Railroad Street

Employment Opportunities


About the Position

As a member of RSYP’s 5-person Leadership Team, the Development Director (DD) will serve as a strategic organization-wide leader. This role is crucial to ensuring RSYP’s sustainable growth and requires focus on both near-term and long-term objectives.

The DD will design and execute a comprehensive fundraising strategy, as well as support the Executive Director (to whom they will report) in the development and implementation of strategic fundraising goals and activities to advance the organization’s powerful mission. They will lead fundraising efforts, manage major gifts and donor relations, plan and oversee key events, provide grants oversight, co-lead communications efforts to shape consistent, mission-centric messaging and build awareness, and foster a collaborative and inclusive work environment.

The DD will supervise a Development Associate in day-to-day activities, work closely with a contracted grant writer to maximize institutional giving opportunities, and collaborate with the Development Committee and Board to identify, cultivate, solicit, and steward prospects and donors.

Key Responsibilities


  • Create and manage a comprehensive fundraising strategy, including an annual development plan and calendar.
  • Collaborate closely with Executive Director and Leadership Team to ensure consistent messaging and the prioritization of fundraising.
  • Provide support and coordination to Development Committee and Board of Directors as a whole.

Major Gifts and Donor Relations

  • Cultivate, solicit, and steward relationships with major donors and business partners, ensuring sustained and increased support.
  • Drive an annual appeal strategy that includes two mailings.
  • Oversee new-prospect identification and prospect research, including leveraging Board networks.
  • Develop a renewed Major Donor Program in preparation for the 25th

Event Management

  • Oversee planning and execution of fundraising events, including the Annual Culinary Arts dinner.
  • Manage Event Committee, identify and solicit sponsors, and oversee marketing and ticket sales.
  • Explore opportunities around 4-8 Board-hosted small cultivation events.

Grant Oversight

  • Provide leadership and oversight for grant writing program including research, narrative strategy, and editing.


  • Shape mission-centered messaging across all platforms in partnership with the Leadership Team to effectively inspire donors and strengthen brand awareness throughout the community.
  • Create concepts and manage design process and distribution of annual report and e-newsletters.

Team Collaboration

  • Supervise, mentor, and support the Development Associate.
  • Support a contracted grant writer with strategy and to review of applications, deadlines, and opportunities.
  • Foster a collaborative and inclusive work environment, embodying RSYP’s values in all activities and fundraising efforts.

Key Qualifications

  • Genuine interest in RSYP’s mission and ability to articulate a compelling case for support.
  • 5+ years of non-profit fundraising experience, including familiarity with raising annual funds, major gifts, and event fundraising.
  • Successful track record of securing 5-figure+ giving.
  • Cultural competency skills and experience working across social differences including, age, race, socio-economic, gender, sexuality, and ability.
  • Excellent interpersonal communication and writing skills. Comfort interacting with board members, donors, staff, and constituents.
  • Ability to utilize an empowerment-based approach in messaging and development work.
  • Experience with donor database software, as well as Microsoft office suite and Google calendar. Adobe Creative Suite a plus.
  • Comfort/experience utilizing social media across platforms, including Facebook and Instagram.
  • Leadership and management experience preferred, with a strong preference for those demonstrating a facilitative approach working with a team.

RSYP is an equal opportunity employer. People who identify as working class, people of color, women, genderqueer, gay, lesbian, bisexual, transgender, queer and differently abled are strongly encouraged to apply.

Compensation: The salary range for this position is $80,000 – $95,000 annually, commensurate with skills and experience. Benefits include health insurance, paid vacation time, holidays and sick time, housing/relocation support, and RSYP’s Berkshire experience benefits package.

To express interest, please submit your cover letter and resume in confidence here. Successful candidates will highlight the following criteria in their materials: passion for RSYP’s unique mission, 5-figure giving experience, and cultural competency skills.



About the Position

Title: South Berkshire Community Health Coalition (SBCHC) Program Coordinator, Part Time

Location: Great Barrington, MA (The Beautiful Berkshires)

Position: Part-time, coordinator 24 hrs/week

Compensation: $20.00/hour

Special Benefits: Berkshire Passport ($500 annually for cultural wellness, outdoor or fitness activities), ($2,400 housing benefit (one time)

Railroad Street Youth Project (RSYP) is a small, youth-founded youth organization dedicated to youth empowerment, in the southern part of the beautiful Berkshires of western Massachusetts. AT RAILROAD STREET, YOUTH TAKE THE LEAD. They explore their full potential and become equipped to meet the challenging transition to adulthood. RSYP’s professional staff expertly pairs youth-generated ideas with community resources, empowering youth to create and oversee a wide range of innovative, life-changing projects. Unmatched in mission and scope, RSYP excels in helping youth find their voice and realize the benefits of their commitment to themselves and their community.

The SBCHC Part Time Program Coordinator supports RSYP’s Health Coalition, which aims to improve the holistic health of South County youth and families by promoting community partnership and resources. The SBCHC engages youth, parents, and community members in creating a support system/community in Southern Berkshire County that centers and enhances young people's holistic wellbeing by changing the environmental factors that put young people's wellness at risk while raising their sense of protection using data-driven, public health initiatives. We strive to make mental health and youth substance use prevention resources and tools accessible. To ensure we continue to thrive for generations to come, we invest in our young people, families, and those who guide them because youth have the power to create profound change.

The SBCHC Part-time Program Coordinator is a part-time position.  This position reports directly to the SBCHC Director and Collaborates with the Senior SBCHC Program Coordinator

The position – The SBCHC Program Part Time Coordinator is responsible for:

  • Manage Coalition email list, data coordination.
  • Support in mentorship and supervision of Coalition Community co-chairs
  • Keep the SBCHC landing page and all aspects of the RSYP website related to the SBCHC up to date, technical support for hybrid meetings, and coordination of social media content creation 
  • Program support for our Peer Health Education and Restorative Prevention Fellowship Initiatives
  • Program outreach, including social media
  • PNAS data assessment and analysis support and outreach

Core Qualifications – The SBCHC Part Time Program Coordinator embodies RSYP’s mission in day-to-day interactions with young people and approach to leadership, planning and program development, implementation, and problem-solving. This position requires a person who is:

  • Highly organized with a demonstrated capacity to multi-task projects
  • Evidenced passion for community health and asset/empowerment-based youth development and ability to share it with others.
  • Strong verbal and written communication skills with demonstrated ability to both write clearly and speak publicly
  • Excited for and adept in community/peer organizing, event or production planning, recruitment and outreach.
  • Able to work occasional nights and weekends.

To Apply – Please send a resume and cover letter to Laura Rodriguez, SBCHC Director, Laura@rsyp.org

RSYP is an equal opportunity employer. People who identify as working class, people of color, multiracial, women, genderqueer, gay, lesbian, bisexual, transgender, queer and differently-abled are strongly encouraged to apply.