Chief Operating Officer

Status: Full-time / Exempt

Reports to: Chief Executive Officer (CEO)

Direct Reports: Human Resources Manager, Senior Director of People & Culture, Director of Environmental Services, IT Specialist, Finance Manager (Contracted)

Organizational Overview

For over 30 years, The Boulevard has provided medical respite to individuals experiencing homelessness who are ill or injured, providing them with a place to restore their health, break the cycle of homelessness and rebuild their lives. The only facility of its kind in Illinois, The Boulevard’s west-side medical respite program provides a nurturing home for 150-200 adults a year. The program includes access to an on-site health clinic, full-service case management, housing and employment services, and everything our residents need to recover. In addition to medical respite, The Boulevard provides case management and housing support services to an additional 250-300 individuals and families located throughout Chicago each year.

Position Summary

The Chief Operating Officer (COO) is the senior executive leader responsible for translating organizational strategy into operational execution across programs, administrative functions, and multi-site service locations. The COO ensures operational excellence, compliance, high-quality service delivery, and measurable outcomes while supporting organizational growth and mission impact. The leader combines strategic oversight with a hands‑on leadership style, ensuring operational plans are executed with precision, speed, and accountability across all functional areas.

Key Responsibilities (Total: 100%)

Strategy & Organizational Leadership (30%)

• Convert strategic priorities into clear operational plans with defined metrics.
• Provide strong day-to-day operational leadership and serve as an advisor to the CEO and Board committees.
• Lead cross-functional initiatives driving efficiency, quality, and organizational resilience.
• Lead operational systems, administrative infrastructure, and internal workflows.
• Establish operational policies, standards, and processes that support efficient execution.
• Manage contracts, insurance review, and organizational risk management practices.
• Help strengthen internal systems and operational processes that support efficient program delivery.
• Provide leadership. visibility into operational capacity, performance, and emerging risks.

Executive Partnership (20%)

• Serve as a strategic advisor to the CEO on operational matters.
• Coordinate cross-functional initiatives and leadership priorities.
• Track key organizational initiatives and support follow-through.
• Assist the CEO with Board preparation, leadership planning, and strategic discussions.

Financial & Resource Stewardship (20%)

• Partner with leadership on annual planning, budgeting, and organizational priorities.
• Translate strategic priorities into operational goals, timelines, and accountability structures.
• Oversee financial operations in partnership with the contracted Finance Manager and the Finance Committee.
• Review financial reporting and operational metrics to identify trends and risks.
• Prepare operational and financial materials for Board and committee meetings.
• Review financial performance, manage expenses, and ensure grant/contract compliance.
• Identify opportunities for cost efficiency.

People & Culture (10%)

• Oversee HR policies, benefits administration, and compensation philosophy including pay equity review.
• Lead initiatives that strengthen organizational culture, performance, and retention.
• Ensure compliance with labor laws and sound judgment in personnel matters.
• Lead initiatives that support employee engagement and organizational health.
• Support workforce planning and leadership development.
• Guide managers on people-related matters and organizational practices.

Facilities & Operational Infrastructure (10%)

• Oversee facility operations across all sites, ensuring safety and compliance.
• Lead long-term capital planning and vendor management.

Technology & Data Infrastructure (5%)

• Oversee IT systems, electronic platforms, digital security, and reporting systems.
• Oversee systems integration projects.
• Lead digital transformation and data analytics initiatives.

Compliance, Quality & Risk Management (5%)

• Work closely with the Chief Program Officer to ensure adherence to healthcare and human-service regulatory requirements.
• Lead enterprise risk management and business continuity planning.
• Direct quality improvement initiatives using data-driven methods.

Qualifications

• Bachelor’s degree preferred.
• 5+ years of operations or organizational leadership experience.
• 3–5+ years of nonprofit experience preferred.
• Experience managing organizational systems and internal operations.
• Familiarity with CRM systems (DonorPerfect preferred), financial reporting systems (QuickBooks preferred), electronic health record systems (InSync preferred) and HRIS and Payroll Systems (ADP WorkforceNow and Employee Navigator preferred).
• Strong leadership, strategic thinking, and problem-solving skills.
• Ability to communicate operational or financial information clearly to leadership and board members.
• Experience working effectively in remote or hybrid teams

Compensation

• Salary range: $110,000 – $125,000, commensurate with experience and geographic location.
• This is a leadership-level role within The Boulevard of Chicago with significant organizational impact.
• The Boulevard is committed to competitive nonprofit compensation and a flexible remote work environment that supports employee well-being.

Benefits

• Medical, dental, and vision insurance
• 401(k) retirement plan with immediate eligibility
• $50/month remote work stipend
• Eligibility for Public Service Loan Forgiveness (PSLF)
• 15 vacation days annually
• 10 paid holidays
• Sick leave and bereavement leave

Equal Opportunity Employer

The Boulevard of Chicago is an equal opportunity employer and does not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, or any other protected status under applicable laws. We encourage individuals from all backgrounds to apply.

At-Will Employment Disclaimer

This job description is not intended to be an employment contract. Employment with The Boulevard of Chicago is at will and may be terminated by the employee or the organization at any time, with or without cause or notice.

How To Apply:

• • Submit resume to: recruiting@blvd.org
  • Please write your name (Last, First) in the subject line of the e-mail.
  • No phone calls please