Hiring Your First Employee? Here’s What No One Prepares You For

Landing another big client. Sales steadily increasing. Filling up your calendar. Realizing it’s time for reinforcements.

Hiring your very first employee should feel like popping a bottle of champagne, and in many ways, it does. But along with the celebration comes a whirlwind of “official” tasks that hit you all at once.

W-4s, workers’ comp, payroll tax registrations, offer letters, onboarding checklists, employment policies…the to-do list gets long, fast.

But here’s what no one prepares you for: Hiring isn’t just about finding your ideal teammate. It’s about stepping into leadership and building a system that supports your new hire, and every future one, too.

This isn’t just about “getting help.” It’s the start of your company’s people experience.

So, what should you focus on to get this right?

Here's a few tips.

1. Get Crystal Clear on the Role

What exactly will this new team member be responsible for?

Define what success looks like in their first 90 days.

Are you hiring for skills, for values, for future potential - or a well-balanced mix?

2. Lay Your Compliance Foundations

Before sending that offer letter, take a minute to make sure you’ve covered every base. Ask yourself:

• Are you registered for state and federal payroll taxes? (And local city/county taxes, as required?)

• Do you have the right workers’ compensation insurance, even if your state says it’s optional?

• Have you set up unemployment insurance and disability coverage, if your state requires it?

• Is your offer letter clear, compliant, and up to date with current employment laws?

• Have you properly classified your hire as an employee - not a contractor?

• Do you know if your employee is exempt or non-exempt under the Fair Labor Standards Act (FLSA)? (This affects overtime eligibility.)

• Have you set up a legally compliant payroll system and set your pay frequency?

• Are you ready to complete all required new hire paperwork (including I-9 verification and state new hire reporting)?

• Are you including all mandatory training, from harassment prevention to industry-specific and safety protocols?

• Are your workplace safety policies up to OSHA standards?

• Are you on top of your wage and hour obligations, such as minimum wage, overtime, meal and rest breaks (by federal, state, and local law)?

• What benefits will you offer - health and supplemental insurance, 401(k), PTO, sick leave, holidays?

• Which benefits are you legally required to provide (by federal, state, or local law)?

• Do you have and distribute all required workplace posters and notices?

• Is your employee handbook up to date, with clear expectations, policies, and company values?

• Are you following all federal, state, and local laws, for your business and wherever your employees work, including remote hires?

• Have you set up systems for secure recordkeeping and employee privacy?

If that list feels daunting, you’re not alone! Each step is there to protect you and your new hire and set your business up for sustainable success.

At The Shiftly, we make it easy, taking on the heavy lifting and guiding you every step of the way, so you can focus on growing your business with confidence.

3. Craft an Unforgettable Experience

Your first hire will always be close to the “heart” of your business. The experience you create for them will shape your culture and ripple outward to every person you bring on after.

Support, communication, and onboarding matter, now more than ever.

Here’s the real secret: You don’t have to figure this out solo.

Too many founders wait until something goes sideways to get help. The smartest ones reach out early, building confidence and clarity as they grow, not chaos.

Because how you handle this first hire sets the tone for your team (and your peace of mind) for years to come.

You only get one “first hire.” Make it the start of your momentum, not your stress.

Let’s map your best next step.

• Reach out to us today at team@theshiftly.com. You’ve got this, and you don’t have to do it alone.

• Hiring a team? Check out our Notion onboarding template to streamline every new hire.

• And because founders deserve some love. don’t forget to grab your limited-edition Shiftly merch!