Jay Jackson
Chairman & CEO
It was a Tuesday morning when the heater broke and blew a circuit. We had employees coming in, work that needed to get done, and half the office had no power. I hopped in the car and went to Home Depot to buy extension cords. An hour later, everyone was back at work.
Was that the most efficient use of a CEO’s time? Some may say no. But the people who worked for me saw that when something needed doing, I didn’t wait around. I fixed the problem.
That’s the principle that’s guided how I’ve built Abacus: nobody is too good to take out the trash.
Why It Matters
The executive who hasn’t touched the product in years starts making decisions based on theory rather than practice. The leader who delegates every uncomfortable conversation doesn’t hear what the team is actually dealing with. You start believing your own story about how things work instead of seeing how they actually work.
This creates problems. Your team notices when you avoid the hard work—the unspoken message is that you don’t need to understand what they deal with. You develop blind spots because you’re not in the weeds where problems fester. I learned QuickBooks not because I’m great at accounting, but because I needed to understand where every dollar went. When telecom rates started creeping up, I was an early adopter of Zoom because I was paying attention to details most CEOs delegate. And maybe worst of all, if the boss won’t do it, why should anyone else? People start optimizing for titles instead of results.
In the early days, I worked 4 AM to 10 PM making client calls. I drove to Costco for monitors because they were cheaper than Best Buy. I negotiated leases, attended job fairs, wrote offer letters. Not because I was the only one who could, but because I needed the team to know that no part of the business was beneath any of us.
Growing vs. Comfort
When I went to Home Depot for extension cords or Costco for monitors, it wasn’t because I’m the best person for those tasks. It was about what it communicates: the work matters more than the hierarchy. Getting it done matters more than looking important.
There’s a motto I’ve carried for years: growth and comfort are mutually exclusive. You can’t build something meaningful while protecting yourself from discomfort. And you can’t ask your team to embrace discomfort if you’re not willing to do the same.
Learning from the Weeds
Most executives did the ground-level work early in their careers. The distance between them and that work isn’t competence—it’s time and memory.
When I started at Abacus, I did everything because the team was much smaller. I built the services, handled carrier calls, learned the systems, regulations, operations, sales, accounting. Not by choice—by necessity.
What I learned: talented people need guidance to create a unified front. You can’t just hire smart people and hope it works. You have to show them what right looks like, earn their respect by proving you understand what they’re facing.
I try to stay connected to that early version of myself—the one who figured things out because there was no alternative. That perspective shapes how I lead today.
What It’s Given Me
Staying connected to the work—not all of it, but enough—has given me three things:
Operational reality. I know what the team faces because I’ve faced it recently enough that it’s still real to me.
Credibility over time. When I personally interviewed candidates, attended job fairs, wrote offers, and trained people beyond their core duties, I was building a culture where details mattered. The little things add up. You can’t beat competition without watching every penny, and you can’t scale if you lose sight of the bottom line chasing growth.
Culture through action. People watch what leaders do, not what they say. The long game means pitching in—especially when it’s unglamorous.
There wasn’t a single part of this business I hadn’t done or wouldn’t do. To me, that attitude is fundamental to successfully and sustainably building a business from the ground up.
Leadership isn’t always about delegating. Sometimes it’s about showing up, getting your hands dirty, and making sure people know you’re in it with them.
