Hiring Fundamentals
Learn when to hire, who to hire first, and how to build a foundation for scaling your team.
The Most Important Decisions
Your team is your company. Every hire you make—especially in the early days—will shape your culture, your execution speed, and your ultimate success. Getting hiring right is one of the highest-leverage activities a founder can do.
"The first 10 employees determine the DNA of your company. Choose wisely." — Naval Ravikant
When to Hire
Knowing the right time to expand your team
Signs You're Ready to Hire
Hire When...
- ✓You have product-market fit signals
- ✓Founders are bottleneck to growth
- ✓Revenue or funding to support 12+ months
- ✓Clear role definition exists
- ✓You've done the job yourself first
Don't Hire When...
- ✗You're still searching for PMF
- ✗Hiring just because you raised money
- ✗The role isn't clearly defined
- ✗You've never done the job yourself
- ✗To fix a problem that's really process
The Founder's Rule
Before hiring anyone for a role, do that job yourself for at least a few weeks. This gives you the context to write a good job description, interview effectively, and manage the person once hired. It also helps you determine if you even need the hire.
Who to Hire First
Prioritizing your first key hires
Hire Sequence Framework
Your first hires should fill the biggest gaps in your founding team's capabilities:
Fill Founder Skill Gaps
If founders are technical, often the first hire is someone who can sell or market. If founders are business-focused, often first hire is engineering.
Hire for Your Bottleneck
What's limiting your growth right now? If you can't ship fast enough, hire engineers. If you can't get enough leads, hire marketing. If you can't close deals, hire sales.
Hire Generalists Early
Your first 5-10 hires should be people who can wear multiple hats. Specialists come later when you have clear, narrow needs.
Common First Hires by Stage
Pre-PMF (Hires 1-3)
- • Full-stack engineer (if non-technical founders)
- • Business/ops generalist (if all technical founders)
- • Designer who can code
Post-PMF (Hires 4-10)
- • Head of Growth/Marketing
- • Customer Success Lead
- • First Sales Rep (if B2B)
- • Engineers for scale
Writing Job Descriptions
Creating descriptions that attract the right candidates
Job Description Framework
1. The Hook (Why Join)
Start with what makes your company exciting. What will they build? What impact will they have?
2. The Role (What They'll Do)
3-5 specific responsibilities. Be concrete. "Own customer onboarding from signup to first success."
3. Requirements (Must-Haves)
Keep this list short (3-5 items). Only true must-haves. Skills can be learned, traits often can't.
4. Nice-to-Haves
Bonus qualifications that would be helpful but aren't required.
5. Compensation & Benefits
Be transparent about salary range. List equity, benefits, and perks.
Common Mistakes
Avoid
- • Endless lists of requirements
- • Vague responsibilities ("wear many hats")
- • No salary range
- • Corporate jargon ("synergy", "leverage")
- • Unrealistic expectations
Do
- • Be specific about outcomes
- • Show the mission/impact
- • Include compensation range
- • Use plain language
- • Be honest about stage/challenges
Budgeting for Hires
Understanding the true cost of hiring
Total Cost of Employment
The salary is just the start. Plan for the true fully-loaded cost:
Rule of thumb: Budget 1.2-1.4x the base salary for true cost.
Startup Compensation Mix
Market rate or below
Depends on funding stage
0.1% - 2%+ for early hires
Vesting over 4 years
Growth, impact, learning
Non-financial benefits
Legal Basics
Essential legal foundations for hiring
Essential Documents
Offer Letter
Title, start date, salary, equity (separate grant), at-will status, contingencies.
PIIA (Proprietary Information & Invention Assignment)
Protects company IP. Employee assigns work created on company time to the company.
Equity Agreement
Stock option or restricted stock grant with vesting schedule, exercise price, terms.
Employee Handbook
Policies on PTO, expenses, conduct, harassment prevention, remote work.
Employee vs. Contractor
Employee (W-2)
- • You control how/when they work
- • Ongoing relationship
- • You provide tools/equipment
- • You pay payroll taxes
- • They get benefits
Contractor (1099)
- • They control how/when
- • Project-based work
- • They provide own tools
- • They pay own taxes
- • No benefits required
Misclassification Warning
Calling someone a contractor when they're really an employee can result in significant fines and back taxes. When in doubt, consult an employment lawyer.
Building Your Hiring Process
Creating a structured approach from the start
Standard Process Overview
Application Review
Screen resumes against must-have criteria. Aim for <48hr response.
Recruiter/Founder Screen
15-30 min call. Culture fit, motivation, basic qualifications.
Skills Assessment
Take-home project, technical interview, or work sample.
On-site/Final Round
Deep-dive interviews with team. Test collaboration and culture fit.
References & Decision
Call references. Make decision quickly. Extend offer.
Timeline Best Practices
- •Target 2-3 weeks from application to offer for most roles
- •Respond within 48 hours at every stage—speed wins candidates
- •3-4 total interviews max—respect candidate time
- •Decide within 24-48 hours of final interview
Practice Exercise
Build your hiring foundation:
- 1List your current team's strengths and gaps—what's your biggest bottleneck?
- 2Define your next 3 hires in priority order with justification
- 3Write a job description for your #1 priority hire using the framework
- 4Calculate the fully-loaded cost and ensure you have 12+ months runway
- 5Draft your interview process with timeline for each stage