Job Bank (1 current listing)

Director, Employment and Workforce Planning Organization, Pine Street Inn

Pine Street Inn opened its doors in 1969, and over nearly five decades it has grown into New England’s largest nonprofit resource for homeless and formerly homeless adults. Throughout the ‘80s and ‘90s, Pine Street expanded from offering basic necessities to offering programs that help guests take significant steps in their journey out of homelessness and regain some of what they have lost, such as relationships, life skills, employment, and housing. In the past five years, Pine Street has significantly expanded its inventory of permanent supportive housing to provide lasting solutions to homelessness. Pine Street partners with homeless individuals to help them move from the streets and shelters to a home, and assists formerly homeless individuals in retaining housing. They provide street outreach, emergency services, supportive housing, job training, and connections to employment.

They tirelessly advocate for collaborative solutions to homelessness through innovative programs that include:

Permanent Supportive Housing – More than 900 formerly homeless individuals live in 40 residences and in scattered-site rental units throughout Greater Boston. The program for tenants is a supportive housing model, coupling permanent housing with on-site support staff to help each individual regain his or her highest level of independence. Specialized housing is available for seniors, adults with mental health disabilities, and veterans. They currently have a one-year-or-longer housing retention rate of 92%.

Emergency Shelter – Each night, more than 670 men and women are provided with emergency shelter at one of Pine Street’s four locations. The Inn offers a warm and safe bed, two nutritious meals, shower and locker facilities, and health care and case management services, including substance abuse treatment and psychiatric support. Inventive programs such as Front-Door Triage and Rapid Rehousing are creating new paths out of shelters and into the stability of housing.

Job Training – Pine Street provides job training in food services and housekeeping, providing individuals with the skills they need to secure jobs. Approximately 140 individuals are served in job training programs each year. iCater is a social enterprise that extends the training and opportunities for Food Service trainees, with net proceeds directed to the job training programs.

Street Outreach – Pine Street’s outreach teams travel throughout Greater Boston to offer food, blankets, health care, and referrals to approximately 115 unsheltered men and women daily. The Inn is currently the only organization offering outreach in Boston every night. Today, Pine Street Inn serves over 1,900 individuals each day. From emergency services, to needs assessment, counseling, and case management, to job training and placement in permanent housing, Pine Street Inn is providing the short-term remedies and long-term solutions to end the experience of homelessness.


This is an extraordinary opportunity for a senior employment professional to join this team of 550 employees and make a difference in the lives of those less fortunate. Reporting to the Vice President of Human Resources, the Director, Employment and Workforce Planning will promote Pine Street’s new organizational focus and strive to develop and drive efforts toward enhancing its future human capital, effectively advancing the organization’s strategic plan and mission. The Director will lead the current hiring processes through a period of evolution, utilizing best practices in attracting, hiring, and retaining both passive and active candidates for employment or internship opportunities.

Core Responsibilities

  • Collaborate with senior managers to design, implement, and oversee workforce planning efforts in programs and administrative departments, including the creation of job analysis and other tools, to support hiring managers in designing optimal positions.
  • Design and implement an effective strategy to create partnerships with universities and other talent pipelines for employees and interns, resulting in an increased talent pool of both active and passive candidates.
  • Expand an already successful hiring and selection program through the advancement of current technologies, selection policies/practices/workflows, and training to hiring managers, resulting in the hiring of the most qualified candidates as rapidly as possible.

