. The audit creates the paper trail that demonstrates good-faith effort.
Communicate compensation philosophy
A compensation philosophy statement answers five questions:
- What market percentile do we target and why?
- How do we think about total rewards vs. cash-only?
- How is equity structured and what does it mean for employees?
- How does pay progress with performance and tenure?
- How often do we review and adjust pay?
Write it in plain language. Avoid jargon. Publish it to all employees, not just HR. Update it when strategy changes. A philosophy that cannot be explained in a 10-minute conversation is not a philosophy - it is a policy document that no one will read.
Anti-patterns
| Anti-pattern | Why it's wrong | What to do instead |
|---|---|---|
| Setting pay from the last person's salary | Anchors new hire pay to arbitrary history, not market; propagates historical bias | Pull fresh market data for every open role before setting the offer range |
| Exploding or "take it or leave it" offers | Creates resentment, signals bad faith, and causes candidates to question company culture | Give candidates reasonable time (3-5 business days minimum) and explain all components |
| No equity refresh grants | Unvested equity drops to zero at tenure milestones; employees become "golden handcuff free" and leave | Issue annual refreshes sized at 25-50% of initial grant; tie to performance rating |
| Compression - new hires paid more than tenured employees | Destroys morale when discovered; tenure becomes a penalty | Audit for compression when setting new hire offers; adjust tenured pay in same cycle |
| Subjective performance ratings driving pay | Introduces manager bias into compensation; obscures actual criteria | Use calibrated, criteria-based performance rubrics tied to level expectations |
| Designing equity without tax guidance | Employees make poor exercise decisions due to AMT, 83(b) elections, and QSBS; creates legal exposure | Provide a tax FAQ, recommend personal tax advisors, and document ISO/NSO differences |
Gotchas
ISO exercise triggers AMT - Exercising Incentive Stock Options creates a tax preference item that can trigger Alternative Minimum Tax, even if the employee doesn't sell the shares. Employees who exercise a large ISO grant in a high-valuation year can owe six-figure AMT bills on paper gains that aren't yet liquid. Always flag the AMT risk and recommend personal tax advice before any ISO exercise.
Pay compression discovered at offer stage - A new hire offer above the band midpoint that crosses or approaches a tenured employee's salary creates compression. If the tenured employee finds out (and they often do), it destroys morale and accelerates attrition. Audit the band for compression before finalizing any offer, not after.
Equity value communicated as strike price, not FMV - Candidates often misunderstand option grants because the hiring team presents the strike price ("you get options at $0.50/share") without explaining current 409A fair market value and the implied spread. Communicate equity value as both the grant size and the estimated current value so candidates can do real math.
Geographic pay policy announced after hiring - Introducing a location-tiered pay policy after hiring remote employees at a flat rate triggers immediate resentment. Those hired at SF rates and later adjusted to their local tier feel a retroactive pay cut. Establish and communicate the geographic policy before the first offer, not when the policy becomes a cost problem.
Refresh grant eligibility not documented - If the company has no written policy on who gets refresh grants and when, managers informally grant them to favorites and skip others with equal performance. This becomes a pay equity finding and a legal exposure. Document the refresh cadence, eligibility criteria, and sizing formula before the first refresh cycle.
References
For detailed guidance on specific compensation topics, read the relevant file
from the references/ folder:
references/equity-guide.md- ISO vs NSO vs RSU comparison, vesting patterns, tax treatment, early exercise, 83(b) elections, QSBS
Only load a references file when the current task specifically requires it - they are detailed and will consume context.
References
equity-guide.md
Equity Guide: ISO vs NSO vs RSU
Practical reference for understanding equity compensation instruments, their tax implications, and vesting patterns. This guide is informational - always recommend employees consult a personal tax advisor before making exercise or election decisions.
1. Instrument Comparison
| Attribute | ISO | NSO | RSU |
|---|---|---|---|
| Full name | Incentive Stock Option | Non-Qualified Stock Option | Restricted Stock Unit |
| Who can receive | Employees only | Employees, contractors, advisors, board | Employees (primarily) |
| Tax on grant | None | None | None |
| Tax on vest | None | None | Ordinary income on FMV at vest |
| Tax on exercise | Possible AMT preference item | Ordinary income on spread (FMV - strike) | N/A (RSUs vest, not exercised) |
| Tax on sale | Capital gains (long-term if holding rules met) | Capital gains on any appreciation after exercise | Capital gains on appreciation after vest |
| Withholding required | No | Yes - employer withholds at exercise | Yes - employer withholds at vest |
| ISO holding rule | 2 years from grant + 1 year from exercise | None | None |
| Maximum grant | $100k per year (at exercise, by FMV at grant) | No statutory limit | No statutory limit |
| Value when issued | Only valuable if stock appreciates above strike | Only valuable if stock appreciates above strike | Always has value equal to current FMV |
| Strike price required | Yes - must equal FMV at grant (409A) | Yes - typically FMV at grant | No - no strike price |
| Best for | Early-stage employees; low FMV = low tax risk | Advisors, contractors, late grants above $100k ISO cap | Late-stage or public companies; predictable value |
2. ISO - Incentive Stock Options
How they work
ISOs grant the right to purchase shares at a fixed price (the strike price, set at FMV on the grant date via 409A valuation) for a defined period (typically 10 years from grant, or 90 days after termination).
