Katie May, 49, had a disaster on her hands.

Katie May, 49, had a disaster on her hands. In August 2012 she had agreed to become the CEO of shipping software company ShippingEasy. A veteran of two startups where she’d honed her skills as a marketer, she thought she had joined a promising venture that just needed to expand sales. But four months after she took the job, her newly hired chief technology officer, Barry Cox, set her straight: “He said, ‘Katie, I honestly think you’re going to have to scrap this product.’” With a beleaguered staff facing a flood of customer complaints, she had to decide whether to shut down the company and return $2 million in investor money.

May was torn. There was plenty of demand for ShippingEasy. Vendors who sold through eBay, Amazon and other websites needed a streamlined way to ship packages for the lowest possible rates. Aiming to capitalize on the rise in ecommerce, ShippingEasy’s founder, Mark Helvadjian, Yahoo’s former product head in Australia, had gotten the company off the ground with $130,000 of his own money in 2011. He hired a development team in Serbia that came up with software that attracted more than 100 customers eager to try the beta version. For funding, he turned to David Gordon, a Sydney investment banker who raised an initial $2 million. The company just needed a boss who could market ShippingEasy worldwide.

Gordon tapped May, an Austin, TX native married to an Australian. She’d been involved in two successful Australian startups. She had been employee No. 12 at SEEK, now the biggest employment website in the Asia Pacific region. In 2005 she founded kidspot, which grew into the largest parenting portal in Australia and New Zealand. Gordon handled kidspot’s sale to News Corp. for $48 million in July 2011, a deal that meant May never needed to work again (she says she owned 60% of the company together with another investor). The sale came at the end of a grueling six years. After she left SEEK, May relocated to her hometown of Austin with her husband and two young children. For six years she commuted to Australia for one week out of every month. She accepted the ShippingEasy job on the condition that the company would move to Austin. “I decided to roll the dice,” she says.

Within weeks she raised an additional $2 million from former investors in kidspot. In Austin, she hired four sales people who made 100 calls a day to potential clients. But as soon as they landed new customers, they were hit with complaints, often multiple calls on a single day from the same person. One of the software’s many flaws: It deluged vendors with up to 30 choices of service on a single package, from USPS expedited priority mail to UPS three-day air. High-volume sellers prefer that those choices be automated. “The software was too clunky and time-consuming,” says May.

Helvadjian had used customer service reps in India who were too far removed from users, says May. With her sales staff overloaded, she wound up on the phone with customers herself. That proved useful. For example, she says an Ohio gun seller named Chad told her he wanted to be able to ship as many as 150 orders at once without having to go through an onerous 10-click process to print each label. “I learned about the process flow he wanted to use,” she says.