This recipe produces three deliverables for startups hiring their first workers: (1) a Worker Classification Decision Matrix that determines whether each role should be structured as employee or contractor based on jurisdiction-specific legal tests, (2) an Employment Compliance Checklist covering mandatory registrations, insurance, withholding, and notices, and (3) an Equity Compensation Setup Plan specifying the optimal equity vehicle, valuation requirements, and tax implications per jurisdiction. [src1]
Which path?
├── Hiring in US only, <10 employees
│ └── PATH A: US DIY -- Gusto/Justworks + Carta + local attorney
├── Hiring in US only, 10+ employees
│ └── PATH B: US Scaled -- Rippling + Carta + employment law firm
├── Hiring internationally, <10 people
│ └── PATH C: Global Lean -- Deel/Remote (EOR) + Carta/Equidam
└── Hiring internationally, 10+ people
└── PATH D: Global Scaled -- Deel/Rippling + Carta + multi-jurisdiction law firm
| Path | Tools | Cost/mo | Setup Time | Compliance Coverage |
|---|---|---|---|---|
| A: US DIY | Gusto + Carta + attorney | $100-300 | 1-2 weeks | US single-state |
| B: US Scaled | Rippling + Carta + law firm | $500-2,000 | 2-4 weeks | US multi-state |
| C: Global Lean | Deel/Remote EOR + Equidam | $600-1,500 | 1-3 weeks | 150+ countries via EOR |
| D: Global Scaled | Deel/Rippling + Carta + law firm | $2,000-10,000 | 4-8 weeks | Full global coverage |
Duration: 2-4 hours per jurisdiction · Tool: Classification decision framework
For each role in the hiring plan, apply the jurisdiction-specific classification test to determine whether the worker must be an employee or can legally be a contractor.
US CLASSIFICATION DECISION TREE:
1. Does the company control HOW the work is done (not just WHAT)?
YES → Likely employee
NO → Continue
2. Does the company provide tools, workspace, or set hours?
YES → Likely employee
NO → Continue
3. Is the work a core part of the company's business?
(California ABC Test, Prong B)
YES → Employee in ABC-test states (CA, NJ, MA, IL + 30 others)
NO → Continue
4. Does the worker have their own business, serve other clients,
and control their own profit/loss?
YES → Likely contractor
NO → Likely employee
UK IR35 CLASSIFICATION:
1. Control: Does the client dictate how/when/where work is done?
2. Substitution: Can the worker send a replacement?
3. Mutuality of obligation: Is there ongoing obligation to offer/accept work?
All 3 point to employment → Inside IR35 (employee for tax purposes)
Verify: For each role, document the classification rationale citing the specific legal test applied · If failed: If classification is ambiguous, default to employee status (safer) or engage employment counsel
Duration: 1-3 days · Tool: Government portals + payroll provider
Register with all required government agencies before the first worker starts.
US EMPLOYER REGISTRATION CHECKLIST:
Federal:
[ ] EIN obtained (IRS Form SS-4 or online)
[ ] E-Verify enrollment (mandatory in some states)
Per state where workers are located:
[ ] State tax withholding account registered
[ ] State unemployment insurance (SUI) account
[ ] Workers compensation insurance purchased
[ ] New hire reporting registered
[ ] State-specific posters obtained
UK EMPLOYER REGISTRATION CHECKLIST:
[ ] PAYE scheme registered with HMRC (before first payday)
[ ] Workplace pension provider selected (auto-enrolment required)
[ ] Employers liability insurance obtained (legally mandatory)
[ ] Employment contract issued (written statement required from day 1)
[ ] Right-to-work check completed
Verify: All registrations confirmed with account numbers. Payroll provider connected to each tax account · If failed: If state registration is delayed, do not allow worker to start. Use EOR as interim solution if urgent
Duration: 2-4 hours per jurisdiction template · Tool: Legal templates + attorney review
Draft jurisdiction-compliant employment agreements with required elements for each location.
