Skip to Content

Think Space: Katie May

ShippingEasy's CEO prefers fun and unaffected to formal and fusty

ShippingEasy Katie May

The heavy wooden doors that greet visitors at the third-floor offices of ShippingEasy suggest accounting firm torpor rather than speedy transport of any kind. If the weather (overcast), the building’s exterior (brick), and stale hallway décor (carpet, carpet and more carpet), were any indication, this particular Think Space piece, I thought, will be a somber one.

I’d never before met Katie May, who joined ShippingEasy as CEO in 2012, which she recently sold for a robust $55 million. ShippingEasy helps online sellers ship their orders. Similar to a travel website that makes booking hotels and flights cheaper and easier, ShippingEasy’s software makes shipping cheaper and easier.

Fully prepared for austere lighting, more drab carpeting and a capacious corner office, I was surprised to step into a bright wonderland for, and full of, mostly twenty-somethings. There’s the basketball arcade game and ping pong table. Guitars, yoga balls and a large cutout of a robot named “Jack Ship.” I would have walked back out the doors to find the correct suite had I not spotted our photographer, looking equally perplexed. She is here to shoot a CEO’s formal office. There isn’t one.

Katie May is a young forty-nine. She strides up with an outstretched hand. She offers water and seems to produce it before walking away. May has perfected a professional chic that includes black skinny jeans. She has a warm, unaffected mien, with a tendency to talk at a pace just fast enough to require listening later to our recorded conversation at a slightly slower speed.

ShippingEasy Tribeza Katie May

The only partitioned space in an otherwise open floor plan is a glassed-in conference room. May’s “corner office” is a white IKEA desk, featuring little more than a notepad, a laptop, a coffee mug and a mini-succulent that might very well have been put there for the shoot. The only difference between her desk and that of her young staffers comes down to desktop “stuff.” A quick survey of other work surfaces includes a Nerf gun, three comic books, a dog mug and a set of two-pound weights. There’s a scooter, too. “That scooter goes back and forth all day,” says May. “I can’t image what the people below us think.”

May is opposed to the traditional “ivory tower” office layout with a prominent demarcation—in the form of an actual office—between the boss and everyone else. Her workspace must-haves are intangible. She requires dynamism and personal interactions, so May spends most of her time on the third floor among the sales team. Their job is to make cold calls to companies, large and small, across the state. There is a practical reason for May to embed. “If I am here, I know when someone loses a sale and can ask what the company needed us to be able to do that we can’t do,” she says. “So much of what happens on this floor can actually help to guide the product development.” May is committed to her young sales team, whose job description includes daily rejection. It is largely because of May that the turnover rate is glacial.

Getting to know her staff is a favorite part of her job, which is why company size has become somewhat of a litmus test for how long she stays at any one company. She prefers the nascent stages of a business, nurturing it from idea to an industry trailblazer, like she did with Kidspot, an online resource for parents in Australia, where she lived for ten years. May, who grew up in Houston and went to undergraduate and graduate school at UT Austin, is married to an Aussie, hence the extreme shift in time zones.

Though ShippingEasy now has a new owner, May hasn’t set a departure date. The number of staffers hovers around 60 and her job is to grow the business. The office is moving, but the vibe will remain the same, she says. She points to an oversized trophy that serves as a vase for two Minions. “I think that’s Matt’s, our head of sales. It’s one of his favorite little characters. I think he thinks it cheers people up.” The power of the Minion may be questionable, but the décor, sports equipment and May’s leadership style is clearly working some magic.

Read more from the People Issue | December 2016