Gusto
Gusto CEO Josh Reeves
He wasn't exactly undercover (his employees knew who he was) but in the course of a couple of months, he shadowed someone on each of the 37 teams in his company and learned their jobs.
It was revelatory, he told Business Insider. He learned things about the way his company worked, and the people who worked there, that he just couldn't see from his perch at the top.
It made him realize he wanted to get to know his customers in an equally personal manner, like the old days, when Gusto was tiny and the soft-spoken, introspective Reeves was the guy doing customer support.
Today, Gusto has 40,000 customers and just over 400 employees between San Francisco and its other main office in Denver.
Meeting all of those customers would be impossible, but Reeves has decided to meet a few of them, particularly ones living in areas that are far from Silicon Valley both in locale and ideology.
So next month, he's renting a Winnebago, firing up a blog and hitting 11 cities in two weeks (the longest road trip of his life, he says). They are: his home town of San Francisco; then onto San Luis Obispo and Pasadena, California; then Phoenix; Albuquerque; Amarillo, Texas; Oklahoma City; Little Rock; Nashville; Mobile, Alabama; and Jacksonville, Florida.
While part of this is clearly a social media stunt, part is a genuine interest in leaving the Blue State tech bubble and talking to business owners in different parts of the country.
"I'll be telling their stories and sharing cool ideas and celebrating folks going the extra mile. For one company in each city we'll donate $1,500 to the charity of their choice as a recognition of how they take care of teams," he says.
For instance, he plans to meet a non-profit in Albuquerque called Paws & Stripes that provides service dogs for military veterans with post-traumatic stress disorder and brain injuries for free. It was founded by Lindsey Stanek when her ex-husband came home suffering from PTSD. It offers its 16 employees full benefits and fun things like Dog Fridays, where they get to bring their own dogs to work.
In Jacksonville, Reeves will hang with Subculture Corsets & Clothing, a retail clothing store and family business that sells pinup, steampunk, and Gothic clothing. This 12-employee company also offers its employees full benefits, he says. Plus, Reeves heard a rumor that it once closed the store, telling employees it was taking them all to a trade show in Orlando, but took them to Disneyland instead.
Winnebago
This is the Winnebago that will house Gusto employees on their road trip
His cofounders Tomer London and Eddie Kim will join parts of the trip as well.
It won't get overly cozy for four to six co-workers in a one bedroom 28-foot RV, he says. He and his chief of staff will sleep in the RV each night while the other two employees, both women, will get motel rooms.
"I hope this can be a rallying cry and more and more tech CEOs do these cross-country trips," he says, noting that it's critical for tech leaders to "get out of Silicon Valley" and meet people in "mainstream" America as well.
"Zuck is doing something similar as well," he adds.
Reeves is referring to Facebook CEO Mark Zuckerberg and his 2017 New Year's resolution to meet someone in every state.
In March, Zuckerberg went on a Red State tour and met with military folks at the world's largest military base, Fort Bragg, North Carolina (and lunched with their spouses). He also raced around a NASCAR track in Charlotte with Dale Earnhardt Jr. and dropped in for a prayer service at a Black church in Charleston, South Carolina, Mother Emanuel, the oldest African Methodist Episcopal church in the South.