Trail Crew Leader

Sitka Trail Works is seeking a Trail Crew Lead to manage our trail maintenance program and lead our paid summer crew in Sitka, Alaska. The ideal candidate is a detail-oriented professional with strong technical skills for building trails in the rainforest and a leader with experience motivating crews in challenging environments. Pay: $26-36/hour, depending on experience. Start-End Date: April 26, 2027 - September 30, 2027

About Sitka Trail Works

We’re a small nonprofit with an outsized impact, uplifting the health of our community by building, maintaining and promoting trails. Since 1997, Sitka Trail Works has leveraged millions in federal and state funds to facilitate dozens of major trail enhancement projects, developing one of the most robust trail systems in the state. We have recently started another remote crew working on projects in other parts of Southeast Alaska. The growth of volunteer and youth programs in recent years has been led by a dynamic team of five year-round staff and seven seasonal employees, with support from an active nine-member volunteer Board of Directors.

About the season

This summer, the crew will focus on high priority maintenance needs across municipal, State Parks, and Tongass National Forest trails on the road system, including Mosquito Cove, aasda Héen (Indian River), Gavan Hill, and elsewhere. The crew will also deploy on multi-day trips to boat-access trails like Mount Edgecumbe, Lake Eva, Sealion Cove, and Salmon Lake. In addition to the Crew Lead, we will hire three full-time crew members. The Sitka Crew will occasionally work alongside the Remote Crew, another four person trail crew, on projects and training. The paid crew’s work is supported by the efforts of a large volunteer base, with over a hundred volunteers investing over 1,200 volunteer hours in 2026.

Position overview

Compensation

$26-36/hour, Dependent on Experience (DOE)

Pre-Season (April 26 - May 10): Flexible, part-time schedule for scoping, tool preparation, recruitment, training, and volunteer events. Start date negotiable.

Schedule

Summer (May 10 - September 16): Supervising full crew. Four-day work week, 10-hour days. Some weekends and overnight trips required.

Post-Season (September 16 - September 30): Flexible, part-time schedule for tool inventory and maintenance, reporting, and volunteer events. End date negotiable.

Responsibilities and duties

The Crew Lead will:

• Lead people
• Motivate and supervise crew members in completing projects safely and efficiently
• Foster a positive and productive work environment, promoting teamwork and open communication
• Participate in and lead training to share techniques with crew and volunteers
• Coordinate and teach novice and skilled volunteers during weekend events
• Represent the crew and the organization professionally when interacting with the public and partner agencies
• Lead trail work
• Assess trail conditions, scope projects, and coordinate logistics to implement maintenance
• Design and build complex trail structures (e.g. stone steps, retaining walls, small bridges)
• Maintain STW shop and tools, ensuring inventory is prepared for crew and volunteer work
• Prepare and submit reports, including timesheets, project updates, and safety logs

Minimum job requirements

• At least three seasons of experience as a trail crew member, or one season as a crew lead (or equivalent)
• USDA A-Sawyer certification for chainsaw (or equivalent, can be expired)
• Wilderness First Aid (WFA) certification (or equivalent, can be expired)

Desired qualifications

• You are a go-getter, taking responsibility for your work and lending a hand in the efforts of a small dynamic team
• You have at least three years of experience in trail maintenance and construction, preferably in very wet or rainforest environments
• You are detail oriented with high standards for your teams finished projects
• You are highly competent with a chainsaw (USFS certification can be provided on-the-job)
• You have supervised an outdoor crew for at least one season
• You respect other cultures and have an openness to learning Indigenous traditions
• You are flexible, patient, and willing to foster open and healthy communication
• You are willing to take initiative to resolve conflict, make decisions, and be a leader

Reports to: Ben Hughey, Executive Director

To apply: Apply through monday.com using this link: https://wkf.ms/4hNxDCd

Reach out to [email protected] if you have any questions about the application process.

Application Review: Applications will be reviewed on a rolling basis. Priority consideration will be given to applications received by November 30, 2026**.**

Pay: $26.00 - $36.00 per hour

Work Location: In person