Railroad Street

RSYP is Hiring!

March 14, 2022

Railroad Street Youth Project
Development Associate – Position Announcement
March 2022


Title: Development Associate
Location: Great Barrington, MA (the Beautiful Berkshires)
Position: Part-time/ Full-time, associate
Compensation: $45,000-50,000
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 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 position – The Development Associate is responsible for:

  • Supporting the Development Director to raise an annual budget of approximately $1,000,000 through events, donor cultivation, major gifts and annual appeal.
  • Curating the donor database and managing gift processing, acknowledgements, communication recording, and ensuring real time data accuracy.
  • Coordinating and implementing fundraising mailings, donor communications, dissemination of marketing materials and scheduled social media posts.
  • Participating in cultivation planning, activities and fundraising event planning, implementation and follow-up.

Core qualifications -- The Development Associate embodies RSYP’s mission in day-to-day interactions with young people and approach to teamwork and problem solving. This position requires a person to have the following core competencies:

  • Experience in the field of development, or translatable field, and excitement to share and grow it. 
  • Expertise with database software (donor database software preferred), as well as Microsoft office suite and Google calendar. Adobe Creative Suite a plus. Proficient with social media.
  • Enjoyment, curiosity and ease connecting with people and exploring shared interests and passions. Excellent verbal and written communication skills
  • Strong skill sets in social justice and cultural competency literacies and experience in working with others across social differences including age, race, socio-economic status, gender, sexuality, and ability.


To Apply – Please send a resume and cover letter to Tiffany Riva, Director of Development, tiffany@rsyp.org. Priority deadline, April 15, 2022.


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.