Dr. Jaykyri Simpson is the Executive Director of Young Man with a Plan, a holistic mentoring program serving young Black and Latino men “in the middle” across 8 Boston schools. Under Jaykyri’s leadership, YMWAP has grown from a small program serving 30 students to a 501c3 organization serving over 250 students and alumni in a unique mix of in- and after-school mentoring and success planning.

Jaykyri received his B.A. at the University of New England (UNE) where he captained their division-winning basketball team, and his MBA from St. Joseph’s College in Maine. In 2021, Jaykyri earned his doctorate in Educational Leadership from New England College. His dissertation research explored college persistence in Black males. Jaykyri incorporates everything learned through his research into the curriculum for the young men in the program.

Prior to leading YMWAP, Jaykyri launched Project Ochendo at New Mission High School in Boston, where he taught and mentored students of color, helping them improve study skills and grades, and to access and persist at college.  Jaykyri also has a deep connection to sports. He played college basketball for all four years, starting at a small junior college in Texas and transferring to the University of New England (UNE) to finish his collegiate career.  He served as basketball coach for two years at UNE, and as a basketball coach, admissions counselor, and retention coordinator for three years at Mt. Ida College. In addition to coaching on the collegiate level, Dr. Simpson has coached high school football at New Mission High.

Jaykyri was in the 2020 cohort of the Lewis Family Foundation’s Strong Leader Program, TSNE’s 2021 Nonprofit Executive Directors of Color Program, and serves on the EdVestors Racial Equity Task Force since 2022, where he leads teacher dialogues and conducts research on educational topics including engaging men of color in the classroom, creating spaces of belonging, and factors impacting college access and persistence. He was also named a 2021 INP Changemaker, a 2022 SIF Social Innovator, and is a member of the 2024 Nellie Mae Educational Foundation Speakers Bureau.

Jaykyri is a thought leader whose knowledge of youth is frequently sought by educators, funders, and community leaders. He has been a consultant and guest educator at New England College and has presented at The Possible Zone, the Massachusetts Black and Latino Legislative Caucus, Life Science Cares, Social Innovation Forum, Boston Beyond, The Philanthropy Connection, EdVestors, Third Sector New England, and at CT Rise and Teacher Powered Schools conferences. In 2023 The New Commonwealth Fund recognized YMWAP’s deep community impact by inviting the organization to participate as a “trusted partner” in a state-funded maternal health equity public health initiative.

Originally from Cleburne, Texas, Jaykyri is also a founding member of Men on a Mission, a nonprofit in his Texas hometown.

Desmond Kennard is a native of Boston and graduate of Medaille College with a major in Psychology. Des has dedicated his career to youth development. He worked with autistic students in the Boston Public Schools to design and implement life skills and enrichment activities. Des also was a Senior Youth Counselor at Cooper Community Center in Roxbury. Desmond leads program operations and helps YMWAP build career knowledge and pipelines. In 2023, when YMWAP’s achieved 501c3 status, Des expanded his role to include support of financial operations. He is a certified career coach who has participated in EdVestor’s Career Path development program and leads Success Planning for YMWAP students and alumni. Des brings a working knowledge of Spanish to YMWAP. Des is a 2021 INP Changemaker and received the 2022 Light of Dawnn award for his front-line work during the Covid pandemic.

Lenward joined the Young Man with a Plan program staff in 2022 as Assistant Director after serving the organization in a mentoring capacity for over five years. Lenward began working with YMWAP as Codman Academy’s school-based mentor and remained engaged with the program and students even after leaving Codman. His previous employment includes roles as Dean of Students at Uncommon Schools and Wellness Director at Codman Academy. Lenward is also a Real Estate Investor and General Contractor managing 23 rental apartments in New England.  Lenward is also a member of The Omega Psi Phi Fraternity where he serves as current Chapter President and committee chair for the New England region of brothers.  Lenward earned a B.A. in Psychology from UMass Boston, where he played varsity ice hockey for the Beacons until his graduation in 2011. Lenward is still an active member of the Beacon community and give annual to the Ice Hockey Team he once played for.

