When Do You Actually Become a CEO?

Hello home service operators,

CEO. A title people throw around far too casually.

I’m gonna give you all my thoughts below, but let me lead with this: becoming a true CEO is a staged process, not just a title you claim when you form an LLC.

Think about that as you scan today’s resources…

Today’s Resources

• Big Reputation has a “BIG REPUTATION” as a leading AI-based review management and SEO platform

• Nexstar says good-bye to private equity backed firms

• Could this result in the need for even more trade professionals?

• An inside look at how contractors can cut material costs without sacrificing quality

• Are you actively seeking customer reviews? No? I bet your competitors are (here’s a solution)

• Carrier CEO Dave Gitlin said, “We estimate that industry volumes in August and September will be down in that range, if not worse…” (agree/disagree)

Instant On-Screen Quotes = Instant Leads

Every home service operator dreams of generating “hands-off” leads. Contractor Commerce turns this dream into reality.

With instant on-screen quotes, anyone who visits your website can request a custom quote in 60 seconds or less.

Set it and forget it…until the leads begin to roll in.

In August alone, my company, Wilson Plumbing & Heating, booked and completed seven jobs, worth more than $22k, through Contractor Commerce. And that was a slow month.

That’s $22k+ that we may have otherwise missed out on. And best yet, we didn’t have to do any additional work to secure the leads.

If you’re looking to generate leads on autopilot, Contractor Commerce is a good place to start.

The Journey to Becoming a Real CEO

Everyone loves the title “CEO.” But the reality is you don’t step into that role the day you form an LLC. Becoming a CEO is a progression, and each stage forces you to let go of control, reshape your responsibilities, and trust others to carry the weight of the business.

Step #1: Owner-Operator

This is where I started. I was a plumber on the tools, doing the work myself every day. The plumber fixes pipes, the baker makes bread, the CPA files returns—it’s all the same story. You’re both the technician and the owner, which means you’ve just traded one job for another.

Michael Gerber calls it the “entrepreneurial seizure” in E-Myth Revisited. You love the craft, so you start a business, but then you realize running a business has very little to do with the work itself. Ownership feels real, but the business is 100% dependent on your effort. That’s what pushes you into the next stage.

Step #2: Manager of Workers

Growth forced me to hire help. The daily tasks shifted to employees, and my role became managing the people who did the work. This is one of the hardest stages to leave.

I went through the same identity crisis that most owners face. Do I stay in the field because that’s what I’m good at, or do I move fully into management? The pitfall here isn’t money—it’s mindset. To move forward, I had to stop thinking like a technician and start acting like a leader. Until you make that shift, you’re stuck bouncing between both worlds.

Step #3: Manager of Managers

As my team grew, the business needed real infrastructure. I added office staff, call takers, bookkeepers, and frontline managers. These roles didn’t directly produce revenue, so the financial strain was real.

This stage is what I call “owner’s hell.” Rent, managers, software, and overhead all pile up, but the payoff doesn’t come quickly. In trades, this phase can last from $2–3 million in revenue all the way to $15 million. It’s a grind, but the grind is the point. You’re replicating functions, hiring more managers, and building the structure that makes scale possible.

Step #4: Leader of Leaders

Eventually, I wasn’t managing frontline staff or even their managers—I was leading senior leaders who oversaw entire functions like operations, finance, marketing, and HR. My job became aligning those leaders and setting the vision.

This was the first time I really felt like a CEO. At 150–160 employees, I had multiple layers of managers and directors reporting up through the org chart. I wasn’t close to the call center or the sale anymore, which slowed things down. But I realized that if something was too slow, it usually meant we didn’t have a process for it—not that my people were wrong. At this level, speed only comes from trust, process, and buy-in.

Looking Ahead: Stage #5

I’m not there yet, but the next stage is clear: multi-location and multi-state growth. That’s where reporting structures matter even more, and leadership depth becomes the only way forward. I like to compare it to steering a cruise ship instead of a speedboat. Everything takes longer to turn, but the impact is much bigger.

For me, the lesson has been simple: CEO isn’t a title you claim. It’s a role you grow into. Each stage demands that you step back further from the work, trust more of your team, and keep leveling up your leadership.

Ready to take the leap? Watch this podcast episode.

Fuel the Growth Fire With Customer Reviews

Be honest: how many hours do you spend managing the customer review process?

Regardless of the answer, Big Reputation can step in to make review management effortless. Here’s how:

• Connect your CRM (Jobber, ServiceTitan, Housecall Pro)

• Trigger automated review requests the moment a job closes

• Send follow-ups that drive more responses

• Let AI craft smart, time-saving replies

Set it once. Watch the reviews roll in.

OAO readers never pay a setup fee and get their first month free.

Those are the steps every business owner must take to truly become a CEO. It can be a long journey full of twists and turns, but don’t let that deter you. Stay the course.

👊 John

Disclosure: Some of the content and links in this newsletter are sponsored or affiliate links, which means we may receive payment or earn a commission if you click through or purchase. However, all opinions expressed are entirely my own.

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