Hiring: Assistant Farm Manager – Upswing Farm – Pepperell, MA
Assistant Farm Manager
Full Time, Year Round
Job Overview:
Step into a leadership role on a highly successful, certified organic farm with established systems, skilled farmer/owners, and a proven track record of high-quality, profitable production. This is a
year-round position offering competitive compensation, and the chance to work as a professional farmer with real autonomy and responsibility.
We’re looking for an experienced, committed farmer who thrives both working solo in the field and leading a team. You’ll oversee field operations, support crew members, and collaborate closely
with the farm owners to ensure smooth, efficient production. Our farm has robust infrastructure and mechanization, so your expertise is amplified by smart systems that help you work efficiently.
This role is perfect for someone who wants to grow with the farm long-term, with opportunities for increased responsibility, profit sharing, and meaningful impact. If you’re ready to take the next step in your farming career, we want to hear from you.
Key Responsibilities
• Manage and support a team of up to 8 crew members during peak season, as well as “work-for-share” participants, providing guidance, quality monitoring, pace-setting, feedback, and mentoring to ensure everyone contributes effectively to farm work.
• Collaborate closely with farmer/owners, observing and communicating to understand farm operations, production priorities, and team needs.
• Participate in hands-on field work, including planting, cultivation, harvesting, and tractor operation, to maintain productivity and quality standards.
• Assist with planning and organizing projects, including bed prep, planting schedules, and crop rotation.
• Flexible opportunities to support crew at distribution sites and markets, representing the farm professionally and ensuring smooth operations.
• Take initiative to anticipate farm and crew needs, identifying and addressing tasks proactively to keep operations running efficiently.
• Train and coach new crew members, influencing a culture of professionalism, collaboration, and high-quality standards.
• Help maintain and monitor farm equipment, tools, and infrastructure to ensure safety, efficiency, and longevity.
Desired Qualifications
• Experience: Minimum of 4+ seasons working on a diversified vegetable farm, with proven experience managing crews and leading field operations.
• Leadership & Professionalism: Demonstrated ability to lead, mentor, and support a team; professional, adaptable, and able to work independently as well as collaboratively with farm owners and crew.
• Technical Skills: Comfortable operating tractors, farm tools, and other equipment; solid understanding of basic diversified vegetable agronomy, including crop care, planting, and cultivation principles.
• Work Ethic & Initiative: Highly motivated, proactive, and able to anticipate farm and crew needs; capable of getting things done without being asked.
• Physical Stamina: Enjoys hands-on farm work and is prepared for the physical demands of field, greenhouse, and high tunnel operations.
• Communication & Problem-Solving: Strong interpersonal skills, able to communicate effectively and kindly with crew members, farm owners, and distribution staff; able to identify challenges and suggest solutions.
• Attention to Quality & Efficiency: Balances speed and productivity with high standards for crop quality and crew performance.
Hours & Compensation
• Year-Round Position: This is a full-time, year-round role, with approximately 2,000 hours annually. Workload varies seasonally, with more hours during the spring, summer, and fall growing seasons, and fewer hours during the winter.
• Flexible Schedule: Peak season may require up to 50 hours per week. Winter hours are reduced and flexible, allowing for work-life balance while maintaining meaningful contributions to farm operations.
• Compensation: $45,000-$55,000 annually depending on experience and skillset. The pay structure is flexible and can be discussed to suit both the farm’s budget and the candidate’s preferences.
• Benefits: Paid wellness time (80 hours annually), paid sick leave (1 hour paid sick time for every 30 hours worked), gear stipend, and access to farm-provided tools and equipment.
Optional on-farm housing available to rent.
• Professional Growth Opportunities: Compensation and autonomy reflect the candidate’s experience and commitment. There is potential for long-term growth within the farm, including the possibility of expanded responsibilities and profit-sharing over time.
How to Apply
If you are excited about year-round work on a successful, experienced, and well-equipped farm, we want to hear from you.
To apply, please submit:
• A resume detailing your farming experience and relevant skills
• A brief cover letter explaining why you’re interested in this position and what you would bring to our farm team
Applications can be sent to: brittany@upswingfarm.com with the subject line “Assistant Farm Manager Application.”
Hiring Statement
Upswing Farm is an Equal Opportunity Employer, and we work to build and maintain a culture of inclusion for all employees and potential employees.
Hiring Process
After reviewing your application, we will contact you for a 45-60 minute virtual interview. The next phase is a minimum one day, paid working interview on the farm.
We aim to have the new team member start in January or February, 2026.
About Us
Our Farm
We love growing high quality produce that goes directly to the folks who are going to eat it. High quality to us means delicious, nutritious, long lasting, and grown, harvested, and distributed in a
way that allows the farm, the farmers, and the soils to keep producing food for years to come.
Upswing Farm got its start on leased land in Ashland/Holliston MA in 2016. After losing our lease in 2019, we farmed piecemeal on several small plots in 2020 while we worked to secure our current
location, a 131 acre APR farm in Pepperell, MA. We still distribute twice/week to our original customer base though a 230 member CSA and a weekly summer farmers market. We have a 270
member on site CSA and we are open for retail sales during distribution. We do a small amount of wholesaling, but CSA is the core of what we do. We offer a lot of choice and flexibility, which we have nuanced over the years, leading to high retention rates and increased total membership each year.
We are certified organic and “real organic” and our greatest pride is in our soils which we have worked diligently to improve since arriving here in 2021. Through mineral amendments, composting, cover cropping and using reduced tillage methods we have seen impressive results and our yields and crop quality have increased each season. 2024 and 2025 were exceptional growing seasons for our farm. We now cultivate 19 acres of produce and cut flowers, leaving at least 6 acres fallow each season. We have 6 high tunnels used for year-round production and two propagation greenhouses.
We are building an on-farm composting system to localize our fertility inputs.
This year we planted an acre of blueberries, ½ acre of raspberries and an acre of asparagus. We also rent a 2-acre asparagus field.
We are excited to be adding new events and workshops, working towards our goal of being an open and welcoming community space.
We are also very interested in adding a grazing/animal component to our farm systems.
Our Team
The foundation of our team is a close-knit group; many have been with us for four or five seasons.
The owners, Kevin and Brittany, work full time on farm, and are very involved in daily operations. We have built solid working relationships and a culture of commitment to quality and efficiency as a team, with respect for individual well-being. We are supported by several year-round, full and part-time crew members, ten work-for-share members and a seasonal summer crew of 3-5 additional
folks. We look forward to team lunches, birthday desserts and the moments of awe, wonder and deep satisfaction that come from working on a farm. We love the work that we do and the time we
spend together making this farm possible.
Our Location
Close to the heart of New England, we are just 45 minutes from the Ocean, the Mountains and both Boston and Worcester. Our farm is 131 acres, abutted by open space and the Nissitissit River.
There are places in town to swim and hike, a bike path that connects to other area towns, and a small grocery, pharmacy and other amenities.
