A customer service rep’s unusual route to success

Are there stereotypes that come to mind when you think of a customer service rep? Maybe you envision a nametag, a polo shirt, khaki pants, a headset. Beyond appearances, perhaps you assume a customer service rep is trying to get their foot in the door professionally by starting at the bottom rung of a particular career ladder.

I don’t know anything about the career path model at craigslist, the classified advertisements website, but I do know that it’s rare in any business for the founder and CEO to hand the reins over to someone else and then take on the role of customer service rep.

Craig Newmark founded craigslist in 1995. In 2000, he turned the company over to Jim Buckmaster and became a customer service rep. Buckmaster is still CEO today.

Newmark discussed his career at craigslist, along with how and why he subsequently branched off into philanthropy, on the March 27, 2022, #NYTReadalong. (The segment addressing his insistence on being a “customer service rep” starts at around the 30:00 mark.)

Host Sree Sreenivasan asked Newmark if it was difficult to turn the company over to someone else. Newmark responded that it was hard — “giving up control of my child” — but he recognized that Buckmaster was capable of making hard decisions, something Newmark struggled with.

A customer service rep with an improbable backstory

When he turned the company over to Buckmaster, Newmark the customer service rep became liberated from all management responsibilities, all management authority and all influence. The agreement with Buckmaster required him to leave Buckmaster alone and focus on customer service.

Throughout the interview, Newmark noted several keys to his philosophy:

• Stay committed to the grassroots
• Listen to what people need
• Don’t get distracted
• Remember the value of connecting with your customers

I was on the production side of the #NYTReadalong when Newmark was the guest. Out of 1.5 hours of content, all of which was good, this segment struck a nerve with me. Those tenets of Newmark’s led me to reflect on two customer service scenarios.

Have it your way

A friend’s experiences at a local fast-food place have almost consistently been mediocre. Staff members have rolled their eyes at her just for being audacious enough to place an order, that kind of thing. During a recent visit, my friend had a gift code that had been printed out from a computer. It was legitimate, but relatively uncommon compared to the format gift cards come in these days. My friend was dreading the interaction, anticipating even more eye-rolls.

“But the staff person was fantastic!” my friend said later, elated that the interaction went well. They didn’t know how to process that type of gift code, but they recognized its legitimacy, courteously asked my friend for an extra moment, and got the manager to show them how to do it.

Isn’t it a pleasant surprise to have a customer service rep care enough about the organization they represent that they serve well? It seems to me that this staff member showed up to do more than clock in and out. She cared about the customer experience.

It matters to have walked in the shoes of your customer

I was with the Florida Healthy Kids Corporation for a long time (almost 20 years). We provided health insurance to uninsured children. FHKC covered a few hundred children in one county of Florida when it started, but eventually grew to be a statewide program that covered hundreds of thousands of children. One of my frustrations for quite a few years was that it seemed difficult for customer service reps to empathize with what it felt like to have a child in desperate need of medical care who didn’t have insurance.

For a number of years, our customer service was handled from a Chicago suburb.

Eventually, our contract was rewritten to require the customer service vendor to be located in Florida.

I’ll never forget the first time I was talking to a customer service rep who said, “My child had this program. I understand these parents — their confusion, their frustration and their anxiety.” She was able to relate because she had filled out the same application, received the same correspondence, shared similar experiences at one point.

What about Craig Newmark?

I don’t know exactly what Craig Newmark’s days looked like when he was being a customer service rep for craigslist (I did read that a lot of his work involved dealing with “scammers and spammers.”) Whatever the case, there’s something to be said about giving up the power and prestige of having the CEO title and getting back to the front lines of helping your business succeed.

Your customers are your reality

The fast-food staffer instinctively knew to connect to what her customer needed.

The Healthy Kids customer service rep did more than read from a script; she related one parent to another.

Newmark told Sreenivasan that he has been doing customer service for decades — most of the time he has been an adult. He told “Business Insider” that customer service “anchors me to reality.”

If you’re a senior leader, have you considered spending some time in the customer service chair (or at least talking with your customer service people)?

This type of reality check may be something to put on your list.