In episode 11 I caught up with Katie about her experience leading ShippingEasy to acquisition agreement with, her thoughts on leadership topics like incentivizing employees, leading from the middle, and not quitting too soon, and her advice for entrepreneurs.

Listen now:

This episode is also available on iTunes and Stitcher Radio.


Katie is the CEO of ShippingEasy – which recently announced it’s agreement to be acquired by for $55M. ShippingEasy provides online retailers and merchants a web-based software to organize, process, fulfill and ship their orders quickly and easily. Before joining ShippingEasy, Katie was the founder and CEO of Kidspot, which under her leadership grew to become largest media company focused on mums in Australia and was successfully acquired by News Corp. She also helped drive one of the most successful internet IPOs in Australia, as the CMO of Seek. And overall, she has deep experience in marketing, product development, and leadership, plus plays an active role as an advisor to a range of early stage ventures.

Show Notes:

  • Shipping Easy go/ no-go decision – original product did not align with market needs. Had to decide whether to start over or just close up shop. So much of your decisions evolve around whether you’re confident that there is a market. We knew there was a tangible market for the concept. Had a great team of leaders, all on board with the decision. Had a few hundred customers who were willing to feed into the designs and the experience. Majority stayed with them because product was a significant improvement.
  • Key learnings from launch to acquisition –
    • “Change is really hard.” If you’re asking them to change what they do, even if we can save them time and money, there is a deterrent there. You have to be willing to invest with people. Sales people would have to stay involved beyond the sale. Learned early that the salesperson shouldn’t be compensated on the initial sale only, need customer to truly adopt it. Added more humans to the equation – now have an onboarding team and an account management team.
    • “Pace is important.” If you can get it done today, get it done today. Everything moves so fast. Have a weekly release cycle which has put a good pace in our business, entire company embraces it.
    • “The banker matters.” You need someone who recognizes the value, is willing to invest along with you. When its time to get an outcome for your shareholder, choosing the banker is just as important as choosing your second executive.
  • Expat Learnings – Lived and worked in Australia nine years. You learn a ton from having to build all new friendships. From a professional sense, you learn that there are completely different working styles. Katie now has a mix of the confident American style mixed with the more reserved Australian style. As you age and mature, you recognize the flexibility needed in leadership – learned a lot of this while abroad. Better at navigating different styles. Her American approach may have made others more confident in her abilities and her recommendations, which likely contributed to her getting a high degree of trust.
  • How she got into Entrepreneurship – Had not planned to be an entrepreneur in advance. With KidSpot, encountered a problem that she wanted to fix – a place to stitch all of her kids’ activities together. Decided to fix the problem herself. Wrote a business plan and did nothing with it for over a year. Eventually decided to pursue it.

Someone has to solve this, I guess it will be me.

  • Kidspot acquisition –  Once they had all the moms in one place, the ad dollars would follow, and then then the other media companies showed interest in the first 18 months. Pursued for five more years but knew an acquisition would likely happen one day. The reason we decided the timing is right is because Facebook came around and the moms started spending time there – we could see this disruption would require them to be something bigger. Being part of a bigger company meant we were going to continue getting media buyers’ meetings.
  • Key leadership learnings

It took me a long time to learn this, someone should benefit from it!

  • Carrot vs. Stick – If there’s a way to put reward in front of someone instead of a penalty, it’s much better. “If we start from a position of ‘is there a way we can turn this into a reward, instead of the opposite?’ we’re probably going to get a better outcome. And the person is going to come into work a lot happier about what it is they are being asked to achieve.”
  • Leading from the middle – Haven’t had an office in years, prefer to sit in the middle of the floor. Can soak the mood of the team, you’re recognizing the ups and downs. She hears every day what is blocking the customer from the sales calls around her. This is a big part of the pace at which we learn and innovate. Same for all leaders at the company. The executive team does not sit together – they are spread throughout the two floors, immersed in different teams.
  • Don’t quit too soon – Sometimes you should stick with something, even if you don’t love it. Started in accounting, which she did not enjoy, but 15-20 years later her accounting background has come in very handy as a CEO. Stayed with it long enough to learn the function well. In another example, she got into a position where she was traveling back and forth to Australia for six years – was not an ideal set up but she is so glad she stuck with it rather than quitting. There’s never a wasted skill. You will leverage it somewhere, somehow.

It’s always fine line – sometimes you have to take your knock and move on… but sometimes you have to take a knock and stick with it. Determining which is which is not easy. Sometimes you could just quit too soon and never seen the fullness of time that opportunity would bring you.


  • Advice – When starting a business
    • Get a partner. It is hard. It will always take longer than you think, cost more. Part of it is bringing another set of skills, but ever moreso you need to prop eachother up when you have hard times. One person will go to deep while the other keeps a broad perspective.
    • Set it up properly from the beginning – no one wants to spend money on legal and accounting. Law firm gave them a “startup pack” – 20 documents you will need when you start a business.. There are often shortcuts like this. Paradigm Capital. You don’t need a lot of money to set it up properly, but DO set it up properly.
    • Need to fully understand the total addressable market – Many just look at ideas that serve their own need, or their immediate market needs, but it will never be a big idea because there’s not a big TAM worth pursuing.