Our Mission
Our mission is twofold: we host community wellness events and sporting activities to fundraise for our Good Neighbor Fund.
SEM promotes health and wellness through sporting events such as road races, bike rides, walks, sports camps, clinics, and tournaments. Our mission is to inspire active lifestyles while fostering community engagement.
All net proceeds from our events directly support our Good Neighbor Fund. This fund will benefit families and organizations in the greater Boston community, through initiatives such as shelter and food assistance, financial aid for medical needs, elderly support services, special needs programs, youth afterschool and educational outreach programs. Through these efforts, we aim to create a healthier, stronger, and more connected community.
Smile Every Mile, Inc. (SEM) operates as a 501c non-profit organization serving Dorchester and Quincy.

Strategic Launch
1
Funding
Host fundraising events to seed our work and kickstart the Good Neighbor Fund
January to June 2025
2
Design & Implementation
Create our wellness models and activities to fuel the Good Neighbor Fund and develop a process for applying to that fund
June to September 2025
3
Distribution
Deploy our first round of Good Neighbor Fund grants to families and organizations based in Quincy and Dorchester
September to November 2025
Meet the Team
The founders and board members of Smile Every Mile

Founder & President
Derek McCleary
Derek is an SVP for TD Bank and has been working in banking and finance for 36 years. He is also a 20+ year coach and life long volunteer. An entrepreneur, he has founded several companies in the sports industry and is passionate about the role sports play in youth development and society as a whole. Derek has five children who have played high school and collegiate soccer and lives in Quincy (OFD).

Board Member
Michelle Cannon
Michelle is an education administration with 20 years experience in strategic, instructional, and program design at public and independent schools as well as educational non-profits, most recently in Boston Public schools. A former high school athlete (and Boston Latin School Athletics Hall of Fame honoree) who has coached in the community, she is a life-long Dorchester resident and lives there with her husband and two children.

Board Member
Rita Bailey
Rita is a Registered Nurse whose past experiences include working as a staff nurse at Brigham and Women’s Hospital and as a school nurse and Coordinator of Health Services at Quincy Public Schools. She was responsible for the Nursing Department and implementing the Health and Wellness Policy for the school district. Rita has run nine marathons and has participated in several triathlons. Rita has since retired and continues to stay active within the community.

Board Member
Christine Bailey
Christine has worked in the healthcare industry for 25 years and is a life long volunteer and a fundraising guru. She is a 4 year board member of Cedar Grove Neighborhood Association and prior president of Saint Brendan’s Parent Guild. She is currently employed at Boston Public Schools in the special education department. She was born and raised in Dorchester, where she lives with her husband, a Boston Police Sargent, and their two children.

Treasurer
Jared McCleary
Jared ran his first Marathon at 19 and is a former division 1 soccer player. He took to coaching after his playing career came to an end, with positions at UMass Amherst and Holy Cross, as well as at the youth level for the NE Revolution, Western MA Pioneers, Strikers United, and Boston Bolts.

Secretary
Shannon McCleary
Shannon's passion knows no bounds, as 4 knee surgeries, 3 new ACLs, a few re-attached MCL, LCL, TCL, and PCL tendons have not been enough to stop her from playing soccer. Her impressive Highschool soccer career, while hindered by injury, still earned her a roster spot on a college soccer team.
She now spends her time yelling at people on zoom meetings and is eager to find a way back into the athletics she loves so much.