Hiring your first employee is one of the biggest milestones for any small contractor. Whether you’re running a one-man excavation operation, mowing lawns all summer, or managing septic repairs, the decision to bring on your first teammate can be both exciting and intimidating. You’re not just adding another set of hands-you’re starting to grow a company.
In this guide, we’ll break down how to know when you’re ready to hire your first employee, what to consider before doing it, and how contractors like you have made that leap successfully. You’ll hear real-world insights from fellow business owners in excavation, landscaping, and septic services who’ve already been there.
Why Hiring Your First Employee Is a Milestone
Hiring that first employee marks the moment your business shifts from you to us. For many contractors, it’s a mix of relief and responsibility relief because you can finally share the workload, and responsibility because someone else’s livelihood now depends on your business decisions.
The Shift from Solo Operator to Employer
When you start out solo, every dollar earned is yours. Every mistake is yours too. Hiring your first employee changes that dynamic. You move from doing every task yourself to delegating and managing. For excavation and septic contractors, that can mean freeing up your time from running the skid steer every day to managing jobs, estimates, and growth.
The Benefits of Scaling Up
- You can take on more jobs and avoid turning away opportunities.
- You can focus on higher-value work like estimating, customer relationships, and business development.
- You reduce burnout and open the door for structured growth.
5 Signs It’s Time to Hire Your First Employee
Not sure if it’s time? These are the telltale signs contractors see before bringing on their first hire:
1. You’re Turning Down Work
If your schedule is booked solid and you’re saying no to clients, it’s time to bring someone on.
2. You’re Doing Too Much Admin
Invoicing, estimates, and scheduling eat into your productive hours. An assistant or crew member can help you focus on the field.
3. Your Workdays Never End
If you’re working sunup to sundown and still can’t keep up, that’s a sign your capacity has maxed out.
4. You Have Consistent Cash Flow
A steady pipeline of projects gives you confidence you can afford the payroll.
5. You Have Repeatable Processes
Before you hire, make sure you can train. Document your workflows and standard practices first.
Owner Stories: Real-World Hiring Experiences
We got together with some of our partners to get their perspectives on the main question here, When Should I Consider Hiring Some Help?
Joe Uran – President, Nordic Companies:
When to hire your first employee?
For me, the first sign was when I was simply too busy to keep up, or the quality of the work started slipping. Another big indicator: when more than 50% of my time was spent on things I didn’t enjoy and wasn’t good at. In the early stages, you spend about 90% of your time on the actual product or service. Once you hit capacity there, it’s time to add help.
The hard part is the jump itself. At 100% capacity you assume that hiring someone gets you to 140% capacity – but realistically, with two people, you each end up only 70% busy. That’s why I recommend hiring in a way that keeps the new person 90% busy. That shift frees you up to spend roughly half of your time working on the business rather than in it, and you become the backup instead of the whole production team. That’s where real growth starts.
What kind of work was I turning down or struggling with?
Mostly the core service work — the stuff that fills your days early on. Once that plate is full, you either turn work away or you rush through it. Neither is good. Hiring helped stabilize quality and create capacity for growth.
What would you do differently when recruiting and training?
It’s natural to hire within your circle – family or friends – and sometimes that works. But not everyone should work together, no matter how strong the outside relationship is. Your first employee becomes more like a coworker or partner than a traditional employee. You will spend a lot of time together in good moments and stressful moments. Because of that, personality fit should outweigh skill.
Before hiring, I’d strongly recommend having a clear outline of expectations. Nothing overly detailed or micromanaging – just high-level clarity around what success looks like. This helps both sides: you know what you’re looking for, and they know what they’re responsible for. Then once they’re in the role, give them the room to win and fail in their own way as long as they stay within your guardrails.
Training with your first hire is mostly on the job. They get thrown into the fire a bit, but training still has to happen. Don’t just hand them tasks and walk away. Work alongside them until you’re both confident they can deliver the outcome you need. Focus on safety, the big picture of how to do things, and what a successful result looks like – then let them fill in the blanks. Remember that while they’re learning the job, you’re learning how to manage for the first time. Pay attention to where you’re strong and where you need to improve.