An employee does not pay tax when ISOs are granted. Tax events occur at:
- Exercise: no regular income tax, but the spread (FMV - strike) is an AMT preference item - it counts toward Alternative Minimum Tax calculations
- Sale: if ISO holding rules are met, the entire gain from strike to sale price is taxed at long-term capital gains rates (currently 20% max federal)
ISO holding rules
To get the favored long-term capital gains treatment, shares acquired via ISO exercise must be held for the longer of:
- 2 years from the grant date
- 1 year from the exercise date
Selling before both holding periods are satisfied creates a disqualifying disposition - the spread at exercise is reclassified as ordinary income.
AMT risk
The spread at ISO exercise is an AMT preference item. In years where employees exercise large ISO grants, their AMT bill can be substantial even if they do not sell the shares. This is the primary reason employees should consult a tax advisor before exercising ISOs, especially at high-FMV companies.
Mitigation strategies:
- Exercise early (83(b) election) when FMV is near the strike price
- Exercise in tranches across tax years to spread AMT exposure
- Keep track of AMT credits generated - they can be used to offset future regular tax once the ISO shares are sold
ISO $100k limit
ISOs that become exercisable in a single year are limited to $100,000 in FMV (measured at the grant date). Amounts above this automatically convert to NSOs. For high-value senior grants, this limit means part of the grant is always NSOs.
3. NSO - Non-Qualified Stock Options
How they work
NSOs work mechanically the same as ISOs - a fixed strike price, an exercise window, and the right to purchase shares - but the tax treatment is less favorable.
Tax events:
- Exercise: the spread (FMV at exercise - strike price) is ordinary income, reported on the W-2 (employees) or 1099 (contractors). The employer must withhold taxes at exercise.
- Sale: any appreciation from FMV at exercise to sale price is capital gains (long-term if held > 1 year after exercise)
Who gets NSOs
- Contractors, advisors, and board members (cannot receive ISOs)
- Employees receiving grants above the $100k ISO limit
- Employees at companies that choose to use NSOs for simplicity
NSO tax planning
Since exercise triggers ordinary income, employees with NSOs need to plan around:
- Cash needed to cover both the purchase price and the tax withholding at exercise
- Whether to exercise pre-liquidity (betting on appreciation) or wait until a liquidity event (simpler but concentrates risk)
- Post-termination exercise window: standard is 90 days, but some companies extend to 5 or 10 years for NSOs specifically to reduce departure tax pressure
4. RSU - Restricted Stock Units
How they work
RSUs are a promise to deliver shares (or the cash equivalent) on a future date, contingent on meeting a vesting condition (time-based, performance-based, or both). There is no strike price - the RSU holder receives the full FMV of the shares at vesting.
Tax events:
- Vest: the FMV of the shares on the vesting date is ordinary income, reported on the W-2. The employer withholds taxes, typically by withholding a portion of the vesting shares (sell-to-cover)
- Sale: any appreciation from FMV at vest to sale price is capital gains
Why RSUs are common at later stages
At early-stage companies, the 409A strike price is low, making options attractive (small spread = small tax event at exercise). At later stages, the 409A rises close to preferred share prices - exercising options with a high FMV spread creates immediate large tax bills. RSUs avoid this: tax is deferred to vest, and the shares have known value when the tax event occurs.
For public companies, RSUs are the standard instrument because:
- Employees can immediately sell vesting shares to cover taxes
- No cash required to exercise
- No AMT risk
- Predictable value at grant based on current stock price
RSU double-trigger vesting (private companies)
Private company RSUs often use double-trigger vesting: shares vest only when both (1) the time-based schedule is satisfied AND (2) a liquidity event occurs (IPO or acquisition). This avoids the tax problem of vesting shares that cannot be sold (would trigger income tax with no cash to pay it).
Without double-trigger, a private company RSU creates a taxable income event at vesting with no way to sell shares to cover the tax.
5. Vesting Patterns
Standard 4-year monthly with 1-year cliff
The most common structure for startup employees:
Grant date: January 1, Year 0
Grant: 48,000 shares
Year 1 (cliff):
- Months 1-11: 0 shares vest
- Month 12 (January 1, Year 1): 12,000 shares vest (25% cliff)
Years 2-4:
- Months 13-48: 1,000 shares vest per month
- 36 months * 1,000 = 36,000 shares
Total at 48 months: 48,000 shares (100%)Purpose of the cliff: Protects the company from very early departures - someone who leaves at month 6 receives no equity. Creates a meaningful milestone at the 1-year mark.
