Deputy Director

Job Type

Full Time


Minimum: $50,000
Maximum: $60,000




1955 North Saint Louis Avenue
United States


Background: CCL’s vision is a community where everyone thrives. Too often, lack of resources and economic opportunity limit participants’ choices and capacity to achieve their goals and vision. CCL partners with those held back by lack of resource and economic opportunity in order to uncover possibilities, overcome barriers, and realize their potential. Partnership takes many forms including coaching, training and educating, advocacy and organizing as well as coalition building are the primary ways that goals and potential are realized. 

Position Overview: The Deputy Director (DD) coordinates all programming and operational functions, oversees implementation of CCL’s strategic plan as it relates to program design, implementation and evaluation. The DD will operationalize best practices in management systems, including appropriate integration and collaboration of teams and varying areas of work, to ensure strong organizational performance to meet ambitious goals. The DD is responsible for maintaining a high-functioning, diverse, inclusive, and collaborative environment. An essential job function includes providing effective program operations management, managing personnel and financial resources to effectively reach program objectives. This involves day-to-day leadership and management that is in alignment with CCL’s mission and core values, including direct supervision and support of managers/coordinator for program design, development, implementation, evaluation, data management, reporting and strategic enhancements to programming itself. The DD will supervise and work with managers/coordinator to deliver measurable, efficient results that make the vision a reality. The successful DD will have the skills, sensitivity, and aptness to tap into the power that each member of the team brings to this mission.

While it is essential that the DD brings efficient and effective systems to increase the productivity of the organization, it is also critical that the team retain the creative spark that drives the CCL’s innovation. Moreover, the DD is responsible for all programmatic and operational functions, leading the high-quality implementation, evaluation, execution and sustainability of all CCL programs and operations. The DD will ensure that CCL has the proper operational controls, administrative and reporting procedures, and systems in place to effectively reach the organization’s goals and foster financial strength and operating efficiency.

As part of the senior leadership team, the Deputy Director will work to ensure that CCL is equipped with the tools, resources and insights to deliver on its mission. The DD is responsible for program administration that will include budget management in consultation with the Executive Director, comptrolling consultants and program managers. DD will manage staff supervision and compliance with appropriate program standards such as certification and contract requirements.

Reporting to the Executive Director of the CCL, the Deputy Director will lead all internal operations and will have the following areas of work:

Program Oversight and Human Resources Management

●       Coordinate with management team on all integrated programming to enhance stability of households served: 

o  Supervise program managers for performance management including coaching, mentoring and managing delivery of critical milestones on an ongoing basis to ensure programmatic and team success, as well as to support the team’s ongoing professional development and growth

o  Monitor the quality of program outputs and outcomes

o  Monitor client/staff/volunteer interaction to ensure the quality of services provided, including the use of coaching approaches, motivational interviewing and client empowerment strategies

o  Support staff teams in planning and implementation of critical, agency wide projects as needed

o  Oversee program evaluation

o  Monitor reviews of data and compiled reports on performance and program accomplishments for private and public sources of funding

o  Meet regularly with managers/coordinator and when needed, work together to find ways to standardize, improve and expand programs/services

o  Review quarterly and annual service delivery outcomes evaluation and reporting and contribute to the development of the annual report

o  Conduct meetings with staff and arrange for professional development opportunities

o  Oversee allocation of staffing resources and responsibilities for the agency’s collective priorities

o  Monitor system for client feedback and incorporation of feedback into program design and service delivery

o  Serve as the primary point of contact for program staff, conduct staff evaluations, resolve grievances and disputes as necessary

o  Responsible for HR management system, Zenefits, and for benefits administration and HR related files

o  Review and monitor adherence to personnel policies and procedures

Operations Management

●       CCL’s Strategic Operational Functions Related to Service Provision:

o  Manage all internship relationships with university programs, including the University of Chicago’s Social Service Administration School, Loyola’s School of Social Work and others.

