Ambitious employees are high performers who constantly question the status quo and push for better ways to work. They feel like a “pain in the ass” because they create friction, but they are the ones who expose weaknesses, spark innovation, and ultimately drive growth you cannot reach alone.
Marketing CEO David Williams once described ambitious people as those who relentlessly ask, “Why do we do it this way?” At Merkle, he had an engineer who challenged every process, refused management roles, but consistently landed in the top three most valuable employees. Your version might be a stubborn project manager or a persistent 23‑year‑old intern who keeps calling, texting, and showing up until you give them a chance.
You don’t need a company full of these people—too many creates chaos—but you do need a few who push you out of your comfort zone. The real risk is not the friction they create; it’s the stagnation you get when everyone quietly does what they’re told and no one demands better tools, systems, or standards.
Once a business reaches meaningful scale, Williams argues you must start sharing the upside or your best people will leave. When Merkle passed roughly $20 million in revenue, they began offering employees equity and profit sharing. His rule of thumb: people cannot “think like owners” unless they are actual owners in some form.
The impact was immediate. Before equity, Merkle flew the entire company to a lavish Las Vegas conference at a cost of about $100,000 a year. After employees owned a share of the profits, leaders came back and said, “Maybe we only send a few people and have them teach everyone else.” The travel budget dropped to around $10,000—and the extra $90,000 flowed to the bottom line and into profit pools.
You don’t have to wait for $20 million to start. You can use phantom stock, time‑bound equity that only vests while someone is employed, or a clear profit‑sharing plan tied to role and results. Williams tells the story of a $10 million owner who refused to give two stars 5% each. They left, built a $40 million rival, and ultimately acquired his company—he kept 100% but capped his upside.
Ambitious employees thrive in strong cultures. Williams calls culture the most valuable asset in a company and personally trained every Merkle hire on its 25+ core beliefs, a focus he describes in detail with investors at Tidemark. Culture is not posters on a wall; it is the daily behavior you tolerate and reward.
One practical tool is appointing a “culture czar.” This person—often not the owner—conducts the final interview for every hire and has absolute veto power based solely on cultural fit. The first time you override that veto, you quietly signal that revenue matters more than values, and the culture begins to fray.
But culture only works if people actually know it. Williams once offered $10,000 to anyone at a client company who could write down all five core values from memory. Out of 42 people, including the CEO who wrote them, no one could do it. Contrast that with Disney, whose simple mission “to create happiness” is drilled into every employee through weeks of training before they ever receive a name badge.
Ambitious employees run faster when your systems are clear. Many owners claim to have processes, but very few have them documented deeply enough that a stranger could step in tomorrow and perform the work. Williams estimates that under 5% of companies below $100 million have truly documented processes for every role.
Documentation alone is not enough—you also need training and feedback. A simple exercise is to ask each team member to write their real job description as if they were being promoted and had to hire their replacement. Have them bullet out tasks and rank them from highest to lowest priority. You’ll quickly see where the written role and the lived role have drifted apart.
In one famous scene from The West Wing, the president suddenly loses the good pens he always had in his pocket. No one had documented that his late assistant quietly ordered and placed them every morning. The same thing is happening in your business right now. When you let ambitious people rewrite processes, challenge steps, and expose hidden work, you turn their “pain in the ass” energy into smoother systems and a more valuable company.