Director of People & Operations

Position Summary

Meals on Wheels Chicago is seeking a highly organized, systems-minded Director of People & Operations to serve as the operational backbone of our small, high-impact team. Success in this role means the CEO and team spend less time managing internal administration and more time advancing the organization's mission, programs, and revenue.

This role owns the internal systems and administrative functions that keep the organization running smoothly, from HR, payroll, and benefits, to financial administration, compliance, insurance, technology, and office operations. The ideal candidate is a proactive problem-solver who enjoys creating structure, anticipating needs, and finding smarter and more efficient ways to work.

Key Responsibilities

HR & People Operations

• • Manage onboarding/offboarding, personnel records, payroll coordination, and benefits administration.
  • Maintain HR compliance, required training, employee surveys, and annual HR requirements.
  • Coordinate recruiting administration and performance-review processes.

Finance & Compliance

• • Coordinate invoices and supporting documentation for final CEO approval and payment.
  • Liaise with the outsourced bookkeeper and CEO to support budgeting, financial projections, and audit preparation.
  • Manage organizational registrations, licenses and renewals, including City and State requirements and licensing.
  • Coordinate all insurances, cybersecurity coverage, and maintain contracts, and compliance records.
  • Maintain a master calendar of organizational deadlines and requirements.

Systems & Process Improvement

• • Own internal systems and continually identify opportunities for greater efficiency and automation.
  • Manage technology vendors, software, subscriptions, system access, and cybersecurity practices.
  • Develop and maintain policies, workflows and Standard Operating Procedures (SOPs).
  • Ensure organizational and stakeholder information is accurate and current across systems.

Organizational Operations

• • Manage office needs, equipment, vendors, subscriptions, and facilities.
  • Coordinate Board meeting logistics, records, and administrative needs.
  • Troubleshoot operational issues and build sustainable solutions.
  • Take ownership of administrative needs that would otherwise pull leadership away from higher-value priorities.
  • Create systems, documents that ensure consistent information for everyone involved in events and activities.
  • Review and plan for performance, programmatic and event-based needs.
  • Other duties and responsibilities may be added at the discretion of the CEO.

Qualifications

• • 4–6 years of experience in operations, HR administration, finance administration or nonprofit management; nonprofit experience preferred.
  • Strong organizational skills with the ability to independently manage multiple priorities and deadlines.
  • Comfortable working with payroll, benefits, invoices, budgets, and financial projections.
  • Technologically confident and interested in improving systems and workflows; Virtuous CRM experience is a plus.
  • Working knowledge of HR compliance, benefits and organizational risk.
  • Excellent judgment, discretion and attention to detail.
  • A proactive mindset, you don't simply maintain processes but you look for ways to make them better.
  • Excellent customer service skills
  • Valid drivers license
  • Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job. Duties, responsibilities and activities may change at any time with or without notice.

Benefits & Work Environment

We believe people do their best work when they have the support, flexibility and trust to thrive. Meals on Wheels Chicago offers a strong benefits package and a collaborative work environment that includes:

• Health, dental and vision insurance to support you and your family
• 403(b) retirement plan with employer contribution to help you invest in your future
• Generous paid time off and paid holidays because meaningful work should leave room for life outside of it
• Paid parental leave for employees welcoming a new child
• Flexible, hybrid work environment that values both in-person collaboration and the flexibility to work remotely
• Professional development support and opportunities to continue building your skills
• Autonomy and trust to take ownership of your work, improve how we operate, and make a visible impact
• A small, collaborative team where your ideas matter and your work directly contributes to improving the lives of older adults across Chicago