Back-weighted vesting (10/20/30/40)
Some companies use a schedule that grants more equity in later years:
Year 1: 10% vests
Year 2: 20% vests
Year 3: 30% vests
Year 4: 40% vestsThis maximizes retention incentive in years 3 and 4 but feels slow to early employees. Less common than standard cliff vesting.
Immediate/monthly from day one (no cliff)
Used for senior hires or at mature companies where the cliff is seen as hostile. Shares vest monthly from the start date, often at 1/48th per month. Increases departure risk in the first year.
Performance-based vesting
Vesting tied to achieving specific milestones (revenue targets, product launches, funding rounds). Common for:
- Founder grants at investor-backed companies
- Executive compensation packages
- Sales roles (blended with time-vesting)
Mixed structures (50% time / 50% performance) are common for executives.
Refresh grants
Refresh grants are new option or RSU grants issued to existing employees to maintain ongoing retention incentives as initial grants vest out. Standard practice:
- Frequency: annually, or at promotion
- Sizing: typically 25-50% of the initial grant value
- Timing: often issued at the same time as annual performance reviews
- Cliff: refresh grants sometimes carry a shorter 6-month cliff or no cliff since the employee has already proven tenure
Without a refresh program, every tenured employee eventually becomes fully vested and has no equity-based reason to stay. Model the vesting curve for your team annually to identify "vesting cliffs" before attrition spikes.
6. Early Exercise and 83(b) Elections
Early exercise
Some option grants (typically ISOs at early-stage startups) include the right to early exercise: purchasing shares before they vest. The shares are subject to a repurchase right by the company that lapses as the normal vesting schedule would have occurred.
Why early exercise matters: Exercising options at a very low 409A (common in seed/pre-seed companies) minimizes the taxable spread at exercise and starts the capital gains holding clock early.
83(b) election
When shares are received subject to vesting conditions (restricted shares or early-exercised options), an 83(b) election allows the holder to elect to pay taxes based on the current FMV rather than waiting for vesting.
Requirements:
- Must be filed with the IRS within 30 days of receiving the restricted shares - this deadline is absolute and cannot be extended
- A copy must be attached to the employee's tax return for the year of election
When it makes sense:
- Early-stage company with very low 409A - the spread and FMV are both near zero, so the tax event is negligible
- Strong conviction the company will grow significantly (locking in capital gains treatment on the full appreciation)
When it does not make sense:
- Large spread at exercise (large immediate tax bill with no liquidity)
- Uncertain company prospects (paying taxes on value you may never realize)
- Company fails - the tax paid is lost and only partially recoverable as a capital loss
7. QSBS - Qualified Small Business Stock
Section 1202 of the IRS code provides a federal capital gains exclusion of up to $10 million (or 10x the investor's basis, whichever is greater) on the gain from selling QSBS, if:
- Stock was issued by a domestic C-corporation
- The corporation had gross assets under $50 million when the stock was issued
- The holder has held the stock for more than 5 years
- The stock was acquired at original issuance (not secondary market)
- The corporation is in a qualifying trade or business (most tech startups qualify; professional services, finance, and hospitality generally do not)
Employees who early-exercise ISOs or purchase restricted shares at a very early stage may be eligible for QSBS treatment, potentially eliminating federal taxes on up to $10M of gain. State taxes vary - California, for example, does not conform to the federal QSBS exclusion.
QSBS analysis requires a tax attorney or CPA. The rules are complex and fact-specific. This section is informational only.
Quick Decision Reference
"Which instrument should we grant to this person?"
- Employee, early-stage, low 409A -> ISO (+ recommend 83(b) if early exercise available)
- Employee, grant exceeds $100k ISO limit -> Split: ISO up to $100k, NSO for remainder
- Advisor or contractor -> NSO only (ISOs are not available)
- Employee, late-stage or public company -> RSU
- Senior executive requiring large grant -> RSU or NSO depending on stage
"Should I early exercise?"
- 409A is very low (near par value) + strong conviction in company -> Yes, and file 83(b) within 30 days
- 409A has risen significantly + large spread -> Consult tax advisor first; AMT risk may be high
"When should I tell employees about QSBS?"
- At grant, if the company qualifies - employees who early exercise may start the 5-year clock immediately
- Again at Series B/C when valuation growth makes the potential exclusion material
Frequently Asked Questions
What is compensation-strategy?
Use this skill when benchmarking compensation, designing equity plans, building leveling frameworks, or structuring total rewards. Triggers on compensation benchmarking, equity grants, stock options, leveling, pay bands, total rewards, salary ranges, and any task requiring compensation strategy or structure design.
How do I install compensation-strategy?
Run npx skills add AbsolutelySkilled/AbsolutelySkilled --skill compensation-strategy in your terminal. The skill will be immediately available in your AI coding agent.
What AI agents support compensation-strategy?
compensation-strategy works with claude-code, gemini-cli, openai-codex. Install it once and use it across any supported AI coding agent.