o  Contribute to the development of agency staff meetings and agendas and professional development

o  Assist in writing program descriptions for grants and funding requests

o  Oversee program budget and maintain appropriate controls with expenses carefully considered, correctly coded, and within budget parameters

o  Provides program reports for board meetings

o  Works closely with the senior leadership team to communicate programming status, outcomes, successes, challenges, timelines, finances and direction

o  Act as a sounding board with the senior leadership team for ideas and strategic matters

o  Keeps lines of communication open ensuring that the senior leadership team is well informed and prepared for meetings, events and other activities

o  Collaborate with the leadership team on financial and operational performance, ensuring the office is efficient, effective and meets the overall objective of the agency in finance, administration and HR practices and are in line with CCL’s organizational standard operating procedures

o  As needed, represent CCL at external meetings, conferences or events

o  In coordination with the senior leadership team, prepare operational budgets

o  Ensure all staff members, volunteers and interns receive orientation and appropriate training in accordance with organizational standards

o  Review and monitor adherence to agency policies and procedures and applicable federal and state employment laws to ensure effective and efficient functioning of the agency

o  In conjunction with staff, engage in long-term planning, including initiatives geared towards operational excellence

Facilities and Technology Management

●       Accountable for the provision of a safe, secure, high quality environment for staff, volunteers and members served:

o  Execute and maintain a well-structured emergency plan, ensuring that staff, volunteers are properly trained responders

o  Accountable for all office space specific maintenance contracts and agreements, inclusive of development of annual maintenance calendar

o  Participate in team meetings, develop and execute additional projects as requested

o  Track and order organizational and program inventory and office supplies, ensures that all machines are maintained in good working order and sufficient supplies are at hand to ensure smooth operations

o  Oversee vendor selection and relationships; negotiate and manage vendor contacts

o  Analyze the current technology infrastructure and scope out the next level of information technology that support the growth of specific programs and the organization overall

Performs other duties as assigned.


The position is an outcomes oriented position, with specific expectations around the efficiency and effectiveness of operations and service provisions provided at CCL. Therefore, the Deputy Director is ultimately responsible for the CCL’s placement, retention and net income increase goals shares integrated service delivery outcomes on an annual basis. All staff are expected to set goals that outline reasonable improvements in outcomes and integration on an annual basis.

Working Conditions:

The position requires flexibility in schedule, duties, or unexpected events/circumstances that may occur, so tasks not specified here may be required to successfully execute the position and may be asked upon by Executive Director. Evenings and weekends and off-site work are required. The schedule is flexible and is subject to the needs of organizational operations. This position is supervised by the Executive Director.

Successful Candidate will Demonstrate:

●       Passion for CCL’s mission and its core values of innovation, poder, economic justice, solidarity and accountability

●       Strengths around creativity, resourcefulness, persistence and self-reflection

●       Proclivity to risk-taking and a willingness to fail, learn and adapt

●       Preference towards a non-directive, client and staff-led relationship

●       Openness to a no wrong door, employment/housing-first models that builds employment and financial capacity in clients with limited work history or multiple barriers to employment/housing

●       Openness to regular, 360 degree feedback and an environment of mutual accountability

●       Ability to engage a diverse community of people

●       Commitment to confidentiality and professionalism

Required Qualifications:

●       At least ten years of cumulative experience in housing, employment, financial or supportive service programs

●       At least seven years of supervisory experience, training in supervision strategies preferred

●       Sector knowledge related to housing, workforce and financial capability and understanding of the homeless service system

●       Knowledge of empowerment models of client engagement, including coaching and motivational interviewing

●       Experience engaging economic empowerment and affordable housing advocacy issues

●       Excellent verbal and written communications skills and abilities to facilitate meetings and train staff

●       Well-organized and detail oriented, able to think strategically and plan accordingly

●       Strong technology-related skills including familiarity with Microsoft Office and ability to navigate the internet

●       Excellent relational skills, cultural competency and ability to engage a diverse community of people

Preferred Qualifications:

●       Bilingual (Spanish/English) skills

●       Master’s degree in social work

Accountability: The Deputy Director is mutually accountable to CCL senior leadership team and program staff team; is supervised by the Executive Director, and interfaces with board as necessary.


This is a full-time (40 hours a week) exempt position that includes health and dental insurance, life, short term and long term disability insurance and generous paid time off.  

Professional Level


Minimum Education Required

4-year degree

How To Apply

Interested parties may e-mail their cover letter and resume to No calls please.