Type:  Consultant (6 Months) with path to Full-Time Position

Location: Moon Township, PA (hybrid-remote — field, office, and community-based)

Reports To: Executive Director

Compensation: $30 per-hour (up to $5,000 a month)

Contact: Rachael Masterson, Project Manager, info@hollowoak.org

About Hollow Oak Land Trust

Hollow Oak Land Trust is a mission-driven nonprofit founded in 1991 to protect and connect greenspace across the Pittsburgh region. Hollow Oak has nine conservation areas in Allegheny and Beaver Counties as permanent wildlife refuges protecting water quality and providing public access to nature through multi-use trails.Through land acquisition, habitat stewardship, sustainable trail design, municipal partnerships, and environmental education, Hollow Oak benefits people and wildlife alike. 

Position Summary

Hollow Oak Land Trust is hiring a Trail Services Coordinator to launch its mission-driven, revenue-generating Trail Services social enterprise. Trail Services offers specialized trail design and planning to help municipalities and nonprofit partners develop and expand trail systems that minimize environmental impact while maximizing enjoyment for hikers and mountain bikers. The role centers on building a sustainable, growing pipeline for this fee-for-service trail planning, design, and implementation program. Experience in sales and entrepreneurial business development is highly desirable.

This position begins as a 6-month, full-time contract, with the opportunity to grow into a full-time, year-round role as additional revenue is secured. Hollow Oak is looking for someone with experience in business development, sales, or fundraising, along with contractor management and partnership development.

Duties & ResponsibilitiesTrail Services Business Development 

• Identify and cultivate Trail Services clients — municipal parks, land trusts, nonprofits, and land-management partners.
• Develop client proposals, pitches, and scopes of work for fee-for-service trail projects.
• Build strategic partnerships with municipalities and Allegheny Green Web coalition members
• Support HOLT stewardship staff on internal trail planning — assessing existing trail systems, designing improvements, and creating new natural-surface, multi-use trails for Hollow Oak's conservation areas.
• Use in-house CRM software to track the client pipeline from outreach through contract and delivery.
• Develop pricing, contracting, and financial tracking for the enterprise.
• Represent Hollow Oak Trail Services at municipal meetings, conferences, and partner events.
• Adapt the Trail Services business plan as client experience informs the pipeline.

Growth Path: Flexible Structure with Room to Grow

This position is a contract of up to 6 months, structured as 20 to 40 hours per week, with the opportunity to move into a full-time, year-round role as additional revenue and funding are secured. Advancement to full-time, year-round status will be evaluated based on milestones such as:

• Trail Services client contacts and contracts secured
• Prospect pipeline growth and partner relationship development
• Meeting projected revenue goals

Specific structure, milestones, and timelines will be discussed and set collaboratively with the Executive Director.

Qualifications

• 2–4 years of experience in business development, sales, and/or nonprofit fundraising.
• Comfort with cold calling, pitching, and relationship-building with partners and clients.
• Strong written and verbal communication skills, including the ability to write proposals.
• Basic financial literacy (budgeting, costing, revenue tracking) and experience with Microsoft Excel and/or Google Sheets required.
• Self-directed and comfortable in an early-stage, pilot-program environment.
• Ability to lift up to 50 lbs and walk over 3 miles on uneven, natural terrain for trail assessments and site visits.
• Some experience with natural-surface trail building or maintenance — volunteer trail experience is a plus.
• Passion for the outdoors, conservation, and community-based greenspace work.
• Familiarity with the Pittsburgh/Allegheny County business or nonprofit landscape is a plus.

Work Environment

This role is primarily relationship- and desk-based, with fieldwork and site visits, partner meetings, and attendance at community or fundraising events (including some evenings and weekends, particularly around seasonal events).

Hollow Oak Land Trust is an equal opportunity employer and encourages applicants from all backgrounds
to apply.