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ShippingEasy Delivers Outside the Box

ShippingEasy Delivers Outside the Box

With Her Third Startup, Katie May is Bringing an Australian Shipping Model to Texas

Written by Briana Loeb
Interviewed by Dan Dillard
Photography by Weston Carls

E-commerce has changed the world. Today, 96 percent of Americans shop online, and analysts predict that a quarter of U.S. malls will disappear in the next five years. Merchants such as eBay, Amazon, Etsy, and Walmart online have revolutionized the shopping industry for consumers and retailers. But the sector that has experienced the most change is perhaps logistics—and fulfillment, in particular. 

ShippingEasy is a company in Austin, Texas, that offers web-based solutions for online retailers and e-commerce sellers to help them organize, process, fulfill, ship, and track their orders through multiple carriers. 

ShippingEasy is founder Katie May’s first software-based company and her third start-up in the online sector. May’s journey in the startup world began at SEEK, Australia’s top job search and recruitment site, where she headed marketing and product.

Subsequently, May founded Kidspot, the largest and most successful online resource for mothers in Australia and New Zealand. In 2012, she became the CEO of ShippingEasy in her hometown of Austin, Texas.

Her passion for and belief in the need for a better shipping solution motivated her to raise $6 million in funds and to hand select her staff. After just four years, the firm was acquired by, her largest competitor, for $55 million. 

"I believed the idea, which was an Australian concept, could really work in the U.S. We’re a streamlined, specialized solution for e-commerce marketplaces. We never touch the boxes, it’s just software. The outcome of our solution is a designated label. So whether you want to use USPS, UPS, FedEx, or DHL, all the orders come in, and it's our job to make sure you're getting the best possible rate and that the labels are put on and the box is getting out same day. And there's a lot of automation that essentially streamlines logistics so that you end up with boxes going out faster at the best rate."

It wasn’t all smooth sailing for May. Four months into her new role, she was faced with a potential disaster. "We learned that the software product needed to be completely rebuilt. Needing to completely rebuild and overhaul our beta was quite a challenge, especially since I am not from the software space. But every year grew less and less difficult. That was six years ago. Four years later, having overcome the obstacles we faced, our product got acquired." 


Additional challenges for May came from her marketing and online publishing background, because the product logistics side was very different. "People require a high level of automation, and we have to support unique workflows," says May. "And this is a fast-moving industry." 

Looking back on her three-year building process, May remarked on ways that leadership skills and roles evolved for her. "As we’ve grown, involvement changes. I keep my finger on the pulse, but there’s more padding beneath my finger. I’ve learned so much about people and what makes them successful. Anyone who is founding a business like this needs to be a risk-taker," May says. "They have to be obsessive. They need to be optimistic and know that it’s going to get easier and better. They have to surrender to the challenges and commit to being in it for the long haul. 

"A good idea is important, but a good idea is not enough. Success really comes down to execution. How engaged is your team? How inspired are they? I think checking their morale every morning is far more important than any metrics we review. There is no success without the people." 

May believes that to inspire performance from her team, the spark has to begin at the top. "Every time I’m on my way up in the elevator, I convince myself 'let’s go today!' If I’m bringing it, then everyone else will bring it, and they all matter so much more than me."

May offers three pieces of advice to anyone interested in taking the leap to become an entrepreneur: "You know, the number one piece of advice I would give is get a partner...And sometimes it can be your investor just depending on the relationship with the investor. But someone who really and truly is going to, on your down days, be able to pull an up day out and balance that back out so you persist through the mud. Because there is a lot of that on the way through."

May also stresses the importance of raising capital and keeping investors happy, "Raising capital is never easy, taking other people’s money comes with a massive sense of obligation. But that kick-starts your obsession, which drives success. Your relationship with your investors is crucial."

The third thing that May believes is invaluable is recruitment. "Everything comes back to finding the right people. Investing time in the recruitment process is probably the best thing you can do. A bad hire costs you so much, and a good hire accelerates. It should be the CEO’s top priority, even if it feels like a distraction." 


May’s advice for recruiting in Austin: "The talent in this city is phenomenal. Coming back here from Australia, where we really did have great talent, I’m amazed at the people we can recruit here. Between the University of Texas, places like Capital Factory, and all of these entrepreneurs mentoring the next round of entrepreneurs, it is so easy to succeed. Not to mention the general shift in young people’s mindset that startups are the way to go. I’ve been really grateful for the talent we’ve been able to hire."

ShippingEasy is now a specialized member of the portfolio, creating an exciting new role for May. "A lot of our competitors from a few years ago are now our partners," she says. "Yet we’re still very much independent."

May calls ShippingEasy her obsession; she knows being obsessed is unhealthy but she also recognizes that her constant drive is what has made her successful. These days, motivated by her family, she’s working to compartmentalize some of that drive and to rebalance her life by surrendering some of her obsession. 

"So I have not totally surrendered that by any means, but [I’m starting] to put new rules in place. As my kids got older they were much more aware, because in the old days you could kind of hide it. You gave them a bath, read them a story, they were in bed by 7:30, you have the rest of the night to do what you want. Well then they start staying up, and so they can recognize if you're still on your computer."

Looking forward May says, "This is my last startup. I hope I can remain in the entrepreneurial community, but I’d like to work alongside young leaders, become a mentor or investor, rather than leading them." May adds with a laugh, "Of course I’ve said that before." 

There’s a cycle of evolving consumer behavior and retail innovation drastically changing the economy—and making room for all kinds of new business. Recognizing this and seizing the opportunity, May built ShippingEasy into an award-winning company through her obsessive determination. But she couldn’t have done it alone: Austin provided a rich environment for the start-up, and May’s focus on partnership and recruitment ensured she was surrounded by the talent she needed to succeed. As she looks to the future, she hopes to strike a balance between maintaining the drive that got her to where she is today and surrendering a bit of it to recalibrate her life and direction to focus more on her family and a new opportunity: fostering Austin entrepreneurship and mentoring other young businesses. 

To learn more about founder Katie May’s incredible success and Shipping Easy’s streamlined shipping solutions go to

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