Katie May

What were your early years like?
I grew up in Houston, Texas, one of three kids. My dad was an airline pilot and my mom stayed home with us during our early childhood, then worked in retail when we got older. After high school, I decided to get my degree in accounting at the University of Texas at Austin — mostly because I was good at math and I had met an accountant who drove a nice car. I went to work for Arthur Andersen and I became a CPA. Only then, I realized accounting was actually a terrible fit for me.

So how did you transition from accounting to consulting?
I went back to school and got my MBA. When I graduated, Philip Morris hired me for a marketing role in New York, and I stayed there for a few years before moving to Australia, where my husband grew up. In advance of our move, I interviewed with Strategy& (then Booz Allen Hamilton) and I was fortunately hired to work in their Melbourne office.

What was your consulting experience like?
It was pivotal in terms of what I’m able to do today. I always say that my experience at Strategy& was, absolutely and categorically, what best prepared me to be a CEO.

Any specific lessons remain most relevant today?
Structuring — that ability to uncover the “so what,” and to present it in a compelling way — is something I use all the time. As a consultant, you’re often getting in a moving car and trying to change the wheels. You may not know the industry or the company the way the people inside do, but what you can do is help structure their thoughts and their data to isolate the “so what.” That’s a lifelong skill, with so many applications, to remove the noise and enable the strategic thinking. It’s critical to know how to look at disparate moving pieces and see, aha, here are the things that matter and here’s how we can organize it into three buckets. A succinct presentation, that showcases the “so what” of a data set instead of just presenting the chart, is received in such a different way.

Why did you leave?
It was the middle of the dot-com boom and I was curious about all the new companies emerging around me. I also had a young daughter at the time, and the amount of travel as a consultant was increasingly difficult for someone as ambitious as I was. So, when one of the founders of Seek, Andrew Bassat, who’s another Strategy& alum, reached out to me about joining his team, I was intrigued. He kept talking about online classifieds — moving job ads, real estate ads and car ads from newspapers to the Internet. I had no idea that it was going to be the most explosive, profitable growth in the entire dot-com boom, but I knew I trusted Andrew and wanted to learn more. I felt like joining the company was an opportunity I couldn’t pass up, so I left Strategy& to become the chief marketing officer at Seek.

How did you go from CMO of an Australian startup to CEO of your own company, Kidspot?
I loved working at Seek — and I was there for six years, all the way through the IPO, but I wanted to move back to the United States as our children got older. Around that same time, as I was searching for answers to my own parenting questions and needs, I recognized a gap in the market. So, I developed a business plan for a new parenting website called Kidspot, and I presented it to the former chairman of Seek. He offered me $250,000 for 50 percent of the business. And I accepted. In the end, that was probably the worst deal I ever made. But at the time, his initial funding and mentorship helped get Kidspot off the ground. After we launched, for seven years, I commuted once a month from Austin, Texas, to Australia, where the company was based, and eventually sold the company to News Corp. By the time we sold, we had the vast majority of Australian moms using it and there wasn’t a brand targeting moms that didn’t invest its advertising dollars there. That commute was crazy, but in the end, we got a good result, so I think it was worth it.

So after closing your own very successful deal, what drew you back to another startup?
Every meaningful step I’ve taken in my career has happened because of a good working relationship with someone along the way. In this case, the investment banker that closed the Kidspot deal connected me with ShippingEasy, a cloud-based shipping, inventory, and customer marketing platform for e-commerce businesses. Initially I was considering an investment or a board seat but, somehow ended up becoming the CEO and moving the company from Sydney to Austin. We ended up having to rebuild the software from scratch, so it was a bigger challenge than expected.

What’s the best part of your job now?
Mentoring my team. At least 80 percent of my time each day is spent leading, leveraging my own experience, and really digging in to help people see the bigger picture and make good decisions.

What’s your leadership style?
I’m very metric driven and goal driven, but I’m also highly communicative, transparent, and accessible. I sit right next to the sales team on an open floor, and I talk about numbers a lot. I believe that everyone in our entire organization should be super clear on our annual goals, quarterly objectives, and progress against them. We have a “stand-up” every Friday where I share numbers for the week, the month, and the quarter. People come by my desk all day. Even now, as the business matures and we have more than 100 people, I’m in the trenches listening to the customer, recognizing gaps and opportunities. I’m part of the team.

What do you look for when you hire?
Curiosity and smarts. I might ask someone a variation of a case study: How many cars are on the road in America? Or, how many ping-pong balls could fit in this room? I don’t know the answer. I don’t care. I want to see how the person I’m interviewing thinks. Where would her brain go? What would she draw on the whiteboard? In addition to solid experience, I’m looking for people who are driven, energetic, and willing to work hard.

What’s the best career advice you can offer?
Take risks. When an opportunity presents itself, seize it — even if it’s off the beaten track. Sometimes your career path will not follow a straight line. You’ll have to go left to get right, but the slope of that right will be steeper and faster than if you had just gone right.

Of all your accomplishments so far, what makes you proudest?
My ability to deliver results and inspire people to believe in what I’m selling. That’s what gives me the confidence to raise more capital and keeping building businesses.

What traits do you think make you most successful?
Honestly, I think I’m slightly obsessive, and I thrive in chaos. I love it. The more plates I have in the air, the more I feel like I’m achieving. If something’s still bothering me, I’ll wake up at 4 a.m. to crack it or write it or solve it. I think as an entrepreneur, you need to be slightly obsessive — to keep pushing the business until you find a way to make it successful.

Outside work, when and where are you happiest?
Spending time outdoors with my family or meeting friends for a glass of wine. My husband and I have four kids, two from my husband’s first marriage, who are 29 and 27, and two from our marriage, who are 19 and 17. We are all active and enjoy spending time outside. We like to hike, bike, kayak, and spend time together.

Who do you most admire?
My parents, definitely. They spoiled us in love, but not in possessions. They taught us good values and what’s most important in life. In our house, everyone had to work hard. If other people got $10 for allowance, we got 50 cents. So I started working in junior high school, with my own pickle-making business, and I’ve never stopped. Outside of my family, I’ve also always admired Steve Jobs for his work ethic and ability to see around corners — not everything about him, of course, but a few specific things: He was myopically focused. He had a sort of sixth sense about what consumers want. And, he was maniacal about a brand. He matched up the right people with his vision, and he really created beautiful things.

What’s your motto?
Just get it done.

This interview was conducted and edited by Jen Swetzoff, founder of CLOSEUP, a creative content studio in Brooklyn. She was formerly the deputy managing editor at strategy+business magazine.