Lead Steward

Who We Are:

Founded in 1891 by a group of visionary volunteers, The Trustees of Reservations (The Trustees) is Massachusetts’ premier conservation and preservation organization. The Trustees preserves, for public use and enjoyment, properties of exceptional scenic, historic, and ecological value in Massachusetts. Our properties are open to all, and we thrive by involving as many people as possible in all that we do. We aim to protect special places for future generations to enjoy in perpetuity and have helped protect more than 50,000 acres, including 27,000+ acres on more than 120 reservations that are open to the public. As a non-profit conservation organization, we are funded and supported entirely by our visitors, supporters, volunteers, and our 100,000 Member households. We encourage you to learn more about The Trustees on our website, .

Posting Information:

Hourly Rate:  $29.44 - $37.68

New hires are placed in the range between $30.28 - $33.65 to allow for an equitable starting salary process and continual salary growth during an employee's time at The Trustees.

Hours per week:  40 

Job Classification: Full-Time, Nonexempt 

Job Location Type:  Onsite 

Location:  Based in Windsor, MA and Stockbridge, MA offices, with stewardship responsibilities focused on Notchview and our northern Berkshire properties. 

What You’ll Do:

Your Impact: 

• Collaborate on the implementation of seasonal maintenance programs, including trail grooming and maintenance for Nordic skiing, groundskeeping, landscaping, mowing; tree and shrub care; and invasive species management including herbicide application. 

• Coordinate team management initiatives, ensuring stewardship staff, seasonal employees, and volunteers are effectively trained, motivated, and supported in their roles. 

• Facilitate open communication and foster a collaborative work environment to maximize team performance and morale. 

• Assist in the management of programming and engagement operations, including an understanding and ability to manage the ski rental program and season pass administration when necessary. 

• Support the organization and mobilization of the volunteer rescue team for enhanced visitor safety and emergency response. 

• Welcome and engage the public, providing information, assistance, and a friendly atmosphere that highlights our property’s offerings and the mission of The Trustees. 

• Perform building maintenance and custodial cleaning, both interior and exterior, including light carpentry, plumbing/drainage, electrical, painting, and masonry work as needed. 

• Operate and maintain equipment such as tractors, groomers, snowplows, ATVs, and other vehicles essential for year-round property operations. 

• Supervise and support stewardship staff, seasonal employees, and volunteers, providing training, guidance, and leadership for projects and daily operations. 

• Coordinate with specialist teams (trails, buildings & structures, and ecology) as needed to advance stewardship and conservation initiatives at Notchview. 

• Ensure exceptional visitor experience and safety by maintaining clear wayfinding signage, clean and functional facilities, and regular safety inspections and risk management protocols. 

• Assist with budget and workplan development, oversee special projects, and foster volunteer engagement opportunities in partnership with the Stewardship Manager. 

• Support special events, recreation programs, and public engagement activities that highlight our region’s offerings and the mission of The Trustees. 

• Serve as a representative of The Trustees to visitors, donors, community members, local officials, partners, and Trustees staff across departments. 

• Work weekends and evenings as required for events, snow removal, and to ensure the protection of the site and visitor safety, especially during peak ski season and inclement weather. 

• Assist and support the larger region of the Western Hills and Berkshires Region as a key part of our regional stewardship staff. 

• Perform other duties as assigned with or without accommodation. 

This is a full-time, nonexempt position working 40 hours per week, reporting directly to the Regional Stewardship Manager.

Requirements

What You’ll Need:

Skills and Experience: 

• Associates degree preferred in Natural Resources, Forestry, Park Management, Outdoor Recreation, or related field. 

• 6 – 8 years of relevant experience required. Background in facilities management and building systems is preferred. 

• Minimum of 1 year of relevant experience in land stewardship, facility maintenance, outdoor recreation management, or similar responsibilities. 

• Demonstrated leadership and “people skills” to lead, inspire, motivate, and work cooperatively with staff, volunteers, committees, Trustees members, and the visiting public. 

• Ability to maintain a positive attitude and sense of humor, especially during busy seasons and challenging weather conditions. 

• Experience with trail management, carpentry, painting, and maintenance of landscapes, structures, and building systems. 

• Ability to work both independently and collaboratively as part of a team. 

• Strong organizational skills with proven ability to manage multiple tasks, meet deadlines, and complete assigned projects efficiently. 

• Familiarity with the operation and repair of trail grooming equipment and snow machines is highly desirable. 

• The ability to operate motor vehicles, tractor/backhoe, and turf equipment. 

• Experience using a chainsaw, string trimmer, mower, blower and other small power tools. 

• Demonstrated problem solving skills: mechanical, logistical, and otherwise. 

• Have an eye for detail and concern for aesthetic quality in all aspects of landscape and facility management. 

• Be able to repair and maintain hand tools and power equipment. 

• Basic computer skills using MS Outlook, Excel, and Word and comfort using phone-based apps. 

• Strong commitment to the mission of The Trustees. 

• Be able to handle the physical demands of the job, including lifting of 75 lbs. and working in various outdoor environments and weather conditions.

• Valid driver’s license and MA DOT Medical Card, or acquire one within one month of hire, required for driving Trustees vehicles. 

• Possess a valid Massachusetts Commercial Applicator License for herbicide use or be willing and able to acquire one within three months of hire. 

• Possess a Massachusetts Hoisting License or be able to acquire one with three months of hire. 

• Flexibility to work nights and weekends as needed. 

Eligibility Criteria: 

• Current authorization to work in the United States – a candidate must have such authorization by his or her first day of employment. 

• A valid driver’s license, as well as a satisfactory driving record as outlined in The Trustees’ driving policy.

• A satisfactory criminal background (CORI) check. 

Don’t quite have all the skills and experience listed above? We still want to hear from you! Research shows that historically marginalized groups are less likely to apply if they do not meet every single requirement. We are committed to building a diverse team and encourage you to apply even if you are missing some of the skills and experience above.

Questions? Contact our People team at [email protected]

Benefits

Your Benefits:

• Sick time: 15 days per year 

• Vacation time: 20 days per year (prorated) 

• 12 observed holidays, 3 floating 

• Health insurance: You are eligible to participate in the Trustees health insurance benefit via Blue Cross Blue Shield (BCBS). BCBS also offers additional benefits, such as fitness reimbursement and rewards for healthy habits.  

• Short-Term and Long-Term Disability Insurance 

• Massachusetts Paid Family Medical Leave 

• Life Insurance  

• 401k with 5% match after 1 year of employment 

• Employee Assistance Program: Free access to a confidential service that helps employees and their communities with personal and work-related issues, such as mental health support, counseling, and financial advice.  

• Reciprocity: Enjoy access to free and discounted admission and membership to more than 50 nearby museums and cultural institutions for Trustees Staff, Volunteers and Interns. 

• Discounts: Enjoy free entry to all Trustees properties, discount event tickets, and discounted merchandise at our stores and on stays at our inns.  

• Day of Wonder: Spend one workday per year to exploring a Trustees property 

• Day of Service: Spend one workday per year to helping with a project at a Trustees property  

Equal Opportunity and Diversity: 

The Trustees is a proud equal opportunity employer and does not discriminate against any protected status including, but not limited to, age, race, ethnicity, sex, gender, sexual preferences, nation of origin, religion, or disability status and strongly encourages applications from people of color, persons with varying abilities, women, and LGBTQ+ applicants. We aspire to reflect and effectively serve the residents and communities of Massachusetts, who are at the core of our mission.    

The Trustees’ commitment to advancing the organization’s vision for this work may be found here:  Diversity, Belonging, Inclusion and Equity .