HISTORY & BACKGROUND
Miles of Freedom empowers individuals, families, and communities impacted by incarceration. We do this through wraparound reentry services that include job readiness, case management, and transitional employment opportunities through our Lawn Service Social Enterprise.
Our Lawn Service Program provides workforce development, paid training, structure, accountability, and immediate income to individuals working toward long-term stability and self-sufficiency. In addition to serving residential and commercial lawn care clients throughout the Dallas area, the program serves as a hands-on training environment for participants overcoming significant employment barriers.
POSITION SUMMARY
Miles of Freedom is seeking a highly motivated, dependable, and hands-on Lawn Service Supervisor to oversee daily lawn service operations, supervise crews, maintain quality standards, and support workforce development efforts within the organization’s transitional employment program.
This position is responsible for supervising lawn crews, ensuring equipment accountability and maintenance, monitoring contract quality, training participants, and maintaining safe and professional job site operations. The Lawn Service Supervisor is expected to lead by example while balancing operational efficiency with leadership and participant development. This is a working supervisor role requiring both field leadership and active participation in lawn care services.
PRIMARY RESPONSIBILITIES
CREW LEADERSHIP & SUPERVISION
• Supervise and lead lawn service crews on residential and commercial properties
• Build a culture of accountability, teamwork, professionalism, and respect
• Provide hands-on guidance, coaching, and support to participants and crew members
• Ensure crews remain productive and on task throughout the workday
• Address performance concerns promptly and professionally
• Assist with implementing corrective action plans when necessary
• Support participant growth through strengths-based feedback and skill development
OPERATIONS & SCHEDULING
• Ensure timely completion of all assigned contracts and services
• Monitor productivity, route efficiency, and crew performance
• Maintain communication with leadership regarding operational concerns, delays, or
staffing needs
• Assist in tracking attendance and job completion
LAWN CARE & FIELD OPERATIONS
• Participate in all aspects of lawn maintenance, including mowing, edging, trimming,
weed eating, blowing, cleanup, and other landscaping tasks
• Operate commercial lawn equipment safely and effectively
• Safely drive company vehicles and transport crews and equipment using utility trailers
• Load, secure, and unload equipment appropriately
EQUIPMENT & QUALITY CONTROL
• Conduct routine inspections and maintenance checks on vehicles, trailers, and lawn
equipment
• Report maintenance concerns immediately and help prevent avoidable damage
• Ensure equipment is operated properly and stored securely
• Maintain high standards for property appearance and contract completion
• Perform quality control inspections on completed properties
SAFETY & COMPLIANCE
• Ensure all staff and participants follow safety procedures and organizational policies
• Conduct routine safety checks and address hazards immediately
• Promote safe equipment operation and proper use of PPE
• Maintain incident documentation and report concerns to leadership
DOCUMENTATION & COMMUNICATION
• Maintain accurate logs, records, and reporting related to crew operations
• Utilize basic technology for communication, scheduling, documentation, and photo
sharing
• Communicate professionally with clients, staff, vendors, and participants
• Assist with customer service concerns or on-site client communication when necessary
QUALIFICATIONS
• Valid and unrestricted Texas Driver’s License in good standing required
• Experience pulling and maneuvering a 15’ or larger utility trailer required
• Prior lawn care, landscaping, or grounds maintenance experience required
• Prior supervisory, team lead, or project management experience strongly preferred
• Ability to lead crews while maintaining professionalism and accountability
• Strong organizational, communication, and leadership skills
• Ability to work independently and make sound decisions in the field
• Basic computer and smartphone skills required
• Ability to maintain confidentiality and professionalism at all times
• Commitment to supporting individuals impacted by incarceration and employment
barriers
ADDITIONAL MILES OF FREEDOM EXPECTATIONS
• Demonstrates alignment with the mission and values of Miles of Freedom
• Utilizes strengths-based approaches when working with participants
• Leads with professionalism, patience, and accountability
• Maintains ethical standards and confidentiality
• Represents the organization positively within the community
PHYSICAL DEMANDS & WORK ENVIRONMENT
• Ability to lift and carry up to 50 pounds regularly
• Ability to work outdoors in varying weather conditions
• Frequent standing, walking, bending, lifting, and equipment operation required
• Ability to safely navigate residential and commercial job sites
POSITION DETAILS
TO APPLY
Please submit a current resume and brief cover letter to:
Tahvia Merrill
Contact@MilesofFreedom.org
MILES of Freedom is committed to providing a hands-on experience for undergraduate and graduate students studying Communications, Nonprofit Management, Public Health, Nutrition, Social Work, or other Human Services studies.
Location: Dallas, TX (On-site with some flexibility)
Position Type: Internship (Unpaid, with potential for academic credit)
Hours: Flexible, 10-20 hours per week
The Food Pantry Intern will support the operations and growth of MOF’s MLK Food Pantry which plays a crucial role in improving food access for communities impacted by incarceration and poverty. This internship is designed to give students hands-on experience in public health practice, while addressing key social determinants of health, including food insecurity, economic stability, and community wellness.
Please send your resume and a brief statement of interest to Contact@Milesoffreedom.org
Applications are accepted on a rolling basis.
Location: Dallas, TX
Position Type: Internship (Unpaid, with potential for academic credit)
Hours: Minimum 3 days a week during normal business hours
The Social Work Intern will play an essential role in supporting MOF’s mission by assisting with direct services, resource coordination, and program support for individuals returning home from incarceration. This hands-on opportunity is ideal for students seeking real-world experience in community-based social work, reentry services, and nonprofit operations.
Please send your resume and a brief statement of interest to Contact@Milesoffreedom.org
Applications are accepted on a rolling basis.
Location: Dallas, TX (Hybrid opportunities available)
Position Type: Internship (Unpaid, with potential for academic credit)
Hours: Flexible, 10-20 hours per week
The Fundraising & Marketing Intern will support MOF’s mission by assisting with donor engagement, fundraising initiatives, and communication strategies to amplify the organization’s impact. This role is perfect for students interested in nonprofit development, digital marketing, community outreach, and social justice.
Please send your resume and a brief statement of interest to Contact@Milesoffreedom.org. Applications are accepted on a rolling basis.
