Member since April 2022
Samantha L. Santiago—call her Sam—is an award-winning global Chief Operating Officer, 5x Fortune 500 executive, keynote speaker, and author of her debut book, Hype Girl: The Confidence Playbook You Didn’t Know You Needed. Known for leading high-stakes transformations across health tech, insurance, and private-equity-backed companies, Sam teaches confidence through execution, not motivation. Her work sits at the intersection of leadership, performance, and results, helping people step into roles they don’t yet feel ready for and win anyway.
In Hype Girl, Sam breaks down how confidence is actually built, through action, discipline, and the right people in your corner. It’s a practical playbook for silencing self-doubt, owning ambition, and showing up with conviction in moments that matter most. Whether you’re chasing a promotion, leading a new team, or making a comeback, Hype Girl delivers the mindset and the moves to perform under pressure.
Across her career, Sam has led multi-million-dollar transformations, been featured in The Wall Street Journal as the first executive to deploy robotics in the insurance industry, and earned recognition as a 3x Top Leader in Massachusetts. A first-generation success and first-degree black belt in Krav Maga, Sam brings a corporate-athlete mindset to everything she does, because confidence isn’t a personality trait. It’s a skill. Her tagline, “Make Big Bets” is a reminder for all leaders to bet on themselves.
Writing & Martial Arts.
That I am half robot...well not really, but one way that I beat burnout is to leverage the best available technology to help me manage type 1 diabetes. I have always believed in the art of the possible, fascinated by space, technology and everything in between. When I was diagnosed as a type 1 diabetic at the age of 31, I was at a growing point in my career. Landed an amazing job at Toyota, lived by the beach, and just met the woman who became my wife several years later. It all started the morning I woke up and my eye sight began to fail, its almost as if someone wiped a dirty rag over my eyes and all I could see is blurry sludge. After going to the eye doctor and getting glasses, my eyesight continued to go in and out. I lost a significant amount of weight, weighing in at just over a 100lbs, and had an insatiable thirst. I thought it was normal to walk around with a camel pak full of water. My work performance declined but I didn't ask for help until the moment I passed out. I finally went to the doctors 3 months later and my blood sugar was 524 (nearly 5x higher than a normal person). I should have been in a coma but somehow I made it through. The thought that I would be dependent on insulin for the rest of my life was a dynamic change and shift. I was also told that I had to inject myself with needles every time I wanted to eat. Have you ever tried to do this at a corporate dinner or out with friends. Its uncomfortable and it was a lot to handle but I knew that I needed to lean into the change to be healthy. 1 year later I adopted a brand new technology, the first and only wireless insulin pump and also a continuous glucose monitor that showed my blood sugar on my Apple Watch....whoa! the difference. I proudly wear this technology to show people that technology at its best helps humankind. Today it helps me live a healthier life and manages the risks that comes with diabetes.
I was always a curious kid with a badass kind of attitude. As a first generation college student, I didn't walk into school with a plan. I just wanted to graduate and make myself and parents proud. I was lucky to be surrounded by a university who "saw me" and was invested in me from the start. They helped me realize my natural skills in problem solving and in business. Once I graduated, I took a big bet by joining my first corporate company as a senior administrative assistant. I told my mom that if I just got in the door, I would make it to the top. I worked with the VP to learn as much as I could about the company and took the time to challenge the status quo. Over the next 20 years I took huge leaps in roles and held leadership and executive positions at 5 Fortune 250 companies. As the funnel for women in leadership got smaller, my influence grew. I began to coach other Women to MAKE BIG BETS on their career and then decided to start my own company to help Advance Women In Leadership.
That I am half robot...well not really, but one way that I beat burnout is to leverage the best available technology to help me manage type 1 diabetes. I have always believed in the art of the possible, fascinated by space, technology and everything in between. When I was diagnosed as a type 1 diabetic at the age of 31, I was at a growing point in my career. Landed an amazing job at Toyota, lived by the beach, and just met the woman who became my wife several years later. It all started the morning I woke up and my eye sight began to fail, its almost as if someone wiped a dirty rag over my eyes and all I could see is blurry sludge. After going to the eye doctor and getting glasses, my eyesight continued to go in and out. I lost a significant amount of weight, weighing in at just over a 100lbs, and had an insatiable thirst. I thought it was normal to walk around with a camel pak full of water. My work performance declined but I didn't ask for help until the moment I passed out. I finally went to the doctors 3 months later and my blood sugar was 524 (nearly 5x higher than a normal person). I should have been in a coma but somehow I made it through. The thought that I would be dependent on insulin for the rest of my life was a dynamic change and shift. I was also told that I had to inject myself with needles every time I wanted to eat. Have you ever tried to do this at a corporate dinner or out with friends. Its uncomfortable and it was a lot to handle but I knew that I needed to lean into the change to be healthy. 1 year later I adopted a brand new technology, the first and only wireless insulin pump and also a continuous glucose monitor that showed my blood sugar on my Apple Watch....whoa! the difference. I proudly wear this technology to show people that technology at its best helps humankind. Today it helps me live a healthier life and manages the risks that comes with diabetes.
I was always a curious kid with a badass kind of attitude. As a first generation college student, I didn't walk into school with a plan. I just wanted to graduate and make myself and parents proud. I was lucky to be surrounded by a university who "saw me" and was invested in me from the start. They helped me realize my natural skills in problem solving and in business. Once I graduated, I took a big bet by joining my first corporate company as a senior administrative assistant. I told my mom that if I just got in the door, I would make it to the top. I worked with the VP to learn as much as I could about the company and took the time to challenge the status quo. Over the next 20 years I took huge leaps in roles and held leadership and executive positions at 5 Fortune 250 companies. As the funnel for women in leadership got smaller, my influence grew. I began to coach other Women to MAKE BIG BETS on their career and then decided to start my own company to help Advance Women In Leadership.