US EMPLOYMENT AGREEMENT -- REQUIRED ELEMENTS:
- At-will employment statement (except Montana)
- Job title, duties, reporting structure
- Compensation: salary/hourly rate, pay frequency, overtime eligibility
- Benefits summary (health insurance if 50+ FTE under ACA)
- Confidentiality and IP assignment clause
- Non-compete (if legal -- banned in CA, MN, OK, ND)
UK EMPLOYMENT CONTRACT -- REQUIRED FROM DAY 1:
- Names, start date, job title, place of work
- Pay rate and intervals, hours of work
- Holiday entitlement (min 28 days incl. bank holidays)
- Pension details (auto-enrolment min 8% total)
- Notice periods, probation, grievance procedures
Verify: Attorney has reviewed template for each jurisdiction. IP assignment clause covers all work product · If failed: Use vetted templates from Clerky (US), SeedLegals (UK), or your EOR provider
Duration: 4-8 hours · Tool: Carta, Equidam, or SeedLegals + tax advisor
Select and implement the right equity vehicle for each jurisdiction. [src5] [src6]
EQUITY VEHICLE BY JURISDICTION:
US (Delaware C-Corp):
Preferred: ISOs -- no tax at grant/exercise if held 1yr+ after exercise
Requires: 409A valuation ($2,500-$9,000), board-approved plan
Limit: $100K/year exercisable value per employee
UK:
Preferred: EMI Options -- CGT rate (10-20%) vs income tax (up to 45%)
From Apr 2026: eligible if <500 employees AND <GBP 120M gross assets
Per-employee limit: GBP 250K; company limit: GBP 6M (from Apr 2026)
Germany:
Preferred: VSOP -- tax only on cash payout at exit event
Avoids "dry income" problem of real ESOPs
France:
Preferred: BSPCE -- flat 12.8% on gains if held 1yr+
Verify: 409A or HMRC valuation completed before any option grants. Board resolution signed · If failed: Do not issue options without valuation. Promise letters acceptable as interim
Duration: 2-4 hours · Tool: Payroll provider + benefits broker
Configure mandatory minimums for each jurisdiction where employees work.
US MINIMUM REQUIREMENTS (2026):
Federal minimum wage: $7.25/hr
California: $16.90/hr | New York (NYC): $16.50/hr
Exempt salary threshold: $58,656/yr (federal), $70,304/yr (CA)
Overtime: 1.5x for >40 hrs/week (FLSA)
UK MINIMUM REQUIREMENTS (Apr 2025):
National Living Wage (21+): GBP 12.21/hr
Holiday: 28 days/year | Pension: 8% total (3% employer min)
Maternity: 52 weeks leave, 39 weeks statutory pay
Verify: Payroll system correctly calculates minimum wage, overtime, and withholding for each worker's location · If failed: If payroll provider does not support a specific jurisdiction, switch to EOR
Duration: 1-2 hours setup · Tool: Calendar + payroll provider alerts
Set up recurring compliance deadlines to avoid penalties.
MONTHLY: Payroll tax deposits, PAYE remittance (UK: by 22nd)
QUARTERLY: Form 941 (US), state payroll tax filings
ANNUALLY: W-2s/1099s (Jan 31), 409A renewal, EMI return (Jul 6)
TRIGGERED: New state registration, funding round (new 409A), termination
Verify: All calendar items have responsible owner and automated reminders · If failed: If a filing deadline is missed, file immediately. IRS late 941 penalties: 2-15% of unpaid tax
{
"output_type": "employment_law_compliance_package",
"format": "JSON",
"columns": [
{"name": "role_title", "type": "string", "description": "Job title or role name"},
{"name": "jurisdiction", "type": "string", "description": "Country and state/region"},
{"name": "classification", "type": "string", "description": "employee or contractor"},
{"name": "classification_test", "type": "string", "description": "Legal test applied"},
{"name": "classification_risk", "type": "string", "description": "low/medium/high"},
{"name": "minimum_wage_applicable", "type": "number", "description": "Applicable rate"},
{"name": "mandatory_benefits", "type": "string", "description": "Required benefits"},
{"name": "equity_vehicle", "type": "string", "description": "ISO, EMI, VSOP, BSPCE"},
{"name": "registrations_needed", "type": "string", "description": "Gov registrations"},
{"name": "estimated_employer_cost_pct", "type": "number", "description": "% above gross"}
],
"expected_row_count": "1 per role per jurisdiction",
"sort_order": "jurisdiction ascending",
"deduplication_key": "role_title + jurisdiction"
}
| Quality Metric | Minimum Acceptable | Good | Excellent |
|---|---|---|---|
| Classification rationale | Test named per role | Test + factors cited | Attorney-validated per role |
| Registrations completed | Federal/national only | Federal + state/regional | All levels + local |
| Equity plan compliance | Valuation ordered | Valuation complete, plan drafted | Plan approved, grants at FMV |
| Contract completeness | Template used | Template + jurisdiction addenda | Attorney-reviewed per jurisdiction |
| Compliance calendar | Major deadlines only | All recurring deadlines | Automated reminders + backup |
If below minimum: Do not proceed with hiring. Incomplete classification or missing registrations create immediate legal liability. Engage employment attorney or EOR before first hire.
