Jasmine Naylor

Jasmine Naylor, MBA, MS is a dynamic leader with two decades of cross-sector executive leadership experience in business administration and operations.  As an advocate and mentor, Jasmine integrates her passion for activating the leadership abilities of others across her versatile roles.

Jasmine currently serves as the Executive Vice President and Chief Strategy Officer at Naylor Nation Real Estate and Handy Hands Management, organizations she co-founded with her husband. Together, they operate successful real estate companies including 30 long term rentals across Massachusetts & Puerto Rico.  They also fix and flip properties for profit, and recently have added new construction development to their portfolio and serve as court-appointed receivers in Hampden County. 

Jasmine is the founder of Jasmine Naylor Enterprise, an independent consulting firm providing financial education and coaching to empower people in changing their relationships with money in life, business, marriage, and ministry. Through coaching, speaking, and training, Jasmine is passionate about helping believers and communities of color overcome financial oppression and build wealth, God’s way. In 2022, Jasmine executed and hosted Springfield’s first Work to Profit Conference: Real Estate Edition, an innovative community symposium designed to teach professionals and entrepreneurs to become profitable real estate investors. Other signature programs include her popular Master Your Money Seminar, Money Accelerator and Property Profits courses.

Jasmine is the former Executive Vice President and Chief Strategy Officer of the Massachusetts League of Community Health Centers in Boston, Massachusetts, a statewide Primary Care Association representing health centers and the communities they serve across Massachusetts through policy and advocacy, technical assistance, and workforce development. In her role, Jasmine oversaw the strategic functions of the organization, including fundraising, stakeholder engagement, and business partnerships. Jasmine spearheaded the integration of the League’s Diversity, Equity,  Inclusion, and Belonging (DEIB) efforts and the launch of its first Health Equity Institute focused on eliminating disparities within the BIPOC community ensuring equitable care delivery, treatments, and outcomes are afforded to all. In her previous role as the League’s Chief of Staff, Jasmine served as the trusted advisor and partner to the League’s Chief Executive Officer, Michael Curry, Esq.

Prior to her work with the League, Jasmine served as the Chief Executive Vice President and Privacy Officer at Caring Health Center, a Federally Qualified Health Center serving over 19,000 underserved and medically vulnerable communities across western Massachusetts, where she facilitated the implementation of a multimillion-dollar, surplus-generating Medicaid Accountable Care Organization. Jasmine formerly held roles as the Finance and Administrative Director at various churches in Springfield, and started her career in corporate logistics management at Collins Aerospace in Windsor Locks, Connecticut.

Jasmine is married to her high school sweetheart of 20 years, with whom she shares five talented and down-to-earth children ages 24, 21, 14, and 2 and an infant who teaches her every day what it means to truly live wealthy. A former teen mom and Springfield native, Jasmine is a testament to the power of belief and has dedicated her life to strengthening local ministries, neighborhoods, and communities through mentorship. She has helped executives, start-ups, non-profits, and entrepreneurs across the fields of healthcare, marketing, education, government, aerospace, real estate, ministry, and human services to financially flourish.

Jasmine holds a Master of Business Administration in Entrepreneurial Thinking and Innovative Practices, a Master of Science in Nonprofit Management and Philanthropy, and a Bachelor of Science in Business Administration from Bay Path University, where she was formerly named a Presidential Scholar and Alumni of the Year.