Hiring Your First Team
Chapter 10

Hiring Your First Team

Your first hires define your company culture, your execution speed, and your burn rate. Every early hire is a bet on a person, not a role.

On option pool sizing

When you raise a priced round, investors will expect an option pool of 10–20% of the post-money cap table. They will typically want this pool created before the round closes — meaning the dilution comes from the founders, not the investors. Understand this mechanic before you negotiate your first term sheet.

Hiring across state lines is a tax on your time

If you are early-stage and want to hire someone in another state, you have two options. Neither is free.

Option one: full-time employee. You now need to register your company as a foreign entity in their state, set up state tax withholding, comply with that state's labor laws, and often handle workers' comp and unemployment insurance separately. Multiply that by every state you hire in.

Option two: contractor. Faster, cheaper, simpler on day one. But the IRS has rules. A contractor controls how and when they do the work. The moment you are setting their hours, requiring specific tools, or treating them like staff, you have created an employee in everything but name. The penalties for getting this wrong are real.

Option three: EOR. An Employer of Record hires the person on their books and leases them back to you. You pay a premium. You skip the multi-state setup. For a single hire in a new state, the math usually works.

The lesson underneath

Every hiring decision has a hidden compliance cost. Factor it in before you make the offer, not after.

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Deel →
Global payroll, contractors, and Employer of Record

Deel acts as your Employer of Record across 150+ countries and all 50 US states. Hire a full-time employee in a state you are not registered in, or a contractor across borders, without setting up a foreign entity, registering for state tax withholding, or untangling local labor law. Deel handles compliant contracts, payroll, benefits, equity for international hires, and contractor classification — turning a multi-week legal project into a same-day onboarding. For a single hire in a new jurisdiction, the EOR premium is almost always cheaper than the time and risk of doing it yourself.

AI prompts

Contractor vs. employee classification
I have a person working with my company under the following arrangement: [hours per week, type of work, how direction is given, whether they have other clients, tools provided]. I am currently paying them as a [1099 contractor / W-2 employee]. Analyze whether this classification is defensible under IRS and [state] state labor law.
Offer letter + equity structure
I want to make a full-time offer to a [role title] joining as an early team member. My current runway is [months] and I can offer a cash salary of [$]. Draft an offer letter and propose an equity grant: appropriate percentage, vesting schedule, cliff, and how to handle the option grant documentation.