Your First Hire: Equity Basics, Offer Letters, and AI-Assisted Onboarding

Your first hire is the biggest bet you've made so far — bigger than any feature. Get the equity wrong or the expectations fuzzy, and you'll spend months untangling it.

• Decide: contractor (1099), part-time, or full-time — each has different tax/legal weight
• Equity for early hires: typically 0.5-2% with 4-year vesting, 1-year cliff
• Use a standard offer letter template (Clerky, AngelList, Common Paper) — don't freestyle
• Build an onboarding doc in Notion: mission, tools, 30/60/90 goals, who-to-ask
• Use Claude to draft role-specific onboarding plans from your codebase or SOPs

Vesting protects both of you. If your hire leaves after 3 months, they don't walk with 2% of the company forever. It's not stingy — it's standard.

# First-hire offer letter skeleton

Role: {title}
Start date: {date}
Compensation:
  - Base: ${cash}/yr (or ${rate}/hr if contractor)
  - Equity: {pct}% ISO stock options
  - Vesting: 4 years, 1-year cliff, monthly thereafter

Expectations (first 90 days):
  - Days 1-30: {onboarding goals}
  - Days 31-60: {ownership of X}
  - Days 61-90: {first shipped outcome}

Benefits: {PTO, health, equipment stipend}
At-will employment. Offer expires {date + 7 days}.

Review with a lawyer before sending. Seriously.

Good looks like your first hire shipping a real outcome by day 60, understanding their equity without asking you twice, and both of you still excited they joined at month six.