All About the First Hire

Business Strategy

In a previous newsletter, we walked through how to hire: building scorecards, setting expectations, and running a process that sets both you and your team up for success.

The response to that piece was awesome; many of you wrote back with the same follow-up question: When should I actually make my first hire?

It’s a great question. Timing your first hire can be the difference between accelerating growth or burdening your business too early. Here’s what to consider.

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Making your first hire.

One of the biggest decisions founders face when growing their team is whether to bring on contractors or employees. Each path has clear tradeoffs. Understanding both sides can help you make the right call for your stage of business.

Contractors

Employees

There are three common triggers for making your first hire.

1. When you’ve hit a ceiling.
If growth has stalled because you lack a skill or capacity that you cannot cover yourself, it may be time. The right hire should unlock forward motion, not just fill hours.

2. When you’re stuck doing low-value work.
Dan Martell’s book Buy Back Your Time reframes hiring as a tool for freedom rather than just delegation.

He argues that many entrepreneurs get trapped working in their business instead of on it because they hold on to repetitive, low-value tasks. The book introduces the “Buyback Rate,” a simple calculation that helps you determine which activities are too expensive for you to be doing with your own time.

If you’re spending your days buried in bookkeeping, scheduling, order fulfillment or customer service, you’re paying the highest price of all, your time.

A first hire who takes over those tasks doesn’t just relieve pressure; they give you back the hours you need to drive growth, close sales, and build the vision only you can see.

3. When a milestone requires it.
Product launches, new sales channels, or major projects often can’t move forward without someone taking full ownership.

At that point, the decision is less about “if” and more about “when.” A well-timed hire ensures the milestone is met without bottlenecking you as the founder.

This goes back to building your business plan, making sure your strategy has strategy.

A simple way to think about hiring is to ask whether the role will pay for itself.

Imagine you want to hire someone for $100,000. If your net margin is 20 percent, then that hire needs to generate at least $500,000 in revenue to break even. And once you add in employment costs—benefits, payroll taxes, and management overhead—the true figure is closer to $600,000.

Every hire should either generate revenue, save enough money to justify their cost, or buy back your time so you can reinvest it into higher-value work.

The first hire should always address the biggest gap preventing you from hitting your next milestone.

For a product business, that might be hiring a production manager, a pattern maker, or someone who can guarantee supply.

For a go-to-market push, it may mean using a sales agent or rep before committing to a full-time salesperson.

For creative founders, it’s often a finance or bookkeeping role that clears the way for you to focus on vision and growth.

The principle is simple: work backwards from the milestone you need to hit and fill the gap that unlocks it.

Hiring isn’t just about taking work off your plate. Done right, it’s a way to scale.

Tie each role to a clear plan: milestones, key performance indicators, and targets that connect directly to growth.

Document your systems and processes before you hire so the new person can slot into structure rather than chaos.

When you’re choosing who to bring on, you can go in one of two directions.

Both approaches work, it depends on your capital, your appetite for risk, your company’s vision and values, and how fast you need outcomes.

Early hires aren’t just employees. They are partners in building your brand.

Look for resourceful people who are comfortable with shifting priorities and who thrive in uncertainty.

They should be problem solvers with an entrepreneurial mindset, able to wear multiple hats and grow with your company. The right hire will not only help you today but will also be able to train and elevate the next wave of your team.

When we were preparing to scale Kitsch Wines, we really wanted to get it right. Hiring was going to be one of the biggest investments we made.

Instead of rushing into job postings or trying to piece together a process ourselves, we hired an HR consultant who specialized in our industry.

It was not a small investment, and not a decision we necessarily wanted to make. I think a lot of people dismiss HR until you have 100 employees, but we decided it was worth the investment in order to get it right the first time.

The consultant helped us create a roadmap of hiring that fit our specific business.

She walked us through which roles needed to come first, how to structure them, and what success would look like once those hires were in place.

She also provided tools that saved us countless hours: ready-to-go job descriptions, interview question templates, and professional performance review forms.

One of the biggest takeaways was how she shifted our approach to interviewing.

Instead of just checking boxes or looking for “right” answers, she taught us the real insights are often discovered from probing - usually the second or third probing question revealed a lot more than the original one.

Looking back, bringing in an HR consultant before making our first critical hires was a decision that saved us money, time, and stress. We understand resources are usually tight and it’s not a possible decision for many, but the point is take this seriously. An early hire can make or break your business and the cost of hiring, training then firing just to do it again has a much greater cost than the consultant’s.

Your first hire is one of the biggest steps in growing your business. The key is to approach it with intention.

Start with contractors until the role becomes core.

Move to employees when the growth case is clear. Run the numbers to make sure the hire pays for itself. Anchor the decision in milestones rather than emotion. And choose people who can grow alongside you.

Hiring done too early can weigh you down. Hiring at the right time can unlock the next stage of your business.

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