Jonathan Hay is Senior Vice President of Business Strategy & Analytics for the Boston Red Sox, where he leads the organization’s use of data and analytics to drive business performance and support the club’s broader success. Originally born in Australia, Jonathan moved to Boston with his family at the age of six and grew up immersed in the city’s sports culture.
Jonathan graduated from Harvard University with a degree in economics before beginning his career on Wall Street at Morgan Stanley. There, he ran the firm’s US Inflation Derivatives business, gaining experience in financial markets, analytics, and strategic decision-making. After five years in finance, Jonathan pursued an MBA at the University of Chicago Booth School of Business, determined to transition into the sports industry.
Following graduation, Jonathan joined the Boston Red Sox as a baseball analytics intern, working with renowned statistician Bill James on player performance projection models. After several years contributing to baseball operations, Jonathan moved into the organization’s business side, applying advanced analytics to revenue generation and fan engagement.
Over the past several years, Jonathan has built a multidisciplinary analytics organization spanning data infrastructure, business intelligence, CRM, predictive analytics, artificial intelligence, and machine learning. His team focuses on helping the Red Sox make smarter decisions across ticketing, marketing, and fan experience.
Jonathan is also the proud owner of two World Series rings and continues working to help the organization achieve its next championship.
As a data and AI leader, which traits and skills do you think matter most, and which of those have been most influential for you in your current position?
“One of the most valuable skills I learned during my career is how to communicate complicated concepts in a way that prioritizes listener comprehension and drives impactful decision-making.
“When I was working on Wall Street and learning tons of new and complicated concepts, I used to call my mother in the evening and try to explain to her what I had learned that day. My reasoning was that if I could explain to my mother why mortgages had negative convexity, then I truly understood it myself.
“This skill has been immensely valuable as my career has continued in the data and analytics space. It’s unfair to expect people with very different backgrounds to all speak the same language of data. It is incumbent upon those of us in this space to translate our own findings into the language of the end-user in an effort to push them towards the optimal data-driven solution.
“At the end of the day, nobody cares how accurate or complicated your model is if you can’t push the adoption of the results. The art of communication becomes the key agent that allows for the marriage of quantitative and qualitative decision-making in the business world.”
Reflecting on your career, what is one non-traditional piece of advice (outside of technical skills) you would give to an aspiring data or AI leader aiming for the C-suite?
“Hire people smarter than you! Leadership means hiring great people, putting them in a position to succeed, and supporting them in every possible way. I am extremely fortunate to have a wonderful team around me, and my goal is to make sure I remove all roadblocks to their success.
“I can’t be the expert in everything, so my goal is to be conversational rather than fluent in all topics related to data and analytics. If I can understand the unique challenges that my team members face, I can focus my energies on setting them up for maximum success.”