Justin joined YMWAP in 2022 in a school based mentor role. In 2024 he became a part of our programming staff as a Program Manager, bringing a deep commitment to serving youth and a strong connection to his hometown of Mattapan. Justin was formerly a wellness teacher and basketball coach at Codman Academy. He also worked at Bedford High School as a campus aide and football/basketball coach, demonstrating his dedication to mentoring students through sports and education.

In addition to his work in schools, Justin served as a stabilization case manager at Project Place, a nonprofit organization. There, he taught a stabilization class, helping formerly incarcerated individuals and those struggling with addiction to rebuild their lives. 

Justin earned his B.S. in Counseling Psychology from Johnson and Wales University in 2017 , where he was also the chapter president of his organization Groove Phi Groove Social Fellowship Incorporated for three years. Before attending Johnson and Wales, Justin played varsity football and basketball at Becker College, further showcasing his leadership and teamwork skills. 

Marcia brings over thirty years of experience in corporate and nonprofit program development, consulting, and grant writing to the YMWAP team. She was a member of the team of school leaders and consultants who created YMWAP’s original design and launched the program in 2015. In her current role, Marcia supports advancement and sustainability initiatives and works with the Board. 

Marcia has designed corporate programs to attract, develop and retain top talent at Fidelity, HP, and Corning, Inc, and consulted on the design of leadership development and mentoring programs. She received her B.A. in American Studies from Barnard College, Columbia University (first gen!) and her M.Ed. from the University of Vermont. 

She has been certified as an executive coach from the Center for Creative Leadership and as a writing group leader from the Amherst Writers Program. Outside of YMWAP, Marcia teaches poetry to senior citizens and helps high school students write compelling essays for college applications.

Elo joined Young Man with a Plan in February 2024 as the Assistant Director of Development. In this role, he leverages his background in business, fundraising, and relationship management to strengthen the organization’s financial sustainability and growth.

Beyond his work at YMWAP, Elo serves as an Advisory Board Member for the Resident Services Department of the Cambridge Housing Authority, where he supports fundraising strategies for youth programming and families.

Before joining YMWAP, Elo served as Development Manager at the Mystic River Watershed Association, where he led corporate engagement and partnership development. His professional background also includes experience in sales and recruiting.

Elo earned his B.S. in Business Administration from Bryant University, where he was also a member of the football team.

Born and raised in the Boston area, Max is a graduate of the University of Rhode Island’s Harrington School of Communications and Media with a degree in Communications and Public Relations with a minor in Business. He has a passion for youth development and communication, with extensive experience in leadership and digital media. Max served as Assistant Director at Camp Hale, where he led recruitment, training, and supervision of staff, ensuring a positive and impactful camp experience for all. His work also included curriculum development, program enhancement, and community outreach to expand the camp’s reach.

Max has also worked as a Communications Assistant at MIT Sloan School of Management, where he managed administrative tasks for a communications team, coordinated social media and multimedia content, and supported major project workstreams. His role as a Communications Fellow at the Massachusetts Competitive Partnership allowed him to hone his skills in website design, social media strategy, and public relations. Max brings a strategic mindset and a collaborative approach to all his work, focusing on creativity, communication, and leadership.

Martin is a seasoned finance professional with a passion for community development. As the Director of Finance and Human Resources, he brings over 15 years of experience in financial management, leadership, and community engagement.

Born in the Dominican Republic, Martin moved to Boston at the age of two and has called it home ever since. He graduated from the University of Massachusetts, Amherst in 2009 with a degree in Economics. Martin’s finance career spans multiple industries, including commercial banking and non-profit management. In his role , he has played a key role in building financial systems, ensuring compliance, and leading human resources.

Martin is dedicated to giving back to his community. He served as a member of Codman Academy Charter Public School’s Board of Trustees for 7 years and led financial literacy seminars for high school students, empowering them with essential life skills.

With his expertise in finance and commitment to community development, Martin continues to make a positive impact in the lives of individuals and organizations.

Bruce Baptista is the Dean of Students at Boston Collegiate Charter School (BCCS). Bruce shares, “The young men at BCCS have gained a sense of camaraderie and a supportive community through their participation in YMWAP. Their involvement extends beyond casual friendships, as they actively check in with their peers to ensure they are keeping up with their schoolwork. This level of support and accountability is indicative of the strong bond they’ve developed within the program. They continue to maintain these connections through regular texting and offer assistance to one another during challenging times. YMWAP has cultivated a sense of unity and mutual support among the students, turning them into a closely-knit brotherhood.”