What is one piece of advice you would give someone hiring their first employee?
Hire for personality and culture, not only skill. Don’t micromanage. Accept that mistakes will happen – everyone makes them. If someone is a poor culture fit, move on quickly. If they’re a good fit but slower to learn, invest the time.
Most importantly, hire before you’re absolutely forced to. Fear and ego cause people to hire too late. Recognize your weaknesses early and bring in someone who offsets them. Even your first employee will free up meaningful time and let you redirect your energy to the parts of the business you’re best at.
Luke Eggebraaten – Founder & CEO, Phaser Marketing:
What made you realize it was time to hire your first employee?
For me, it came down to time and opportunity. I was working late nights, doing everything myself, and starting to see that I was holding the business back. When your schedule is maxed and you’re saying no to opportunities just to stay caught up, that’s the signal.
What kind of work were you turning down or struggling to complete on your own?
I wasn’t necessarily turning down clients, but I was missing opportunities to grow. A lot of my time was going to admin work, fulfillment, and managing day to day details instead of leading.
For most contractors, once you’re spending 20 to 30 percent of your week on tasks that don’t directly make money, that’s a good indicator it’s time to delegate. Around 250K to 300K per year in revenue, a solo operator usually hits their limit. Hiring even one person can boost production by 30 to 40 percent and quickly pay for itself.
Would you do anything differently in how you recruited or trained them?
Absolutely. I’d slow down and get more clear about expectations. My first hire was about survival, I just needed help. Looking back, I’d take the time to define what success looked like, create a simple 90 day ramp up plan, and spend more time sharing our “why” behind the work.
Now when we hire, I focus more on alignment and culture. Skills can be taught, but attitude, work ethic, and values matter way more.
What’s one piece of advice you’d give to someone about to hire their first employee?
Don’t wait until you’re drowning, hire a little before you think you’re ready. The first employee shouldn’t just take work off your plate, they should create more space for you to focus on the high value stuff like sales, leadership, and systems.
Make sure the math works first:
• You can cover their pay for 8 to 10 weeks even if work slows.
• You’ll still have at least 25 to 30 percent profit margin.
• They’ll free up 10 to 15 hours of your week.
If you can say yes to that, you’re ready.
“You don’t hire your first employee when you can afford it, you hire them when your opportunity cost outweighs their paycheck.”
Joe Procopio – Owner, ProSeptic:
What made you realize it was time to hire your first employee?
I was wearing too many hats. Between pumping, installations, utility work, estimates, and maintenance calls, there just weren’t enough hours in the day. In order to scale beyond being an owner-operator, we needed to take the next step and bring someone on. It wasn’t just about getting help; it was about creating the capacity to grow the business instead of constantly playing catch-up.
What kind of work were you turning down or struggling to complete on your own?
We started turning down smaller pumping jobs and had to delay excavation projects simply because there weren’t enough hours in the day. The backlog of calls and service requests kept growing, and we knew if we didn’t start building a team, we’d lose customers and momentum. We also recognized that emergencies and maintenance contracts required reliability, and that meant adding people we could trust to handle the work consistently.
Would you do anything differently in how you recruited or trained them?
Absolutely. In the beginning, we hired based on skill alone, thinking experience was the most important factor. What we’ve learned since is that attitude and work ethic matter so much more. You can train someone to run equipment or pump a tank, but you can’t train reliability, communication, or pride in their work.
This is something we’re currently navigating and have seen firsthand. The effects of trusting the wrong people in your business can be costly. This year, we’ve taken a step back to focus on hiring quality over quantity. We’re being intentional
Employee vs. Independent Contractor
It’s tempting to bring on help as a 1099 subcontractor. But before you do, understand the difference.
- W-2 Employee
- You control hours, tools, and methods.
- You handle payroll taxes, insurance, and compliance.
- You control hours, tools, and methods.
- 1099 Contractor
- They control how and when they work.
- You don’t provide benefits or withhold taxes.
- They control how and when they work.
Misclassification can lead to legal and tax issues. When in doubt, talk to your accountant or payroll service before hiring.
