On the Virtue of Career Transitions (Part 1 of 2)

Lessons on Advancing Through Non-Linear Professional Paths

My wife Toma is a professional medicinal chemist with a large biotechnology company. She has worked for the same employer for nearly a decade and has climbed the ladder well, gaining deeper wells of knowledge and expertise in her field along the way. This is highly admirable and has worked well for her career and personal life. Along similar lines, I think about my first boss who hired me as a route planning analyst at America West Airlines early on in my career. With the title of “Manager” at the time, Devon May was laser focused on building his career as an executive in the airline industry. A private pilot with an MBA in Aviation Management, I could see how smart, talented, and dedicated Devon was and I was certain that he would go far. Today, nearly 20 years after we worked together, he has catapulted into the role of CFO at American Airlines, the world’s largest airline. To me, this is a prime example of how building experience and a reputation within a specific field can take one to the pinnacle of career success.

I, on the other, was cut from a slightly different cloth. I have had more of what I deem “career ADD.” Until my most recent professional transition into venture capital in 2019 (which I will discuss in Part 2 of this blog), I had been navigating my career by experimenting and scratching different itches of curiosity. I had some idea of what I thought I would like in terms of both industries and job functions. Some of the jobs I have taken didn’t necessarily reflect a linear career path, but as I found, every experience I’ve had has been a valuable one and has made me a more competent business person. Not only that, but each job I’ve taken over the years has actually turned out to be quite serendipitous down the road in one way or another.

Taking a step back, I had an entrepreneurial bug from an early age. I started my first business at age 11, which I grew into my early 20s as a medium fish in the small pond of collectible non-sport trading cards. This led me to enroll at Babson College, my “one and done” early decision choice for college. I figured this would launch me into the entrepreneurial big leagues. But alas, with six figures of student debt upon graduation in the year 2000, I decided it might be wise to take “a real job” where I could gain more working experience.

Fortuitously entering the workforce during the tail end of the first “dot com” boom (aka “bubble”), I secured my first “real” job as the junior in-house M&A analyst at Lycos. For those who may not remember, Lycos was a leader among the first generation of search engine / web portals and was “kind of a big deal” in the words of Ron Burgundy, before Google came along with a vastly superior product and ate everyone else’s lunch. I was excited to have had a chance to hone my analytical skills, knowledge of the digital ecosystem, and very importantly, temporarily relocate overseas to Madrid after Lycos was acquired by Terra Networks, the Internet arm of Spain’s Telefónica.

A marriage not made in heaven, the “dot com bust” meant the writing was on the wall for what became known as “Terra Lycos.” While I explored opportunities in venture capital at the time, I also had a burning desire to explore another childhood passion of mine, commercial aviation. I was an airline nerd from early on and was curious what it would be like to work on the corporate side of the industry. So with that in mind, I decided to see what opportunities might exist in the sector for a still relatively junior professional. Thankfully, timing was good post-9/11 turnaround in 2003 and I landed a dream role at America West Airlines in Tempe, Arizona, where I joined the route planning team. It was incredible to see first hand how America West acquired its much larger competitor US Airways, which later on merged again with the even larger American Airlines. America West CEO Doug Parker became the top dog at American, and the head of America West sales and marketing, Scott Kirby, is today the head honcho at United. A terrific experience (not to mention the employee flight benefits), but after about 2.5 years, I left and decided to get an MBA.

While I wasn’t quite done with airlines yet, my mentality shifted to the business school mindset of going into management consulting to build my resume for the future. McKinsey’s Amsterdam office beckoned and while I certainly had my opportunities there as part of the airline consulting practice, I knew I wasn’t going to stick around for the long haul. A headhunter found me and my next step was in port logistics with APM Terminals (part of the Maersk Group), where the tables flipped and suddenly I became the McKinsey client. My most enduring memory from APM days must have been presenting a business proposal face-to-face to a sitting Prime Minister. Perhaps a once-in-a-lifetime opportunity. Yet even that experience didn’t keep me in the company for very long. After less than two years, I was off to the next adventure.

By this point, I realized that my industry passions were really in travel and digital technology and I wanted to get back to an innovation-focused career. I was fortunate enough to connect with the CEO of Amsterdam-based Booking.com and landed a job there working on strategic projects and eventually starting up a new B2B division that would later be branded as “BookingSuite.” Despite Booking’s astonishing growth and vibrant culture, it was only a couple of years before the entrepreneurial juices started flowing again.

My friend and former colleague from Booking, Javier Suarez, had left the company and was spending time hashing out a plan to reinvent business travel. After some wrangling, he convinced me that if I was ever going to become a true startup founder, now was the time. We lined up our third co-founder, Avi Meir, who had sold his previous company to Booking, and Javier and I packed our belongings to join Avi in Barcelona to start TravelPerk. I left TravelPerk only about a year in when family health issues brought me back home to the US. Since then, I have watched in awe as my co-founders continued the rocketship journey. Today, Avi remains the leader of TravelPerk, which boasts thousands of customers and employees and was most recently valued at $2.7 billion.

Since returning to Boston in 2015, however, I have started life anew both personally and professionally. I have been focused on investing while I’ve started a family over the past several years. This next phase, including my onramp into venture capital, will be the subject of Part 2 of this story of career pivots, to be published in my next blog. Stay tuned!