How Chris Kowalewski, CGO of Compass Group, Sells: Putting People First

Pop quiz: Are you familiar with the Compass Group? If not, let me introduce you. It’s a global leader in food and support services, operating in 35 countries, employing and engaging over 550,000 people worldwide, and serving an astounding 5.5 billion meals annually. In short, Compass Group is enormous and rapidly growing.

Now, would you like to meet the sales leader spearheading this impressive growth? Allow me to introduce you to Chris Kowalewski, Chief Growth Officer (CGO) at Compass Group. Over his remarkable 36-year career with the company, Chris has risen from a regional sales manager to CGO—driving significant success along the way—which makes his journey fascinating.

I had the distinct pleasure of chatting with him about a wide range of topics, but one core theme threads through the entire discussion—his laser focus on people including his team, his customers, and everyone who the organization serves. Everything that he does is in service of a people-first approach. Even as his team adopts AI technologies to assist throughout the entire sales process, its usage is all about making everyone’s job easier so they can deliver greater impact. Oh, and he even shares some great book recommendations!

Without further ado, let’s dive into our conversation.

1. Needless to say, 36 years in sales is an epic run. What do you love most about it and how does it continue to fuel you?

It’s the competitiveness that drives me. My motivation has always come from a need, a desire to be the best at whatever I pursue.

Growing up, I never imagined I’d end up in sales. I started out with aspirations in aeronautical engineering, then aimed to fly rockets. I pursued aerospace engineering but, truth be told, rocket science was a challenge. So, I switched to economics and eventually found my way into sales.

Even as a child in rural Pennsylvania, I was fiercely competitive. I believe that competitiveness is a crucial trait for succeeding in sales at the highest levels. You need to be competitive, resilient, and steadfast in your standards. There’s no room for compromise if you want to truly succeed. It requires a high degree of character and integrity. After 36 years in the field, I've learned that integrity is non-negotiable. 

What I love most about this role is the impact you can have on people's lives. In sales leadership, the real reward is seeing the positive changes you can make. We have countless examples of how our efforts have transformed lives within our organization. That’s the cool part.

For me, sales has never been about transactions—it can’t be. It’s about making a difference, and I truly value leading with an understanding of how our actions affect people. That’s the essence of what I do.

2. What's your sales philosophy that has led to your success?

There are three principles that guide everything I do, from a sales leadership perspective.

First, focus on what you can control: your attitude and your effort. You determine whether today will be a good day or not. No one else can make that decision for you.

Second, be neurotic about preparation and details. There's no winging it in sales if you want to be successful. Every detail matters and preparation is key.

Finally, on a personal note, I don’t expect perfection—it’s unrealistic and unfair. What matters is preparing to the absolute best of our abilities and owning our efforts without making excuses.

3. You and your team have driven exponential growth at Compass Group. Inquiring minds want to know. How did you do it from an operational and talent perspective?

From the very start, it was clear to me that our people are the cornerstone of our success. Our operating partners—those who work with us daily to sell new business and grow Compass—are world-class at executing our clients’ objectives every single day.

I often get asked, both internally and externally, about our "secret sauce"—a term I’m not particularly fond of. I always say there isn’t one. There’s no secret.

The key to our team’s success is retaining our talent within the Compass family. I’ve worked hard to simplify processes and build out support functions to lighten the workload for our field sellers. This allows them to focus on what they do best: being in front of clients.

My role is to remove roadblocks and make it easier for our team to succeed. Selling is tough, and winning is even tougher. They make the difficult work seem easy thanks to their immense talent and the unparalleled support from our creative, finance, and sales enablement teams. For example, we make sure that no one is left crafting their own proposals or presentations; we’ve got experts handling those details.

Finally, I’m surrounded by the best sales leadership team. They are the architects of one of the greatest sales organizations on the planet. In my experience, no one person can see the whole picture alone. My direct reports excel at collaborating and driving unprecedented growth for us at Compass.

4. Retention is such an interesting answer. I’m curious, so let’s do a double click. Tell us a little more about your approach to retaining both customers and talent?

We excel at retaining our clients, boasting a retention rate of over 97%. Our operating teams execute flawlessly, ensuring that, despite serving millions of meals daily across North America and being the sixth-largest employer in the U.S., everything runs smoothly. This high level of execution is crucial for our success.

Client retention is important but to me the only way you get there is if you retain your talent. Across our enterprise, we must excel at this, and I'm particularly focused on it within my organization. 

High turnover is detrimental; it hampers momentum and can damage our reputation. 

We’ve worked hard to ensure that our sales organization is recognized as a great place to build a career. Despite being a large, complex company with 28 operating units, each with its own name, we are fundamentally about people and hospitality. Our business is people-centric and you can’t ever forget that.

5. You’ve also led Compass Group through a massive digital transformation. I know that a lot of organizations are doing the same thing right now. What have you learned and what advice do you have for them?

We were fortunate that a few years back, around 2016-2018, we began transitioning towards digital both as a company overall—embracing cashless and other payment and ordering apps—and within our sales organization. This shift was gradual at first, but it accelerated over time. Then, COVID changed everything overnight.

Before the pandemic, we handled about 7,500 to 8,000 proposals annually, with 90% of them being print and only 10% digital. Within a month of the pandemic's onset, that ratio flipped, and now we’re around 70% digital. The pandemic forced everything to go virtual, and we adapted quickly.

