Keely is an educator with the Pittsfield Public Schools with a focus in Social and Emotional Learning. Having known Jake since they were in diapers and considering him family, she is a deeply committed to sharing and uplifting the foundation’s mission. 

Keely recently achieved her Masters in Elementary Education and passionately advocates for youth every day in her work. She hopes to continue to support those both near and far as well as to continue to spread Jake’s light and legacy for years to come. Win The Day!

Hannah is an ICU nurse and one of Jake’s closest friends. When Jake was in the ICU, Hannah stayed by his side for all five days, offering critical insight and support to the Hescock family through her medical knowledge and compassionate care.

Their friendship began in middle school and remained strong through the years, with Hannah often traveling the country to cheer Jake on during his football career at UCF.

Currently pursuing her doctorate in anesthesiology, Hannah remains an active contributor to the foundation. She is especially passionate about CPR and AED education, driven by the hope that, through greater awareness and preparedness, others facing a situation like Jake’s will have a better chance at survival.

Kenneth Ferris was born and raised in Pittsfield, MA, graduating from Pittsfield High School (’83), Tufts University (’87), and Suffolk Law School (’90).

Since 1992, he has been an attorney at Hashim & Spinola, focusing on family law, real estate, personal injury, and civil litigation.

Active in the community, he serves on Pittsfield’s Mobile Home Rent Control Board and has previously coached youth baseball, soccer, and hockey while serving on boards for youth sports organizations.

A longtime supporter of local athletics, Kenneth has known the Hescock family since Jake’s Little League days and is proud to be part of the Win The Day Foundation.

Kate is a communications executive specializing in commercial real estate and based in New York City. Over the past 20 years, she has represented dozens of not-for-profit and philanthropic organizations in crafting their operational, community engagement, fundraising, public relations, and marketing strategies.

After losing her father to an arrhythmia when she was a teenager, Kate has developed an especially strong passion for supporting and advancing organizations dedicated to heart health. She has had the privilege of growing up with the Hescocks as family. She is inspired daily by Carey and Jeff's commitment to advancing Jake's legacy and carrying out his devotion to helping others.

Kate is a proud Berkshire County native and is honored to serve as Secretary of the Win the Day Foundation.

Founder of the Jake Hescock Win The Day Foundation and proud mother of her late son, Jake

Carey along with her husband Jeff and their youngest son, Luke have made it their mission to keep Jake’s legacy alive by helping other families who have lost a child to Sudden Cardiac Arrest. 

She continually works to raise awareness of SCA, the importance of CPR & AED training, and provide financial assistance to families of athletes who have lost their child from SCA or suffered a cardiac event. 

With help from God, she has turned her pain into her passion to help build a loving network for grieving families. She believes no one should grieve alone. Her love of people, especially her family is what drives her to work hard to raise funds to sustain the foundation. 

Her lifelong commitment is to prevent another family from experiencing the trauma of losing a child from SCA.

Brenda is the Vice President of Community Engagement at MountainOne. She attended local schools: Wahconah Regional High School, Berkshire Community College and holds a bachelor's degree in Business Administration from Southern Vermont College.

Her career has included finance and human resource roles and five years as the Director of Volunteer Engagement at Berkshire United Way.  The one common thread throughout her career has been her deep connection to the community and helping others.

She was a former GE Elfun volunteer (1998-2007) and President of SABIC Volunteers (2007-2014), 1Berkshire YLP Steering Committee member (2008-2016) and Berkshire Leadership Program (BLP) graduate (2007). You can regularly find her volunteering with Central Berkshire Habitat for Humanity, or surrounded by one of her dozens of  nieces and nephews (sibkids).  She passionately advocates for children and equity. 

Since 2023 she has been involved in the Family Resource Center (FRC) Community Care Team assisting Haitian families to integrate into our community.

McKenzie Milton currently serves as the Quarterbacks Coach for the University of Central Florida Knights. A former standout collegiate quarterback, McKenzie played a pivotal role in UCF’s historic undefeated seasons in 2017 and 2018. During his tenure as a player, he demonstrated exceptional leadership and athleticism, including throwing the first collegiate reception to teammate Jake, with whom he shared a close on- and off-field friendship.

After sustaining a career-altering injury, McKenzie demonstrated remarkable resilience and adaptability by continuing his academic and athletic journey at Florida State University. His commitment to the sport, coupled with his ability to lead and mentor, ultimately guided him back to UCF, where he now contributes to the program’s continued success in a coaching capacity.

Off the field, McKenzie is a devoted husband to his wife, Jany, and a proud father to their two sons. He remains a respected figure in the UCF community and a valued teammate, mentor, and friend to many within the program.

Byron is a Certified Public Accountant and Managing Partner at Smith, Watson & Company, LLP, where he has worked since 1998, specializing in auditing, financial reporting, and tax services. A graduate of Stonehill College (BSBA ’96), he is an active member of the AICPA, MSCPA, and Berkshire County Estate Planning Council, as well as a 2000 graduate of the Berkshire Leadership Program.

Deeply committed to his community, Byron has coached youth baseball, basketball, and soccer for decades and currently serves as District Administrator for Massachusetts District 1 Little League. A past president of the North Adams Rotary Club, he now sits on the boards of the Boys & Girls Club of the Berkshires and Berkshire Innovation Center as Treasurer.

A lifelong Berkshire resident, Byron lives in Pittsfield with his wife, Stacie, and enjoys spending time with their four children and two grandchildren.