Boomerang: My Return To PayPal

On Jan 16th 2016 several months after my second sabbatical & the dust from the eBay and PayPal split had settled, I decided to leave PayPal after almost 11 years of employment. It was a very difficult decision for me to leave behind amazing co-workers/mentors and an incredible growing business that connected deeply with my ability to bring my full passion to work. However, after careful consideration I decided to leave, knowing very well that I might return one day.

During my career at PayPal I did very well, racking up amazing learning’s and experiences, but ultimately over time I began to doubt if my success was earned or potentially a result of being there for so long. I also started to feel my learning had become stagnant and I didn’t see an immediate opportunity to change that. So during my second sabbatical I recognized a strong shift toward containers & public cloud and as someone who has done what is now called Cloud Operations (or DevOps) for his entire career (of 20 years) I began to wonder if I needed to pursue learning these skills to remain relevant.

The only thing I prioritize higher than the people I get to work with in my career is making sure I continuously learn so that I remain marketable, valuable, and employable for my families well being.

Thus in a poetic sense, what lead me away from PayPal, now leads me back — a strong opportunity for new learning’s & growth.

And so on Feb 20th 2018, just two years later, I will return to PayPal to continue my life long learning journey. This time my first mission will be creating our public cloud architecture on GCP (Google Cloud Platform). The majority of my public cloud experience to date has been focused on AWS, and so I look forward to becoming a more well rounded public cloud guy with learning’s that GCP & PayPal will provide. But learning isn’t the only motivation of course. And I think it’s important that I summarize some of the other benefits I saw to return to place where I worked for more than a decade.

Culture

As a leader, I am huge on culture because I believe having a non-toxic, supportive and healthy environment let’s your peoples productivity thrive and it is the only way to achieve the audacious goals required in business to truly compete, win and be world class. In my experience, PayPal had a pretty good if not great culture, and it seemed to be getting better day by day toward the end of my first term (Dan Schulman is awesome). Since leaving, I’ve kept in touch with friends, and I’ve kept a pulse on PayPal’s culture and it’s seems it’s gotten even better. By all accounts it has the makings of a great culture or at least a shot at it and this is an extremely rare gem.

Mentors

Having a good corporate culture might be a pre-requisite to having great mentors. I am not sure, but it seems that way to me and I value mentorship deeply, both as a service I provide and one I receive. Once you have experienced true mentorship in your career, when it’s gone it’s the first thing you miss. I had incredible mentors at PayPal (best in my career) who are still there. People like Kyle Towle, Chris McGraw, Brad McWilliams and to a lesser extent by circumstance Sri Shivanada.

Mentors are something to be cherished, they help us become more self-aware, they help steer us when we’re off the path, and they help us set our sights the right targets.

In addition to these leaders there is a long list of potential mentors I interacted with, but didn’t get a chance to study more closely or to solicit directly for their mentorship, but now I have an opportunity to do just that. These are people like Wes Hummel who now leads the larger organization I am returning to as well as Leah Sweet, Dan Torunian, MJ Austin, and Sumesh Ramakrishnan Vadassery. I could not be more excited & inspired to be surrounded by leaders like these again who I deeply admire & respect.

Difficult Challenges

Payments is a difficult business to scale. For starters, you have to give back the correct answer to the “how much money is in my account?” question to prevent double spending and/or your customers from going crazy. You have to do it with the highest regard for security and availability as possible because you are not afforded any brand blemishing, downtime or maintenance windows or you might violate an SLA that impacts your ability to do business in one part of the world or another.

In other words the stakes are high.

Latency? Nope you can’t have any of that either or conversion rates decline and you lose money. With all these constraints you get incredible learning’s on things like what is linearizability, ACID vs. BASE, and CAP Theorem? And you start creating solutions for highly available distributed systems that include global traffic management, high performance caching, layer 7 software based load balancing, messaging bus’s, and CDN’s just to name a few. You also learn software patterns like retry with exponential back-off, circuit breakers, and graceful degradation. The challenges and thus learning’s are endless…and it seems blockchain is around the corner (that’s on the 5 year plan), but I digress.

An Office

I have been very fortunate & spoiled. At PayPal I had the choice to work from home as much or as little as I wanted, but at Symantec I shifted to working exclusively at home (+travel). Well, as I suspected.

Working from home 100% sucks.

It truly does. Maybe it is because I am an extravert, but even for intravert’s the home life distractions are abound. No matter how many sit downs you have with the wife and kids the propinquity factor just kills all logic when your wife or kid(s) are in panic mode. Of course, those panics are generally short lived, but the damage is already done to your focus. I also believe it to be challenging to have work life balance, when you work from home, because the laptop is right there, it’s already out, you didn’t put it in your bag and leave the office, cause your house is the office..It’s right there, it’s available, just pick it up and you are always working. Work life balance is tough, and in this day in age especially in tech we work long hours, but having a mental separation of home and office, I think will be very healthy for my family and I, so this one was HUGE.

Things That Helped Trigger My Brain To Consider Returning

1. My old boss called me when good opportunities came up. Without him, I probably would not have returned or had the opportunity to do so. So it has to start there, good bosses are amazing. I am flattered and honored to have the privilege to return, and he has my most sincere thanks for the opportunity.
2. There is a chart in this article http://research.hackerrank.com/developer-skills/2018/ under “Work-life balance beats perks”. When comparing companies I realized PayPal scored the highest on every category for me.
3. And finally this article taught me what a boomerang was, and planted the seed that grew. http://www.businessinsider.com/linkedin-vp-explains-why-boomerang-employees-are-becoming-the-new-normal-2016-10

Switching jobs is a big step. And going back to a previous employer can be viewed negatively so it can be a difficult decision to make. It might be good or bad depending on your circumstances, but for me I know it’s the right decision at this time. With that I hope I was able to provide valuable insight for anyone considering boomeranging now or in the future. Thanks for reading!

This article was originally published on LinkedIn on Feb 17th, 2018. If you enjoy my content please follow me on LinkedIn and Twitter. Also check out my YouTube channel for video tutorials.