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How To Engage With The CCO

March 9, 2023

Post 4 of 4 in the Startup Series for CCOs.

You can engage with each person on the executive team one-on-one to understand their issues and challenges, but I’ve found it far more productive to engage with the CCO offsite and with customers. This leads to a better understanding of the service organization than any other meeting time. I have typically spent the most time with or gotten the most value out of CCOs over the years with a couple specific strategies.

In-person meetings with “canary in the coal mine” customers can offer incredible insights. They don’t use canaries in coal mines anymore, but the same principle applies to companies: What are the early warning signs of big problems looming? The earlier you discover those problems the better, and the CCO is usually the first person to figure out something isn’t right with your product or service. I always find the largest clients, the most demanding ones, the ones who push you around, the ones who are highly critical of you, are the ones who make your company a better company. At Return Path, we had those types of clients over the years, from eBay, to DoubleClick, to Microsoft, to Groupon, to Facebook, to Bank of America—and that’s just the short list off the top of my mind. The demanding customer is the one who breaks things and forces you to own up to your lack of scalability. They also either take you to task or threaten to pull their business if you don’t clean up your act. As painful as some of those meetings are, they’re also ones I always wanted to attend in person with my CCO, both so I could eat whatever form of crow needed to be eaten as the Chief Crow Eater (which sends a very powerful message to the customer), and also because the CCO and I could experience the chirping of the canary in the coal mine and learn from the experience together.

While it’s important to engage with the CCO in the critical meetings with demanding customers, it’s also important to understand the base. There’s an old saying from the hardware world that goes, “God was able to create the world in only 7 days because God didn’t have an installed base.” The new world of Internet technologies, SaaS, and agile development is one where your installed base of customers is your biggest asset, not a millstone around your neck. Some of the most meaningful experiences I had over the years with our CCOs were in market, spending time with all kinds of customers together in small groups and large, deeply understanding their needs and use of our product.

The CCO role is easy to ignore or put on the back burner if things are going smoothly at your company, but as CEO I feel it’s best to stay close to the market. Engaging with demanding customers and with the base alongside your CCO is a good way to understand your company and CCO better.

-Matt Blumberg, March 9, 2023.