What You Can Learn from CEOs Who Carry a Quota

The CEO‑Salesperson Connection

In Chicago last week I sat down with a senior vice‑president of sales from a well‑known manufacturing firm. He laughed when I asked whether the CEO of his company actually made sales calls. “Yeah, he does,” he said, “and he’s disruptive.” The words stuck with me. The idea that a CEO is walking into a sales call sounded absurd until I heard the details of his approach.

In that conversation I learned that a surprisingly high percentage of today’s CEOs began their careers in sales. Estimates put the figure at about 85 percent. That statistic is not a quirky trivia fact; it is a window into the skill set that drives company growth at the highest levels. Salespeople learn how to listen for pain, how to articulate solutions in simple terms, and how to close with confidence. These are the same skills that CEOs use daily when they decide which new product to fund, which partnership to pursue, or which market to enter.

Both groups share a few defining traits. They are concise; they cut to the heart of the matter without getting bogged down in details that only irritate them. They are highly motivated, but more than that they are driven. A top CEO doesn’t just keep a goal in mind; they own it. A top sales leader doesn’t just chase the next quota; they set a new target that others will want to chase. They both exhibit a certain level of boldness: they are willing to take calculated risks, and they are prepared to shake up the status quo if it means reaching a bigger objective.

Imagine the CEO of a manufacturing company on the phone with a prospective supplier. He’s not asking for a discount out of habit; he’s asking for a partnership that will bring a new technology to the line. He’s willing to say “yes” to a bold idea that might appear risky to someone else, but to him it is a potential growth lever. The same person, when speaking to a potential client as a sales executive, would do the same. The difference is only the title on the other end of the line.

It’s important to recognize that “disruptive” in this context is a strategic choice rather than an act of chaos. A disruptive CEO or sales leader will challenge the status quo, but they do so in a calculated way. They look for patterns that no longer work and propose alternatives that bring measurable benefits. They’re not reckless; they’re intentional. They’re the ones who say “next” after a proposal is challenged, not “stop” or “don’t” when a question arises. This relentless pursuit of improvement is what keeps them on top.

When the VP of sales talked about the CEO’s style, he also hinted at how often the CEO would step into the sales process. “He doesn’t just review numbers from a boardroom; he’s on the floor, listening to the challenges that our customers face,” he said. That level of involvement shows that the CEO sees sales as the heartbeat of the business, not just a number on a balance sheet. It signals that the company’s strategy is being shaped by frontline insight, not just by analysts in a glass‑winged office.

These observations reinforce a simple idea: to succeed at the top, you must act like a top salesperson. That means listening intently, offering solutions quickly, and deciding with conviction. It means stepping into a conversation that may feel uncomfortable but is essential to the company’s direction. It also means being bold enough to disrupt the established process when the evidence points to a better way forward.

As I walked away from the meeting, I kept that image in mind: a CEO on a sales call, not as a passive observer but as an active problem solver. That image has since guided how I approach my own conversations with senior leaders. If you want to connect with CEOs or top executives, you need to learn how they operate, and that means adopting the mindset of a top salesperson who is not afraid to disrupt.

Turning Your Sales Pitch Into a CEO‑Level Conversation

Many sales professionals find themselves at a standstill when they reach the boardroom. The conversation often shifts from “what do we need?” to “how much does it cost?” The cost becomes the anchor, and the problem disappears into a budget discussion. The key to moving past that dead‑end is to adopt what I call CEOEBS: Chief Executive Officer Equal Business Stature. This is not about bragging; it’s about approaching the conversation as if you’re on the same level as the decision maker.

CEOEBS means preparing to speak in the language that a CEO uses: metrics that tie to revenue growth, risk mitigations that fit the enterprise’s tolerance, and strategic alignment that reflects the company’s long‑term vision. It means asking questions that reveal the CEO’s underlying concerns, such as “What’s the biggest bottleneck in your supply chain right now?” and following up with a solution that directly addresses that bottleneck. When you frame your idea in terms of the CEO’s priorities, you move the conversation from “features” to “value.”

To practice CEOEBS, start by mapping your product or service to the company’s top line. Identify how it could increase sales, reduce costs, or open a new revenue stream. Draft a one‑page playbook that outlines this impact in numbers. When you meet the CEO, begin the conversation by acknowledging their role: “I understand that expanding market share while keeping margins healthy is a top priority for you.” Then, present your solution as a partnership that aligns with that priority.

Disruption is central to this approach. CEOs thrive on change because it signals progress. When you suggest a new way of doing something, frame it as a low‑risk experiment rather than a wholesale overhaul. For example, propose a pilot program with clear metrics: “We’ll run a 90‑day pilot that tests X, and if the results match Y, we’ll scale it.” By putting the risk under control, you reduce the friction that often blocks new initiatives.

One of the most common pitfalls salespeople encounter is letting the conversation slide back into a transactional mindset. “Sure, I can provide a quote,” you might say, and then the CEO’s question shifts to pricing. This is a cue to pivot. Instead of reciting a price sheet, ask: “If you could eliminate 20 percent of the downtime in your production line, how would that impact your quarterly earnings?” This kind of question gets the CEO to think in terms of outcomes, not costs.

Building CEOEBS also requires developing the habit of speaking directly to the decision maker. Many sales teams rely on the middle manager to filter calls and emails. While that approach is efficient for smaller deals, it dilutes the opportunity for a CEO‑level conversation. Make the first move: call the CEO directly, explain your value proposition in two minutes, and ask if they’re open to a short call. If they decline, ask who in the organization can you talk to that will make the same decision.

When you do get a call, manage the time you have with respect. CEOs are pressed for time. Start by acknowledging that you understand their busy schedule. Then, present a clear, concise agenda: “In the next 10 minutes, I want to show you how our solution can reduce your operating costs by 12 percent.” Keep the conversation focused and end with a call to action: “Let’s schedule a deeper dive with your finance team next week to review the numbers.” This structure respects their time and signals that you’re serious.

Over time, you’ll find that adopting CEOEBS changes the dynamics of every meeting. CEOs will see you not as a vendor but as a strategic partner. They’ll bring the conversation to the executive level because they recognize the value you’re offering. This shift in perception often accelerates the sales cycle and increases volume because you’re no longer fighting for the attention of middle managers but engaging the ultimate decision maker directly.

Remember, the goal isn’t just to close a sale; it’s to build a relationship that lasts. CEOs are more likely to become long‑term partners when they feel they’re in the conversation on equal footing. By using CEOEBS, you remove the hierarchy that traditionally separates salespeople from executives and place both parties in a collaborative space.

Anthony Parinello is the author of the best‑selling book Selling to VITO: The Very Important Top Officer. For additional information on his Sales Success Kits, speeches, and his newest book, call 1-800-777-VITO.