Chief Executive Officer

A Maryland attorney with more than 35 years of legal experience, Jennifer is a graduate of the University of Baltimore School of Law and has deep working relationships across the state’s criminal justice system. She brings prior experience as Executive Director of a Maryland home detention business, along with a career in public service with the Office of the Public Defender, where she served as a supervisor and felony trial attorney.

Jennifer received a Governor’s Citation for dedicated service to the citizens of Maryland and is the only public service attorney to ever receive the J. Earle Plumhoff Award for Professionalism from the Baltimore County Bar Association.

She is an active member of the Maryland State Bar Association , and the bar associations in Baltimore City, Baltimore County, Harford County, Montgomery County, and Prince George’s County, the Women’s Bar Association of Maryland and the Maryland Criminal Defense Attorneys’ Association.

Jennifer’s experience, credibility, and relationships across Maryland’s legal and criminal justice partners are the foundation Sentry is built on.

Owner

A Monkton native from a family of Baltimore County firefighters, Drayton brings deep Maryland roots and years of professional experience in home detention services. His background includes several years in the business development division of Sagamore Farms, as well as leadership roles as managing partner of multiple Maryland companies. Today, he leads Sentry’s mission to help Maryland citizens remain at home, continue working, and support their families while under reliable supervision.

Accounting Manager and Program Supervisor

Melanie holds a BA in Business Administration and Management from UMBC and brings 25 years of customer service experience, including significant time at a private home detention company. Her background also includes 15 years in account management and 10 years as a pharmacy technician. She leads the team with a focus on accountability, compliance, and operational excellence, making sure every client receives professional, compassionate, and reliable support.

Client Oversight Specialist

Shana served as a Database Specialist for the Office of the Public Defender for over 30 years, supporting attorneys and maintaining critical record retention protocols. She brings prior home detention program experience to the team along with a hard-working track record across both public service and private customer service roles.

Client Management Specialist

An honors graduate of Kenwood High School's magnet program, Savanna brings years of prior home detention experience to her role. She provides professional support to clients, attorneys, and the courts, and is usually the first person you connect with when contacting Sentry.