WHO ISJAY?

Let me introduce myself a little differently,

Instead of writing another polished cover letter that tries to convince you why I am the perfect candidate for this role, I want to do something a little different. I want to tell you who I am, what drives me, and what I would bring to your team. We spend a huge part of our lives with the people we work with, so I think it matters just as much to understand the person behind the resume as it does to understand their experience.

So, let’s start with Jay. I consider myself a compassionate warrior. That is probably the simplest way I can describe who I try to be every day. We spend a lot of time asking ourselves the complicated question of what we want to do with our lives, but I think there is a simpler question underneath it. Who do we want to be every day? For me, the answer is someone who leads with compassion while fighting for the people, ideas, and things I believe in. I grew up around Providence, Rhode Island. My parents divorced when I was four, and from a young age I often found myself playing the role of the mediator. Looking back, that experience taught me how to communicate, listen, understand different perspectives, and find common ground. Outside of work, I am a cat dad to three cats, an older brother to my sister, and an uncle to an awesome nephew who I strive to be a positive role model for. I love sports (specifically flag football), trying local restaurants because I am a huge foodie, watching anime because I genuinely love the character development, researching and experimenting with technology, personal development, physical health, mental health, meditation, and finding ways to give my time and energy back to my community. One of my favorite things to do is clean trash out of and around local waterways. It may seem small, but I believe small actions matter when enough people are willing to take them.

My resume can tell you what I have done professionally. What it cannot really tell you is that I am a doer. After knee surgery and leaving my position as an assistant service manager, I booked a one way flight to Phnom Penh, Cambodia. I wanted to experience life outside of the United States while challenging myself to grow… While I was there, I taught myself how to code through YouTube and some self paced coding courses. It was challenging, uncomfortable, and one of the most meaningful experiences of my life. It forced me to become more independent, resourceful, and comfortable figuring things out when I did not have someone standing next to me with the answer. When I returned to the United States, I was fortunate enough to join an incredible team at CVS Health. I worked on an initiative focused on bringing our front store application to 100% WCAG compliance so that customers with disabilities could access care without unnecessary barriers. That work meant a lot to me because it was technology being used for something bigger than technology itself. It was about making someone’s experience a little easier. After that initiative, I transitioned into a product role before eventually moving into real estate, where I had the opportunity to support a wide variety of projects, companies, and individuals. I learned a tremendous amount from that chapter of my life, but I always had an itch I could not quite scratch. I missed tech. More importantly, I missed the feeling that I was building something and helping people through it.

That eventually led me back into tech through a Scrum role. When that contract ended, I intentionally took some time to focus on my family, personal growth, and building new skills. During that period, I purchased and renovated a multifamily property myself and moved my mother into the property so I could help care for her while she went through cancer treatment. Thankfully, she is now cancer free. At the same time, I grew as a man emotionally, spiritually and intellectually while becoming deeply immersed in AI.

Over the past year, I have spent a lot of time learning about AI, LLMs, wrappers, automation, voice agents, RAG systems, web development, and the ways these technologies can actually be useful to people and businesses. I have built some projects for myself, worked with clients, consulted with small businesses, and constantly experimented with new tools. I do not consider myself someone who knows everything about AI. Quite honestly, I never will. What I do have though, is an almost insatiable curiosity and a willingness to learn. I love taking something I do not understand, figuring out how it works, experimenting with it, breaking it, fixing it, and eventually finding a way to make it useful… That is a big part of why WHOOP excites me. I am not approaching WHOOP as a complete outsider. I am already a WHOOP member, and I have personally experienced the value of turning continuous health data into something useful and actionable. There have been moments when I have felt anxious about my heart health and having access to physiological information through WHOOP, specifically the ECG function has helped me feel more informed and at ease. That personal connection is important to me. So if I can contribute to building something that helps even one other person feel more informed, empowered, or confident about their health, then I know that I am doing something meaningful. That brings me right back to my idea of being a compassionate warrior.

I am also really excited by WHOOP’s approach to AI. I do not believe AI should exist simply because it is the newest technology. I believe it should be used thoughtfully to make people’s lives better. My favorite superhero is Spider-Man, and one of the most famous lessons from his story is obviously that with great power comes great responsibility. I think that applies immensely well to AI. We have access to an incredible amount of power and intelligence, more now than ever in human history and I believe we have a responsibility to use it efficiently. I am especially interested in approaches like RAG because they demonstrate that we can build smarter systems without always relying on increasingly massive models to store and process everything. It's exciting to create leaner, more efficient, open-book systems that can retrieve the right information when it is needed rather than trying to make a model memorize the entire universe. That’s not just a technical conversation. It is a conversation about building technology responsibly and thinking about the long-term impact of what we create. That is one of the reasons the opportunity to work on AI at WHOOP is so exciting to me. The focus on healthspan and human performance makes the work feel so important. The opportunity to help make AI coaching more accurate, personalized, and trustworthy is exactly the kind of problem I want to spend my time solving.

I also know I am not the candidate with the longest AI resume or the largest portfolio of accomplishments. There may be people applying who have more direct experience than I do. What I can promise you is that I will show up hungry. I am not afraid to ask questions. I am not afraid to say, “I don’t know.” But I will follow that sentence with, “I’ll get back to you with an answer we can work with”. I bring a lot of positive energy, curiosity, empathy, adaptability, and a genuine desire to help the people around me succeed. I care about the culture I am part of. I care about the people I work with. And I care about building things that actually matter.

If given the opportunity, I would bring my whole self to WHOOP. The technologist, the problem solver, the real estate guy, the former developer, the AI nerd, the foodie, the uncle, the cat dad, the guy who cleans trash out of river banks… off of beaches, and most importantly, the compassionate warrior. I would love the opportunity to learn, contribute, and grow alongside the people building the future of human performance.

Thank you for taking the time to get to know a little bit about Jay.

— Jay