Financial Prep Before Hiring
Hiring too soon can hurt your business. Prep your numbers first.
Budget Basics
Account for:
- Base pay or hourly rate
- Payroll taxes (roughly 10–15%)
- Insurance (workers’ comp, liability)
- Training time
Cash Flow Forecast
Review your next 3–6 months of jobs. You want predictable income before you commit to payroll.
Defining the Role
Your first hire should take the most time-consuming, repeatable tasks off your plate. Examples:
- Excavation: Equipment operator, ground laborer
- Landscaping: Crew member, lawn tech, maintenance lead
- Septic: Service assistant, dig helper, installation tech
Be clear on the role and write a job description outlining expectations, tools, and pay structure.
Recruiting and Hiring
Where to Find Good Candidates
- Local trade schools or vocational programs
- Industry-specific Facebook groups or forums
- Employee referrals
Writing a Job Post That Attracts Talent
Use clear, direct language: “We’re a growing landscaping company looking for a reliable crew member ready to learn and grow.” Keep it friendly, professional, and honest about job duties.
Onboarding & Training for Success
The first 90 days are crucial. Make it structured and supportive.
Sample 90-Day Onboarding Plan
- Weeks 1–2: Safety, tools, job shadowing
- Month 1: Independent task handling
- Month 2: Customer interaction and site prep
- Month 3: Performance review and goals
Provide feedback regularly, new hires want to know how they’re doing.
Leadership Transition
You’re no longer just an operator; you’re a leader.
Change Your Mindset
Your job is now to coach, not just complete jobs. Build systems that help your employee succeed.
Build a Team Culture
Even with one other person, you can define your company’s culture: reliability, pride in work, respect for clients.
Common Hiring Mistakes Contractors Make
- Hiring too early without cash flow to support payroll.
- No training plan in place.
- Misclassifying employees as contractors.
- Failing to communicate expectations clearly.
Avoid these by preparing your systems before you hire.
How Hiring Your First Employee Fuels Growth
When you delegate field work, you gain time for:
- Marketing your business
- Training and quality control
- Expanding your service offerings
Hiring is the first step to scaling. If you’re ready to grow your contractor business, partnering with a marketing agency like Phaser Marketing can help you build a pipeline of quality leads to keep your crew busy.
Quick Takeaways
- Hiring your first employee is a turning point toward business growth.
- Plan financially before you commit to payroll.
- Choose between W-2 or 1099 carefully based on control and compliance.
- Onboard intentionally, training and culture matter more than experience.
- Listen to other contractors who’ve done it successfully.
Bringing on your first employee isn’t just about working less, it’s about building something bigger. With planning, patience, and the right people, you can go from a one-person show to a thriving contracting business. And when you’re ready to grow your marketing along with your team, Phaser Marketing is here to help.
FAQs
1. How do I know I’m financially ready to hire my first employee?
You should have at least three months of steady work booked and cash flow that comfortably covers payroll and overhead.
2. Should my first hire be full-time or part-time?
Start part-time if workload fluctuates. Many contractors expand to full-time once they see consistent demand.
3. How do I handle payroll taxes for my first employee?
Use a payroll service or accountant to manage withholdings and reporting. Compliance is key.
4. What’s the best way to find reliable field workers?
Referrals, trade schools, an ads hiring campaign (something we can assist with) and social media groups for your niche often bring better results than job boards.
5. What should I avoid when hiring my first employee?
Avoid rushing the process or hiring friends without clear expectations. Treat it like a business decision, because it is.
Ready to Grow Your Team and Business?
If you’re at the stage where hiring your first employee feels both exciting and overwhelming, Phaser Marketing is here to help. We specialize in helping excavation, landscaping, and septic contractors scale their operations through smart marketing and growth strategies.
👉 Let’s talk about how to grow your crew and your client list.
Schedule a free strategy call with Phaser Marketing today and take the first confident step toward building your dream team.
Written by Colton Krier at Phaser Marketing | Helping contractors grow through digital strategy and authentic storytelling.
Digital Strategy Manager at Phaser