Director of Operations

Posted on: December 8, 2021 | |


Starting from fifty students in a three-flat in Chicago’s North Lawndale neighborhood in 2001, LEARN has grown into Illinois’ largest PK-8 charter school network. LEARN’s eleven schools in Illinois and Washington, D.C. serve more than 4,100 students, with a staff of 530 and an annual operating budget of $70 million.
LEARN’s students, 98% of whom are minority and 90% of whom are low income, have received national recognition for their accomplishments. 100% of LEARN graduates attend college prep high schools, including some of the nation’s top selective enrollment, private, and boarding schools. With 78% staff of color, LEARN prioritizes providing the youth of the communities it serves with a first-class education through an inclusive partnership with teachers, families, and the communities at large.

About the Opportunity

As the Director of Operations, you have the opportunity to serve as one of LEARN’s network-level Operations leaders, delivering best-in-class operations support to LEARN’s eleven schools. Reporting to the Managing Director of Operations, you will collaborate to build a team as well as creating and executing a strategy to drive operational excellence across all non-instructional functional areas — information technology, student enrollment,, food service, transportation, facilities and construction, data systems, and safety. LEARN runs a lean central administration; as such, the ideal candidate will be both a high-level/strategic and detail-oriented thinker and doer and thrive in an entrepreneurial environment.

Key Responsibilities and Outcomes

As the Director of Operations, your critical tasks will include:

Leading LEARN’s IT’s efforts;
Assist the Managing Director of Operations in providing cost-effective solutions that optimize LEARN’s ability to drive successful outcomes and experiences for students, by removing barriers for students, families, and staff.
Engage hands-on at LEARN facilities, which may involve supervising school arrival and departure activities, assisting with securing crucial classroom materials, and ensuring timely food service execution for students.
Help when and where needed; this may include helping principals, students, and other staff members in executing key priorities or directly aiding critical health, safety, and information technology teams.

Critical tasks will encompass:

Information Technology

Oversee Tech support for LEARN, including determining how LEARN should invest resources in terms of staffing and systems to boost support student outcomes.
Ensure consistent, reliable end user technology services are provided to all staff and campuses on a cost and time efficiency basis.
Optimize processes and operations of Network and campus technology infrastructure (e.g., LAN, network, telecom, related business operational systems). Manage data backup processes and disaster recovery plans. With Finance, develop and administer Network and campus technology budgets.
Plan and direct the rollout of large-scale technology equipment placements and desktop application upgrades.
Manage technology staffing through a combination of direct employees and contract personnel and budgets per the needs of annual technology plans and end-user break/fix needs.


Review and refine LEARN’s student enrollment policies and procedures; ensure LEARN’s accepted students are fully enrolled
Establishing enrollment target and managing SchoolMint (application system)
Setting up a full Enrollment calendar including lottery.
Implementation of the lottery and pre/post management.

Campus Support

Create training and best practices for campus support staff.
Plan and direct centralized procurement, maintenance and replacement of classroom furniture, furnishings and major supplies of student materials for all campuses.
Establish and monitor quality and performance of food service, student mass transportation and other purchased services for the campuses.
Negotiate costs, terms and conditions with suppliers. Conduct requests for proposals (RFPs) as needed. Create and implement service agreements and standards.

Safety and Security

Continually improve the safety of our schools through policies and strategic investments; develop and enforce security plans.

Facilities Operations and Security

Build annual operating and capital budgets based on feedback from various stakeholders and refine staffing plan.
Oversee aspects of functional operations for owned and leased facilities including space and site planning, construction management, regulatory compliance, and ongoing health and safety conditions/preventive maintenance plans.
Determine and oversee security procedures and staffing for all facilities.
Find and select service and equipment providers. Negotiate and enforce execution of vendor contracts. Manage relationships and lease fulfillment obligations by district and other school authorities from whom LEARN leases or shares facilities.
Optimize the efficiency and cost-effectiveness of LEARN facilities, including developing space reconfigurations to accommodate building population shifts.
Collaborate with LEARN’s Finance team; create and manage facilities and equipment operating budgets and capital replacement plans.
Work with LEARN Development team; conduct location/site due diligence and manage any facility expansions to LEARN’s building site portfolio.
Directly and indirectly manage site-based staffs of project manager(s), building engineers, security officers, and facility custodians. Covers all vendor-leased personnel and LEARN employees.

Required Qualifications

Education, Training and/or Experience

This position is a great fit if:

You have a bachelor’s degree
Strong IT knowledge and expertise
You can plan and execute simple to complex work practices and projects
You possess the ability to analyze and improve processes
You have a minimum of 5 years of project management leadership experience
You have a deep commitment to LEARN’s mission
You display high-level business acumen and judgment
You have strong negotiation skills and the ability to own major initiatives
You possess strong problem identification and solving abilities
You demonstrate experience with developing, documenting and implementing policies and procedures
You are familiar with and possess intermediate Google Suite proficiency

Preferred Qualifications

This position is an ideal fit if:

You have extensive knowledge and experience in IT
You are customer-service oriented with respect to both internal and external customers
You have a “get-it-done” mentality
You display the ability to prioritize and manage multiple projects
You have a collaborative mindset and proactively assist co-workers in accomplishing organizational goals
You possess a high degree of initiative and independent judgment
You can be flexible enough to work autonomously as well as take direction when needed
You are a tactful and effective communicator with all stakeholders

Time and Travel Requirements

Reach and work from any LEARN location efficiently and without hesitation. Our central office is located on the West side of Chicago, and our schools are located in Chicago, Illinois; cities north of Chicago (North Chicago/Waukegan); and Washington, D.C.
Occasionally respond to emergency issues that occur outside of normal business hours and for staffing occasional evening and weekend projects. A reasonable amount of flexibility to accommodate this need is an essential part of this position.


LEARN provides competitive salaries based on candidate qualifications and experience. LEARN strives to be among the best places to work in education, and our employee benefits are designed to support us in this ambition. We provide health, dental, life, and disability insurance, a 403(b) plan or access to the Chicago Teachers Pension Fund, paid time off, among numerous other benefits.
Diversity Commitment
LEARN is committed to partnering with the communities we serve and works to ensure that our staff reflect the great diversity reflected in our communities. LEARN’s policy requires that all applicants and employees be treated in a non-discriminatory manner without regard to race, color, national origin, ancestry, citizenship, religion, sex, age, marital status, sexual orientation, military status, disability, or any other characteristic prohibited by law.
Proof of full COVID-19 vaccination required of all applicants.