Mitchell is the Physical Education teacher at Ruth Batson Academy (formerly BCLA). He is the coach for the Varsity girls’ basketball program (defending city champions), the JV boys’ soccer team (undefeated 1st season) and the outdoor track and field teams. He founded and established a program in 2012 called Herc42skills. Herc42skills is a basketball skill development program that was established to provide young student athletes an opportunity to develop physically as well as fundamentally. It is a differentiated programs for boys and girls of all ages and abilities. They have worked with many college and professional athletes across New England. They aim to help provide athletes a safe learning environment for maximum success. Mitch has also organized a women’s basketball tournament called “Mitch’s women’s tournament” in Boston for the last 14 years to help empower women through sports. They use the tournament as a fundraiser for backpacks and school supplies for inner city youth. Last year they passed out 450 bags full of supplies to less fortunate underprivileged youth.

Born in Jacksonville, FL, and raised in Boston, Eleazar Clayton graduated from East Boston High School where he received a scholarship to North Platte Jr. College. He later graduated from the University of Massachusetts Dartmouth where he studied History, and Sociology. Eleazar has worked as a therapeutic mentor engaging with children with social, and emotional issues. He is currently working at New Mission High School coaching JV boys basketball, and leading Project Ochendo where he mentors students of color, helping them improve their study skills, grades, and to access and persist at college.

Lance grew up in Delray Beach, Florida, in Palm Beach County. He graduated from Assumption University in Worcester, MA, in 2011 with a B.A. in Human Services. During his time at Assumption, Lance was given the incredible opportunity to join the Miami Dolphins practice squad, thanks to his high school football coach, Keith Byars (former New England Patriots running back, 1996-97).

Lance’s career began in social work with the Department of Children and Families (DCF) in the north-central region of Massachusetts. After his time with DCF, Lance went on to oversee a foster care program in Worcester, MA, where he played a key role in helping troubled, at-risk youth find stable housing.

Passionate about making a difference in the lives of students, Lance pursued and earned his Master’s degree in School Counseling from Assumption University. His work focuses on helping students navigate life’s stressors and traumatic experiences. Lance understands that when students face such challenges, their lives can easily become unbalanced, and he is dedicated to bringing healing through compassionate support. His goal is to help students develop healthy perceptions of themselves, build stronger relationships, and ultimately know themselves as peaceful, complete, whole, and safe.

In addition to his counseling work, Lance is the running back coach and recruiter for the Framingham State University football team. He is also the co-owner of a New England-based dog food company, combining his passion for both sports and business.

Bio coming soon!

Bio coming soon!

Bio coming soon!

Bio coming soon!

Bio coming soon!

Near-peer Mentors are an integral part of YMWAP’s multi-level mentoring model. They develop leadership skills, support recruiting, assist at weekly groups, attend funder events, lead community service,  and build college and career readiness skills that include research, critical thinking, and effective communications.

Mike Long attends many YMWAP meetings and helps young men understand how policing works and teaches them about careers in criminal justice.

Giovany Morales-Ramos is currently an IT Manager and Consultant at InSource. Previously, Gio was the Director of Instructional Technology for Buckingham, Browne, and Nichols. He is a former Young Man With A Plan school based mentor for Boston Prep. He now serves as webmaster for YMWAP and is responsible for designing and maintaining the YMWAP website.

Giovany holds a Bachelor’s in Science from Wentworth Institute of Technology in Mechanical Engineering and a Master’s in Education from Harvard Graduate School of Education in School Leadership.

Shannon has worked in nonprofit fundraising and development since 2020, primarily supporting youth-serving and arts and culture organizations, including Breakthrough Greater Boston, Boys and Girls Club of Lawrence, and New Repertory Theatre.

She began her nonprofit career as a grant writer and quickly developed a passion for development operations and database management. Shannon supports the YMWAP team with database administration, grant writing, file organization, website management, and fundraising thought-partnership.

Shannon holds a B.A. in Writing Arts and a B.A. in Radio/TV/Film Production from Rowan University, where she graduated Summa Cum Laude.