| Error | Likely Cause | Recovery Action |
|---|---|---|
| Worker classified as contractor but fails ABC test Prong B | Work is core to business | Reclassify as employee. Use IRS VCSP for reduced penalties (10% of one year's liability) [src1] |
| 409A valuation expired before option grant | Material event or 12 months elapsed | Obtain new valuation before granting. Backdated grants trigger 20% penalty [src5] |
| IR35 determination challenged by HMRC | Assessment missed control/substitution/mutuality tests | Use HMRC CEST tool, engage IR35 specialist. Tax credit now prevents double taxation (from Apr 2025) [src3] |
| State registration not completed before first payroll | Overlooked multi-state obligation for remote worker | File immediately. Back-pay missed withholding. Most states allow retroactive registration with penalty |
| EMI grant notification missed (92-day window) | Administrative delay after board approval | Grant becomes non-qualifying. Re-grant if possible [src6] |
| EU worker claims employee status under Platform Work Directive | Contractor engagement meets presumption criteria | Review structure against directive. Reclassify proactively or restructure to demonstrate independence [src4] |
| Component | Free Tier | Paid Tier | At Scale (50+) |
|---|---|---|---|
| Classification analysis | DIY with this card ($0) | Attorney ($500-2K/jurisdiction) | Law firm retainer ($5K-15K/yr) |
| US payroll + tax filing | Gusto Simple ($40 + $6/person) | Rippling ($8/person + modules) | ADP/Paylocity (custom) |
| International EOR | N/A | Deel/Remote ($599/employee/mo) | Volume discounts at 10+ |
| 409A valuation (US) | N/A | $2,500-$5,000 | $5,000-$9,000 |
| EMI valuation (UK) | N/A | GBP 500-2,000 | GBP 2,000-5,000 |
| Equity administration | Pulley free (<25 stakeholders) | Carta Launch ($3K/yr) | Carta Growth ($7K+/yr) |
| Total (5 hires, US) | $300-500/mo | $5K-10K setup + $500-1K/mo | N/A |
| Total (5 hires, global) | N/A | $8K-20K setup + $3K-6K/mo | $15K-50K setup |
Startups frequently classify early team members as contractors to save 20-30% on employer costs. If the worker functions as an employee, California penalties range from $5,000-$25,000 per worker, plus back taxes and interest. [src2]
Apply the jurisdiction-specific test honestly. If the role requires employee status, budget for the full cost. Use contractors only for genuinely independent, project-scoped work.
Some startups issue options at a "best guess" price. This exposes every option holder to a 20% penalty tax plus interest under IRC Section 409A. [src5]
Budget $2,500-$5,000 for the valuation. Order 4-6 weeks before planned grants. Renew after any material event or 12-month expiry.
US at-will employment does not exist in most other jurisdictions. UK and EU employees have statutory notice periods, mandatory benefits, and termination protections.
Each country requires its own contract template. EOR providers include compliant contracts. For direct employment, have a local attorney review the template.
Use this recipe when a startup is hiring its first workers in any jurisdiction and needs to ensure classification is correct, registrations are complete, and equity compensation is legally structured. The output feeds into employment contracts, payroll setup, and equity plan administration. This is a foundational compliance step that must be completed before any worker begins.