Hiring Your First Employee & Payroll Made Simple

Ready to make the leap from solopreneur to real deal boss? Hiring your first employee is a huge milestone - but let’s be honest, it can also feel like stepping into a whole new world of overwhelm. Don’t worry - we've got you. Let’s break down when it’s the right time to hire and how to handle payroll without losing your mind (or your margins).

When is it time to hire?

You're ready when you’re consistently turning down great work because you simply don’t have the bandwidth. If you’ve been clocking 60+ hour weeks for months and still can’t keep up with demand, it’s time to bring in backup.

But don’t just hire on vibes - check your numbers. Can you confidently cover payroll for at least 6 months, even if business slows down? If the answer is yes, keep reading.

What should your first hire do?

Look at where your time is going. What tasks are taking up hours that someone else could easily handle?
Think admin, customer service, inbox management, scheduling - those recurring time-eaters.

Pro tip: Don’t hire someone to do your zone-of-genius work. Hire to free up your time so you can focus on what actually moves the needle.

Not quite ready to bring on a W-2 employee? Contractors and freelancers can be a great starting point. They offer flexibility without the commitment of payroll, benefits, or navigating employment law.

Okay, you’re hiring - now what about payroll?

Welcome to the world of payroll. (It’s not as scary as it sounds.)

Payroll software is your new best friend, and there are two standouts for small business owners:

• Gusto: Handles tax calculations, payroll tax filings, direct deposit, and even benefits. Super user-friendly with excellent customer support - great for first-time employers.

• QuickBooks Payroll: If you’re already using QuickBooks for your accounting, this one keeps everything under one roof. Seamless integration makes life easier, and you can run payroll right from your accounting dashboard.

Regardless of the tool, you’ll likely need to:

• Set up workers' comp insurance

• Register for state unemployment insurance

• Review your state’s payroll and labor requirements (they vary!)

• Decide if you’re offering any benefits

Keep it consistent & compliant

Set a payroll schedule - most small businesses go with bi-weekly or semi-monthly - and stick to it. Your team needs to know when they’re getting paid, and you need to plan your cash flow around it.

Also: document everything.
Track hours worked, overtime, sick days, vacation time - you get the idea. These records protect both you and your team and will save you major stress come tax time.

Hiring your first employee is a big deal - and the first step toward real growth. Take your time, put the right systems in place, and don’t be afraid to ask for help along the way.

Got questions about payroll or bookkeeping? Send us a message! We’re here to make it all feel way less overwhelming.