From Entrepreneur to CEO: 3 Lessons From Building a Team
Updated: Oct 12
The first meaningful shift from entrepreneur to CEO happens when you stop personally performing every step of the work. This article explains the practical considerations through Digital Executive’s experience.
How Does Your First Hire Change Your Role as a Founder?
The first meaningful shift from entrepreneur to CEO happens when you stop personally performing every step of the work. When I founded Digital Executive, I handled sales, recruiting, interviews, referrals, and onboarding myself.
My first hire, Polar, began conducting initial interviews; later she screened resumes too. By my third hire, I no longer needed to conduct second-round interviews. Hiring a social media manager was another turning point: I brought in an expert who could do something better than I could, rather than merely taking over one of my tasks. Today, our team has grown to more than ten people.
Why Do Relationships Matter More Than Ads for Early B2B Clients?
For an early-stage B2B company, direct relationships can be more valuable than immediately spending on ads. I attended networking events, conferences, and masterminds because I needed to learn how to sell. Those conversations helped me find early clients and build a community of entrepreneurs who still support one another. Advertising may become useful as the business scales, but relationships gave us our start.
How Can HR Systems Help a Growing Company Retain Clients?
I was anti-HR for a long time. Seemed pointless. Then I actually invested in it, and our retention rate blew past everyone else I compare notes with. Our HR person talks to every contractor and every client at least once a week. That constant check-in is how we keep our finger on the business — because past a certain size, you physically can't be everywhere at once. You have to build internal systems that keep things running without you in the room.
The moment it all clicked for me was our first company off-site. Seeing how many people showed up — people our business was actually employing and impacting — that's when I knew I wasn't just running a solo operation anymore. I was a CEO.
What Did Selling Mattresses Teach Me About Leadership?
Before any of this, I sold mattresses at Mattress Firm. Made $130K a year at 21, which nobody ever believes when I tell them. That job funded the runway to start Digital Executive.
The lesson translated directly: it's all about relationships. There are plenty of outsourcing companies bigger than mine. People work with me because they believe I'll get them the best talent — and I genuinely believe that too, because I built the systems myself. I don't staff anyone I wouldn't hire. We don't make money off high turnover. Whether you're selling mattresses or virtual assistants, if you believe in what you're selling and you keep the client's interest ahead of your own, that's what makes the difference.
That's the whole shift, really: from doing the work to building the thing that does the work without you. If you're a founder still stuck doing everything yourself, that first hire is scarier than it should be — but it's the only way through.
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