Human Resources Leadership

  • Possess and consistently model strong core ethics, integrity, and accountability consistent with Pine Street’s mission, vision, and values. Demonstrate discretion and professionalism for all staff at all times. Align and lead the work of the recruiting staff toward the mission, vision, values, strategic plan, and department and individual goals.
  • Lead and develop a staff of Recruiter, Contract Recruiter, and Receptionist in a manner that is diplomatic, inclusive, transparent, communicative, open, and fair. Provide opportunity for individual and professional learning and development. Create measurement tools to evaluate time-to-hire, turnover, candidate production, and support staff in implementing their use.
  • In partnership with HR colleagues, consistently identify, organize, promote, and operationalize approved opportunities to advance and/or streamline HR initiatives and operations in support of organizational and department goals. Inspire, develop, and manage change initiatives with recruiting staff and within the HR department in support of broader organizational goals.
  • Understand budget limitations and advocate for an environment where decisions are made in accordance with such limitations. Partner and collaborate with peers and management to facilitate cooperative business relationships with/between all programs and departments.
  • Provide visible and valuable participation in all Pine Street activities, including but not limited to general staff meetings, department staff meetings, human resource/agency events, and other celebrations.
Employment and Workforce Planning
  • Develop and continually evaluate/improve upon a recruitment plan to attract well-qualified, diverse staff both internally and externally. Manage and evaluate search partners and agency relationships.
  • Manage an experienced recruiter in their efforts to source candidates and administer the selection process. Consistently evaluate and streamline efficiencies and recruiting processes. Directly manage recruiting and hiring for select key positions.
  • Create, monitor, and distribute reports to leadership that measure success against recruiting goals, including time-to-hire. Establish metrics to deliver results to internal clients. Recommend appropriate recruitment methods and oversee training on recruiting, behavioral interviewing, and effective hiring.
  • Identify and collaborate with other HR colleagues and vendors to advance the use of technologies, including Clear Company Applicant tracking system, Skill Survey reference checking, and others.
  • Oversee the new hire selection process, and ensure that reference and background checks are completed appropriately and exponentially.
  • Oversee the management of the recruitment and advertising budget. Monitor and constantly work to reduce the costs of the recruitment process.
  • With recruiting staff, develop refreshed hiring policies and procedures for all supervisory employees which are compliant with all legal/regulatory obligations and utilize existing technologies.
  • Develop, implement, and oversee the workforce planning and requisition process, evolving current system to streamline approval process and elevate the supervisor’s abilities to analyze and create appropriate jobs and position descriptions.
  • In collaboration with the Vice President of Human Resources and other leaders, develop an overall strategy and implement a work-plan to increase outreach and networking through a wide range of sources to attract passive candidates, as well as advance and expand upon Pine Street’s internship program to grow direct care employment.
  • Provide guidance to supervisory staff around state and federal hiring guidelines.

Ideal Candidate

The Director, Employment and Workforce Planning will be a high energy, extremely motivated, and resilient self-starter who excels in a complex, dynamic environment and has successfully led a department or working unit of similar scope and size through change. The Director will have significant progressive management experience in talent acquisition and creating workforce planning programs.

Key Requirements 

  • Bachelor’s degree with a focus on human resources, business administration, or a related field. A Master’s degree with significant academic experience in psychology, sociology, or human services is preferred.
  • Professional certification in human resources (PHR, SPHR, etc.).
  • A minimum of seven (7) years of progressive human resources experience, including at least three to five years at management level or above.
  • Significant experience with and knowledge of optimal operations in a high volume recruiting environment.
  • Significant human resources experience in a human services, hospital, nursing home, or similar environment.
  • Project planning and management experience, as well as business process development experience.
  • Highly developed interpersonal, collaborative management, and organizational skills to enable successful relationships with leaders, managers, and supervisors, as well as front line staff and candidates of all levels.
  • In-depth knowledge of and experience with applicant tracking, applicant assessment, and applicant credentialing software, with significant experience in advancing the work of recruiting professionals.
  • Proven ability to make influential presentations and have influential discussions with individuals and groups to propel advancement of the presence of an organization’s employment brand in the marketplace and/or to attract top candidates.
  • Ability to work effectively with diverse populations to address difficult situations and solve complex issues.
  • Superior ability to adapt to competing and changing priorities, and handle information and situations with discretion and confidentiality.
  • Experience with or exposure to working with homelessness and conditions which affect homelessness is ideal.

Contact Karen Pappas Managing Partner
direct: 617-585-3038
mobile: 617-448-8896