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Director of Community Programs

Castle Square Tenants Organization
Job Title: Director of Community Programs
Job Type:
Job Search Ends:
May 24th, 2019
Organization's Website:


Castle Square Tenants Organization’s (CSTO) mission is to promote the economic, educational and social empowerment of low income individuals by providing access to safe, quality affordable housing and supportive direct service programs. CSTO offers programs for residents of the Castle Square affordable housing complex and members of the surrounding community that include a quality after school enrichment programming for grades K-8, innovative job readiness/youth development programs for under resourced teens, an adult technology class, wellness programming for seniors and a social enterprise that provides low cost computer equipment and IT support. CSTO also co-owns and co-manages the Castle Square complex, which includes 500 apartments and 13 commercial spaces in Boston’s South End.


Position Summary


A key member of the Leadership Team and reporting to the Executive Director, the Director of Community Programs oversees all aspects of CSTO’s direct service youth programs. S/he is a proven leader, adept at rallying a team around a shared vision and building strong external relationships. Equally important, s/he must be committed to CSTO’s mission, and approach challenges and conflicts with candor, composure and humor. Position is full time and compensation is commensurate with experience.


Duties and Responsibilities


Program Leadership and Management:

  • Develop short and long term plans to ensure ongoing programmatic excellence
  • Vet and research new program initiatives
  • Work closely with the Executive Director and Chief Financial Officer to set and meet department budget
  • Establish goals, systems and tools for tracking outcomes and measurements
  • Support staff in preparing outcome reports and reviewing results  
  • Refine systems, processes and tools for the collection, and sharing of knowledge that is generated by the programs
  • Oversee curriculum development
  • Supervise participant recruitment strategy, including establishing new pipelines and partnerships
  • Work with CSTO staff to develop communications plan for programs
  • Assist leadership in re-establishing Program Advisory Committee
  • Work closely with Winn Management staff as lead contact for youth programs and program related facilities operation


Staff Management and Development:

  • Support program managers in planning and implement programming
  • Supervise all program staff either directly or through intermediary supervisors
  • Attract, develop, coach and retain high-performing team members
  • Create professional development and performance evaluation plans for program staff
  • Help program staff produce and adhere to work plans
  • Provide leadership for building inter-team communication and cohesiveness


Other Responsibilities:

  • Develop and maintain relationships with corporate and community partners including post secondary institutions, elementary and secondary schools and nonprofits
  • Collaborate with the Executive Director, development staff and program managers on grant applications and new funding initiatives
  • Serve on senior leadership team and work collaboratively to integrate cross program activities and functions and develop and implement organization wide policies and procedures
  • Coordinate program contribution to bimonthly newsletter
  • Manage program staff’s contribution to CSTO organization-wide events
  • Ensures compliance with state licensure requirements for EEC and voucher program for K-8 after-school program




The ideal candidate demonstrates the following qualifications:


  • Commitment to CSTO’s mission
  • At least two years of experience leading an outcomes-based program
  • Success developing and evaluating program models, particularly youth programs, and working with diverse populations
  • Experience in developing and managing outward facing partnerships
  • Demonstrated ability to guide, manage and motivate staff
  • Ability to recognize and nurture talent
  • Track record of developing program evaluations.
  • Understanding of how to allocate organizational resources efficiently and for maximum impact
  • Strong belief in the power of community and a collaborative approach to problem solving
  • Sense of humor
  • Excellent presentation, oral and written communication skills.
  • Proficient in basic Microsoft Suite programs; database experience preferred
  • Bachelor’s Degree, Master’s preferred (or equivalent experience)
  • Proficient in Chinese and/or Spanish languages (preferred not required)
  • CORI and SORI required


Applications will be accepted until the position is filled.


Interested candidates should email a cover letter and resume to hiring@cstoboston.org


133 Federal Street, Suite 802 | Boston, MA 02110
Phone: 617.426.2606
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