During this time, two things set us apart. First, we focused on innovation in the digital space. Rather than merely reacting to changes, we took a proactive approach, investing in virtual training, green screen presentations, and even virtual reality—skills and tools that turned out to be crucial for our future success.

Second, we prioritized listening to our clients and prospects. We didn’t embrace digital just for the sake of it or to chase after shiny new technologies. Our core is hospitality and people, and that must always come first. Technology should support and enhance our operations, making jobs and service methods easier and more convenient. But the human element remains central to everything we do. We use technology to simplify and improve, while never losing sight of the personal interactions that truly matter.

6. On a related note, let’s talk about how you’re approaching AI. Tell us how you’re thinking about it, both from a technology and talent perspective.

Personally, I’m diving into AI coursework through MIT’s online learning, eager to learn as much as I can about this fascinating technology. Generative AI is becoming a major asset in our proposal process with potential clients. We use it to enhance imagery, improve text, develop voiceovers, and even create client videos, all to make our sales collateral stand out.

Our sellers are leveraging AI to summarize opportunity data, get suggestions on next steps based on past success rates, and conduct research. It’s also great for integrating tools that support prospecting, analytics, and outreach wherever it’s practical. AI also helps streamline everyday tasks, like summarizing meeting transcripts, organizing long email threads, and locating resources on shared drives.

However, the human touch remains irreplaceable. We’re focused on using AI to enhance our current processes, improve efficiency, and identify opportunities, not to replace people. There’s no need for anyone to worry about being replaced by technology. At the end of the day, it’s always going to be about people connecting with people, and I don’t see that changing.

7. Switching gears. Sales is stressful, as we all know. Is there something that you think you do outside of work that kind of helps you stay centered and focused and successful in your role?

As I mentioned, I’m diving into AI through online coursework and I’ve been indulging my love for reading, especially in the evenings when I like to unwind. Recently, I read two fascinating books on AI: Prediction Machines and Competing in the Age of AI. Staying curious and continually learning is important to me, and reading is a great way to keep up with industry trends and expand my perspective. I find that asking insightful questions and staying engaged with current affairs helps keep my mind sharp.

Another key aspect of my routine is prioritizing physical movement and rest. My workouts mostly consist of walking. This morning, for instance, I was out walking around 4:45 AM, covering about four to five miles. I also incorporate yoga and stretching into my routine. When I play golf, I almost always walk the course instead of using a cart—unless it’s exceptionally hot or the course is difficult to walk. I prefer older, historic courses where walking is the norm.

I prioritize walking even when I’m traveling. There’s something special about starting the day with a walk in cities like New York, LA, or San Francisco. It’s peaceful to be out early, with the streets quiet and the sun just beginning to rise. This morning ritual helps clear my mind and find some tranquility. 

Golf, too, offers a similar escape for me. While I enjoy the game, what I really cherish is the time to disconnect, get some exercise, soak up the sun, and connect with others. It’s a great way to clear my head, get some vitamin D, and build meaningful relationships.

8. Here comes one of my favorite questions. What was your biggest failure in sales and how did that experience transform you?

As I mentioned, retention is my top priority. When someone leaves our company—whether by their decision or ours—I see it as a failure on our part. That’s on me and the leadership team. No one joins Compass to fail, and I make that clear during the interview process. Organizational turnover deeply concerns me.

I stress to every candidate that they should get all their questions answered before joining our team. They need to come in with their eyes wide open, fully understanding what’s expected. If we part ways in six months to a year, regardless of the reason, it’s a challenge to replace the position. It’s not just about the time, money, and resources—it’s about disrupting someone’s life, which I find unacceptable. I can handle the inconvenience, but I won’t accept turning people’s lives upside down.

This philosophy also extends to our summer interns. On their first day, I tell them that if they don’t see Compass as a potential career choice after graduation, then we’ve failed them during their internship. Everyone deserves the chance to have a meaningful and fulfilling career, and we must uphold our values to ensure that. The leadership team and I are committed to doing the right thing all the time, and it all starts with taking care of our people.

9. Ok, it’s time to wrap up. Looking forward, how do you think B2B sales will evolve in the next 1-2 years and what do other sales leaders need to do now to prepare?

It’s essential to embrace the rapid evolution of technology, particularly AI. I urge everyone to stay informed about the latest tools, as the landscape is changing quickly. However, no matter how advanced technology becomes, the essence of sales will always be about personal connections. We must never underestimate the value of human interaction.

Refine your communication skills—be an exceptional listener, writer, and speaker. These skills will never go out of style, especially in an era where we often communicate through screens and texts. It's crucial to keep honing these abilities.

One thing that surprises me is how few so-called sales experts discuss making things easier for their teams. To me, this is fundamental. Leaders—whether in sales or any other field—should be more team-centric and people-focused, rather than self-centered.

It’s also important for sales leaders to take a long-term view. My leadership philosophy is simple: How do we ensure our sales organization remains sustainable and successful for the next 10, 20, or even 30 years—long after I step aside? I deeply care about the team, and they know this. While I may not be here for the next 30 years, my focus is on streamlining processes and making things easier for everyone, especially our field sellers.

By placing people at the core of what’s important, you set the stage for long-term success. 

Mic drop. From all of us at LinkedIn, we couldn’t agree more. A heartfelt thanks to Chris for sharing his invaluable insights. His principles extend beyond sales and business, offering timeless wisdom that serves as a guide for both professional and personal success.

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