DISRUPTING WITH DISCIPLINE: WHAT I WISH I KNEW BEFORE I BECAME A CEO

When I launched Comploy in 2018, I thought becoming a CEO meant expanding on what I was already good at as a career sales guy: moving fast, building momentum and chasing the number. In reality, I quickly learned that the CEO role requires a legitimate mind shift, from being a tactician to guiding as a steward. Along the way, the shift changes your risk tolerance, your relationship to decision-making and your responsibility to people.

Like many of the small and mid-sized businesses we support, my company focuses on growth. We counsel our partners on what we’ve learned firsthand: if you want sustainable scale, it is critical to set a solid foundation from the start. This footing becomes doubly important if you’re planning to take risks and challenge the status quo.

With a company built on solid fundamentals, disrupting with discipline creates the space for scale while maintaining partner and client service, success and trust. In a PEO, where risk management, compliance and livelihoods intersect daily, a CEO’s stewardship needs to be impactful, solid and repeatable.

So, with that in mind, here are five things I wish I’d known before I became a CEO.

1. ENTERPRISE ACCOUNTABILITY MEANS THE DECISIONS STOP WITH YOU

I spent most of my career in sales for large payroll processing companies, where my contributions drove defined outcomes. As a CEO, I still care deeply about results – but it’s not just my behavior driving outcomes. I now carry full enterprise accountability for an entire team whose actions touch compliance, customers, employees and reputation. We all hold ourselves personally accountable to our clients at Comploy, whom we regard as true business partners and whose success is our success.

There are two key ways in which assuming enterprise accountability influences how I lead.

First, I raised the bar for decision-making. The big question now is: “Does this choice make the business stronger a year – or three years – from now?” As a team, we don’t just solve for immediate wins; we embrace opportunities to support the long-term success of our company and our clients.

Second, I learned to rely on the strong, smart, and capable people within my organization by setting clear expectations, stepping back and trusting them to do their jobs. Team trust sounds like a given, but I was amazed at how that particular mindset shift freed up my bandwidth to understand what moves the needle and use it to set our course.

2. HIRE PEOPLE WHO KNOW WHAT YOU DON’T

You can’t scale a company on hustle and instinct alone. Be honest with yourself about what you don’t know, then hire for it. At Comploy, that meant bringing in a COO who is process-driven, disciplined and relentless about building a structure that actually holds up at scale.

This exercise reinforces a principle that I regularly revisit: Don’t hire for cost. Hire for fit. Surround yourself with people who are smarter than you, then listen to them, let them advise and educate you. In any industry with deep-rooted legacy habits, enabling your leaders to rethink the playbook is how you change the game without creating chaos, which leads me to lesson three.

3. FAIL, BUT FAIL FORWARD

Early on, we made an acquisition where the opportunity to build our client roster was real, and the growth looked exciting, but our structure at the time wasn’t ready. Our ambition outpaced our operational backbone because we didn’t have the framework that we do now.

We caught up thanks to our team’s grit and commitment. But the experience showed me where we needed to get stronger. From that point on, we learned to align decisions with what the organization could realistically support, not just what sounded exciting in theory. And that’s the point. There’s nothing wrong with trying and failing – or even just running into headwinds – as long as you don’t make the same mistake twice.

The lesson helped us build a formal acquisition framework to match opportunities with operational readiness, clarify ownership and stress-test capacity before taking on more work. It showed us to treat challenges as data inputs by debriefing the situation, documenting the real drivers and improving the system without placing blame.

4. CALCULATED RISK IS PART OF THE JOB – BUT IT CAN’T BE RECKLESS

Trust your gut, then support it with facts and data. For example, Comploy recently launched a master self-funded healthcare plan. We knew this could be a differentiator to offer our small business partners, but the stakes were high. So, we stayed persistent about knocking on doors and asking hard questions until we felt confident about a plan and a partner who could deliver for our clients.

This approach applies to growth, too: Resist the temptation to chase every opportunity. When you’re clear on where you win, you can take smarter risks, execute better, navigate pitfalls and scale without piling on avoidable complexity.

5. CULTURE IS A STRATEGY, NOT A SLOGAN

We have a simple phrase up in the office at Comploy: “Do great work. Be great people.” It’s a standard I wish I’d learned sooner because it has shaped how we treat clients, how we make decisions and how we show up for each other when things get hard.

It also means investing in our team’s development. How people lead, communicate, and take ownership is the backbone of our clients’ and our success. We hire people who want to be here, who are curious, who care about the mission and who want to keep improving. When people feel trusted and supported, they do better work, and they stay. We want them to stay.

We’ve learned that culture gets stronger when you make growth and learning habitual. Keep the environment human. Read relevant and challenging books, reflect together and apply what fits. Play games, laugh and make it comfortable for people to bring problems forward early.

DISRUPTING WITH DISCIPLINE AND INTENTION

When growth is the goal, making that growth sustainable is key to long-term success. That’s what disrupting with discipline really means, and why it’s important for a CEO to build guardrails for the fast lane. When enterprise accountability, smart hiring, learning from mistakes, taking calculated risks and investing in a people-first culture come together, you can scale with momentum while maintaining trust, service and consistency.

I may not have known these five things before becoming a CEO, but I’m grateful I know them now, and I’m fired up to see where the future takes us.