Trail Keepers Lead Field Supervisor - Seasonal Employee

Start Date: April 6 - August 21

28 hours per week

Pay $25/hr based on qualifications

Benefits: 12 hours of paid holiday, 16 hours of earned sick days

APPLY HERE or Scan QR code (Applications close March 12th, 2026)

About:

Sidewalk Detroit is dedicated to improving livability in metro-Detroit neighborhoods and public spaces through the lens of creativity, arts, culture, and collaborative design. We are passionate about the power of engagement with residents and artists to create effective, long-lasting, and sustainable plans for public space. We complete this work through deep engagement with residents and artists, place-based event production, and public art planning.

Trail Keepers is a youth workforce development program for ages 14-24 to contribute to park improvement projects while earning certifications, developing leadership skills, and exploring pathways in conservation, urban forestry, and land stewardship.

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 & Workshops 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