Summary:
The Trail Keepers Lead Field Supervisor is a seasonal employee of the Sidewalk Detroit team, responsible for leading and supporting Trail Keepers participants in day-to-day field operations. This role centers youth workforce development and hands-on environmental stewardship, with a strong focus on curriculum implementation, park maintenance, and conservation practices.

The Lead Field Supervisor works closely with Sidewalk staff and program partners to guide participants through a range of outdoor projects, including tree planting and care, trail maintenance, invasive species management, environmental monitoring, and data collection. This position plays a critical role in maintaining a safe, organized, and educational field environment while modeling leadership, teamwork, and care for public land.

Duties:

• Program & Team Leadership
• Provide day-to-day supervision of Trail Keepers participants, including communication, attendance tracking, and task coordination
• Foster a supportive, inclusive, and youth-centered learning environment
• Serve as a mentor and role model, reinforcing professional skills, teamwork, and accountability

• Curriculum & Workforce Development
• Assist with the development and delivery of environmental and workforce development curriculum
• Support certification programs, workshops, and educational field trips
• Help translate fieldwork into learning outcomes related to conservation, stewardship, and career pathways

• Field Operations & Project Execution
• Lead and support hands-on field activities such as trail maintenance, tree planting and care, invasive species management, and habitat restoration
• Collaborate with Sidewalk Detroit staff and partners to execute work plans and project goals
• Ensure tools, materials, and equipment are used safely and responsibly

• Monitoring, Data & Reporting
• Support data collection, environmental monitoring, and basic field reporting
• Communicate progress, challenges, and observations to program staff

• Safety & Site Stewardship
• Maintain a strong focus on field safety, risk awareness, and best practices
• Uphold care for public spaces and promote environmental responsibility

Organizational Culture 

• Commit to regular project status meetings or check-ins with Sidewalk Detroit staff
• Participate in company think-tanks/strategy sessions as needed

Qualifications 

• Experience supervising youth or crews in outdoor, environmental, or community-based settings
• Background in park maintenance, conservation, forestry, landscaping, or environmental education
• Strong communication and organizational skills
  Comfort working outdoors in varying weather conditions
• First Aid/CPR certification (or willingness to obtain)
• Knowledge of Detroit neighborhoods and communities
• Knowledge of Eliza Howell Park ( preferred but not required)
• Excellent oral and written communication skills
• Proficiency in Microsoft Office, including Excel, Word, Powerpoint etc

Program Timeline 

Daily Schedule: 

• Monday to Thursday
• 6 hours day
• 9am-3pm (Lunch not provided)

Weekly Schedule 

• Mondays: Mapping Mondays
• Tuesdays: Teaching Tuesdays
• Wednesdays: Working Wednesdays 
• Thursdays: Field Trips, Lunch and learns

 Monthly Schedule 

• May: Tree care 101
• June: Urban Forestry
• July: Environmental education & Summer Camp
• August: End of season & Final presentations