Chief Operating Officer

Start Date: August 2026

Type: Full-Time

Education: Bachelors and above

Language: English (Spanish a plus)

Location: Chicagoland – Woodlawn/Evanston

Salary/Wage: $125,000 - $150,000

Mission Statement

For Chicagoland youth who desire and deserve more, MetroSquash combines academic support, competitive squash, and enrichment opportunities to empower students to realize their potential and make their mark.

Overview

MetroSquash was founded in 2005 as an out-of-school time program for Chicago Public School students. The first MetroSquash class consisted of 10 fifth-grade students and utilized squash courts and classroom space at the University of Chicago. A grade level was added each year to realize a service pathway from 5th grade through post-secondary completion. In 2015, the organization raised over $8M to construct a permanent home - the 8-court Hussain MetroSquash Center in Woodlawn. With an operating budget of $3.5M, MetroSquash has 20 full-time staff serving over 500 students and their families annually. In 2018, MetroSquash opened its first satellite location in Evanston to serve students just north of Chicago. MetroSquash Evanston currently serves 70+ 6th-12th graders as well as college students and utilizes court space at the McGaw YMCA. The organization will embark on a $15M capital capital campaign in the fall of 2026.

Description

The Chief Operating Officer (COO) is an integral member of MetroSquash’s senior leadership team and serves as the organization’s primary internal operator. Reporting to the Chief Executive Officer (CEO), the COO is responsible for translating MetroSquash’s vision and strategy into strong, scalable execution across people, systems, and operations. Working across departments, the COO ensures that staff are well-supported, systems are effective and aligned, and the organization operates with clarity, consistency, and accountability. This role connects strategy to day-to-day execution, enabling MetroSquash to deliver excellent programs and strong student outcomes while scaling responsibly

Key Responsibilities

Organizational Leadership & Strategy

• Serve as a key member of MetroSquash's senior leadership team, partnering with the CEO and executive leaders to align people, systems, and resources in support of the organization's strategic priorities.
• Support professional development, coaching, and growth opportunities for leadership staff.
• Liaise with external partners (e.g., HR, payroll, and accounting firms) on HR-related matters.
• Provide direct supervision to designated senior leaders (e.g., Senior Director of Facilities & Civic Engagement).
• Partner with the CEO to assess and pilot effective staffing models across sites, Woodlawn and Evanston.
• Ensure consistency in job descriptions, supervision structures, check-ins, performance management, and organizational documentation.

Budgeting, Operations & Systems Management

• Partner with the CEO and the accounting team to design, execute, and monitor the annual operating budget, ensuring organizational resources are strategically aligned with programmatic priorities and goals.
• Oversee the management of cross-departmental budgets, establishing standardized monthly reporting templates and accountability frameworks that equip department leads to actively track and manage their budgets.
• Design, implement, and continuously improve operational systems across staff performance management, program delivery, scheduling, logistics, and internal controls.
• Ensure organizational policies, protocols, and the MetroSquash Handbook are clearly communicated, understood, consistently implemented, and regularly reviewed.
• Oversee organizational operations including internal calendars, safety practices, facilities coordination, and site-level logistics to support high-quality programming across locations.
• Clarify organizational roles,responsibilities, and workflows across departments to strengthen collaboration, reduce friction, and increase efficiency.

CRM Administration, Data Integrity, Reporting & Continuous Improvement

• Maximize the effectiveness of Salesforce and related systems for capturing, monitoring, and sharing programmatic and operational data.
• Develop and maintain executive dashboards that track organizational health, staff capacity, and student outcomes.
• Lead organization-wide data management initiatives, including staff training, data validation and cleanup, system implementation, and continuous improvement to promote data integrity and informed decision-making.
• Use data to support continuous improvement, strategic decision-making, and accountability.

Development, Grants & External Relations

• Collaborate with the Development team to translate grants, contracts, and restricted funding into internal action plans, budgets, and implementation timelines.
• Support grant compliance and reporting, including participation in funder meetings as needed.
• Contribute operational insights to board materials, committees, and leadership discussions.
• Partner with the CEO in articulating MetroSquash’s operational capacity, organizational performance, and execution progress to board members and external stakeholders.

Required knowledge, skills & abilities:

• A bachelor’s degree and 7+ years of increasingly advanced nonprofit operations experience
• Must have a minimum 3 years of supervisory experience.
• Strong knowledge and experience with Salesforce and similar CRM platforms
• A strategic thinker who enjoys building relationships.
• Motivated, self directed, and excellent at follow through.
• Highly organized, detail-oriented, and able to balance multiple projects at once.
• Excellent written, communication, and interpersonal skills, with the ability to engage with multiple stakeholders effectively.
• Professional experience in a youth-serving and/or out-of-school-time setting a plus
• Commitment to MetroSquash’s mission.

Vacation & Benefits:

A generous benefits plan, including health and dental coverage, retirement matching and 15 vacation days and 5 sick days in the first year.

English (Spanish a plus)