“5 Things I Wish Someone Told Me Before I Became the CPO at eBay” With RJ Pittman

Don’t just love your company, but also be your toughest critic. Everybody drinks the Kool-Aid at some point in their company or career. Resist the temptation to be the only person who loves the product you created — or you surely will be.
I had the pleasure to interview RJ Pittman. RJ is Chief Product Officer at eBay where he leads design, product, and engineering for eBay’s worldwide commerce experience. RJ is the driving force behind the look, feel, and functionality of the eBay marketplace and is focused on unlocking the full potential of its buyers and sellers.

What is your backstory?

I was 10 years old when I took my first computer programming class. My first brush with entrepreneurship hit me when I was 15. Apple had just introduced the Macintosh that would revolutionize the personal computer, and I found myself writing a business plan to my parents to make the case for such an extraordinary investment, one I knew we couldn’t easily afford. Not once, but three times my plan was turned down. After my third failed pitch, I was told that I finally got the investment because I never stopped asking how to improve my pitch. They bet on me, not the plan. This became a key lesson and something I took with me throughout my career.

The business plan evolved into my first startup — transforming local copy shops into Mac-powered desktop publishers in the mid-80’s. I helped them purchase the right systems, and provided all the consulting services to train the staff and manage their digital publishing business. I loved every minute of it and continued the business all the way through college.

Along the way, I discovered the magic that sits at the intersection of computer science and people — the ability to make a big impact on industries large and small. I knew that this is what I wanted to do.

After grad school, I followed my passion and stayed with this concept to create a number of startups founded on the basic premise of using computer science to simplify the complexity of the still mostly offline world for consumers. Evolving on this path of simplification eventually led me to Google in 2007.

Google’s unique proposal was both compelling and suspicious, “come to Google and build great things, be entrepreneurial with hundreds of millions of users.” I asked myself — was this even remotely realistic for one person in a company that, at the time, had over 11,000 employees? The short answer: yes, and far more than I could have imagined. We were constantly streaming new products, features and ideas into production for a skyrocketing user base. Entrepreneurs have one ultimate goal — drive impact that changes the world. Google accelerated that for me. I supplied the invention, Google supplied brilliant engineers and several hundred million users.

One such invention was Google Music, the company’s first big push into a music service outside of YouTube. The project launch was pivotal moment — dramatically simplifying access to all music at the speed of Google Search. I forged a partnership with Apple iTunes for the launch, which ultimately led me to Apple — giving me a chance to be entrepreneurial again, a chance to reimagine the Apple Online Store omnichannel shopping just as Apple Retail was taking flight, and, finally, a chance to work with Apple’s leadership team, and Steve Jobs. In 30 years, my career had come full circle and what a ride it was.

eBay came into the frame with an opportunity for exponential personal growth and the chance to drive the future of commerce at even greater scale. Nearly 200M buyers and sellers in 190 countries generating nearly $85B in global sales — accelerating my passion, working with great people, and amplifying my purpose, the eBay way. As Chief Product Officer, my role also includes leading global brand and our charitable giving experience platform on eBay. This combination enables us to focus on delivering better end-to-end customer experiences from the R&D stage all the way to the new brand promise. My teams work at the intersection of technology, brand, user experience, deep science and AI to deliver breakthrough commerce experiences for existing and future customers.

Which person or which company do you most admire and why?

I first met Steve Jobs at Whole Foods in Palo Alto, back in 1991. I was working on a music database product pitch for Peter Gabriel, using the NeXT platform and I needed access to his music engineers at NeXT. Somehow, I had the courage to ask him for help while standing nervously in the checkout line behind him. The next morning, I had an email from the lead engineer — he must have been a fellow Peter Gabriel fan. I got to know NeXT, and a year later I was working for NeXT doing developer training selling NeXT workstations in the Stanford bookstore, and Steve couldn’t resist stopping by to gauge customer interest.

After grad school and into my career, I would occasionally email Steve, and surprisingly he often replied. We remained pen pals over the next decade or two, trading barbs on everything from Android (when I was at Google), to One Laptop Per Child, to iTunes and the famed $.99 cent downloadable song.

Fast forward to my first meeting with Steve after I joined Apple. We shared the elevator up to the board room. He was battling his illness, but was undeterred. He was always undeterred. As we rode up, we briefly reminisced about the days at NeXT and chuckled at how fast the time flew by. In my experience, Steve carried a remarkable understanding of the customer mindset, unlike anything I have ever seen. He was so incredibly steeped in all the nuances of his hardware, software, and services stable. At the same, time he could completely detach from it all when it came to the customer and user experience. It was as if none of the rest even existed. I’ve never met a better product manager than Steve. His customer centricity and sensibility were truly a unique part of his DNA.

How have you used your success to bring goodness to the world?

Early on, I framed my career with three key principles — passion, people and purpose. I have found that by starting any personal or professional initiative with purpose has allowed me to create the most meaningful and impactful experiences. Throughout my career, this has led me to organizations on a mission to unlock positive social impact in some way. At Google, we were all working towards organizing the world’s information and making it universally accessible and useful. At Apple, the focus was on building products that our customers would love, and to change the world for the better.

At eBay, I have been able to bring the purpose of my work much closer to the livelihood of people, families, entrepreneurs and businesses around the world — combining technology, brand, and experiences together — to create a global marketplace that provides equal opportunity for everyone. Our vision for commerce is one that is enabled by people, powered by technology and open to everyone. 
 An important factor in my decision to join eBay was the massive potential of its global impact and charitable giving engine. I saw a real chance to amplify eBay’s mission to empower people and create economic opportunity, while creating new avenues of growth for our marketplace. Today, our sellers can designate a percentage of their proceeds to charities. Tomorrow, we envision a world where charitable giving is an integral part of commerce as we know it today.

What are your “5 things I wish someone told me when I first started” and why. (Please share a story or example for each.)

  1. Don’t try to do it all yourself. As a young entrepreneur, our first instinct is to wear all the hats and do whatever it takes to win. While this is noble in theory, it doesn’t scale very far. Building a team smarter, faster, better than you feels threatening and counterintuitive when you are just starting out, but there is nothing better that a leader can do to scale and build a world class product and company.
  2. Failure is essential to success. Ego is the enemy of success. It keeps us from embracing the valuable lessons when things don’t go as planned.
  3. Be part of the solution, not part of the problem. As a young leader, it’s tempting to want to engage in problems head on with the source- because we are so passionate and emotionally attached to our business, product, and ideas. This obscures good judgement, contributes to an unhealthy decision-making culture in your company and will almost certainly produce suboptimal results.
  4. Get real, stay real. Don’t just love your company, but also be your toughest critic. Everybody drinks the Kool-Aid at some point in their company or career. Resist the temptation to be the only person who loves the product you created — or you surely will be.
  5. The people who are crazy enough to think they can change the world, are the ones who do. Don’t be discouraged if your ideas are not always the most popular in the room. You’re not being truly innovative if you aren’t making people uncomfortable with your vision.