Senior Director of Human Resources

About One Million Degrees: 

One Million Degrees accelerates community college students’ progress on career pathways to economic mobility. 

Over 60% of students who start community college do not complete a degree or successfully transfer to a four-year institution. However, 84% of jobs in the US require skills training beyond high school. OMD’s holistic support model is designed to support community college students as they work toward degrees and careers. From tutors and coaches to financial assistance and professional development, OMD helps community college students succeed in school, work, and life, transforming their futures and the futures of those around them for generations.  

The OMD student support model is rooted in evaluation and evidence: A randomized controlled trial conducted with the University of Chicago Inclusive Economy Lab shows that OMD scholars are 70% more likely to enroll, 94% more likely to persist, 73% more likely to earn a degree.  

Currently, OMD serves scholars in all 7 of the City Colleges of Chicago (CCC) and is scaling to reach over 3000 community college scholars by 2026 through our unique partnership with CCC. In addition to direct services, OMD partners with employers across industries to build on-ramps to in-demand jobs through internships and apprenticeships and supports institutions nationwide to design and implement models of holistic student support. 

Through this growing body of work, OMD continues to have a profound impact in Chicagoland while becoming a national model for sustainable, scalable, and systemic change.  

OMD Values: 

OMD is deeply committed to our core values, as demonstrated in the work we do, our approach to change and growth, and our commitment to our staff.  

• Equity: We address historical and existing systemic inequities by taking a holistic approach to supporting students on their path to economic mobility. 

• Excellence: We hold ourselves to a high bar and provide exceptional support so that students are empowered to achieve their ambitions. 

• Community: We unite around putting students first, collaborating with partners, and celebrating our collective wins. 

• Learning: We each adapt to a changing world and refine our approach to support students, community members, staff, and stakeholders along the way. 

• Amplify: We advocate for our students and share what we've learned as leaders in the field. 

Position Summary: 

The Senior Director of Human Resources is a critical leadership role responsible for overseeing all aspects of the organization’s HR function, including payroll, benefits administration, HR policies and procedures, labor relations and union communication, employee and manager training, and regulatory compliance. As a key member of the Leadership Team, this individual will actively contribute to strategic planning, organizational decision-making, and overall operational effectiveness within the non-profit. Operating in a hybrid work environment, this role requires a leader who can effectively support, engage, and build culture across both in-person and remote teams. This position calls for a hands-on, “roll-up-your-sleeves” approach, balancing day-to-day execution with the ability to think strategically and drive long-term initiatives. The Senior Director of Human Resources will report directly to the Chief Finance & Operations Officer and serve as a trusted advisor on all people-related matters. 

What You’ll Oversee & Own: 

Specific duties and responsibilities include but are not limited to: 

HR Strategy & Leadership 

• Lead, develop, and support the HR team; set priorities and provide coaching and mentorship 

• As an active member of Leadership Team, help establish organizational strategy and policy 

• Align HR initiatives with organizational goals and mission 

 Talent & Organizational Development 

• Oversee recruitment, hiring, onboarding, and offboarding 

• Lead all performance management systems and processes 

• Support leadership development and succession planning 

Employee Learning & Development Strategy 

• Define the strategic vision for employee learning & development, aligning training and professional growth with organizational priorities 

• Establish systems, tools, and processes to sustain ongoing employee learning, knowledge sharing, and continuous improvement 

• Lead the ongoing development of an organization-wide knowledge-sharing platform 

• Develop metrics to evaluate adoption and effectiveness of employee training programs 

Compensation & Benefits 

• Oversee compensation philosophy, benchmarking, and pay equity analyses 

• Design and manage employee benefits programs; lead annual employee benefits renewals 

• Manage employee classifications and ensure compliance with wage and hour laws 

Employee Relations, Labor & Compliance 

• Serve as primary point of contact for union relations and all ongoing engagement with union leadership 

• Ensure compliance with federal, state, and local employment laws and regulations 

• Develop, maintain, and enforce HR policies and the Employee Handbook 

• Address employee relations matters and foster a positive, supportive, compliant workplace 

HR Operations, Systems & Analytics 

• Oversee HRIS/payroll systems, including optimization, system enhancement, and process improvement 

• Lead HR data management, reporting, and analytics to support informed decision-making 

• Ensure accurate, timely, and thorough maintenance of employee records and documentation 

• Drive process improvements to enhance efficiency and cross-functional collaboration 

What Success Looks Like: 

A successful employee in this role will:  

• Lead the HR team in consistently producing accurate work and organized documentation 

• Ask thoughtful questions and show initiative in learning OMD processes 

• Be comfortable providing exceptional training to employees and managers  

• Maintain strong working relationships with employees across all OMD departments  

• Maintain strong working relationships with OMD’s employee union 

• Demonstrate reliability, accountability, and a commitment to punctuality  

• Contribute to a culture of collaboration and problem‑solving 

Qualifications and Requirements: 

Education and Certifications 

• Bachelor’s degree, ideally in an HR-related field 

• Senior-level HR certification such as SHRM-SCP or SPHR preferred 

• Additional certifications in compensation, benefits, or labor relations a plus 

Experience and Skills 

• 10  years of progressive HR experience, preferably in a nonprofit environment 

• Proficiency in payroll and cloud-based HCM software; OMD currently uses Paycom 

• Multiple years of leading and managing employee benefits renewal cycles 

• 6  years of managing highly successful HR teams and functions 

Traits and Competencies: 

• Strong attention to detail and excellent organizational skills 

• Demonstrates effective time management and reliably meets all deadlines  

• Exceptional communicator who listens well and relates to staff across all job functions 

• Collaborative team player with a commitment to OMD’s values of equity, excellence, community, learning, and amplification. 

• Ability to manage multiple priorities in a dynamic, fast-paced environment 

Compensation and Benefits for Full-time Employees:  

• Salary – $96,700 - $125,000 annually*  

• Full Health Benefits – Provided for all full-time employees, including medical, dental, and vision. OMD currently offers some medical insurance on which OMD covers 100% of individual’s monthly premium and 90% of monthly premium for employee  dependents.   

• Employee assistance program, which offers confidential emotional support, work-life solutions, legal guidance, financial resources, and more. 

• Retirement Benefits – For full-time employees, OMD offers a 401(k) plan and matches retirement contributions up to 4% of total salary.  

• Generous Paid Time Off Policy– OMD has 12 paid holidays and offers up to 15 days PTO in year one; in addition to two weeks paid time off for winter break (note: 3 of the 12 paid holidays occur during those two weeks at winter break).   

• Compensatory time for certain designated duties performed outside of normal work hours**  

• Monthly cell phone and internet reimbursement up to $50/month.  

• 12 weeks of paid parental leave for birthing and non-birthing parents.   

• Professional Learning Opportunities – OMD supports employee development in areas relevant to professional and organizational goals.  Annual Professional Development allowances are set as part of annual budgets, and employees have opportunities to seek occasional additional support  to supplement their personal Professional Development allowance when appropriate.  

• Hybrid Work Schedule – This senior role is expected to be onsite at OMD’s downtown Chicago office, or at a City College campus with OMD staff, at least two days each week; weekly onsite requirements can vary by position and by other considerations, will be established at manager’s discretion  

* To allow OMD to set salaries based on market data and internal equity, and to ensure fair and equal pay for every role, we provide our best offer first.  

**All employees are expected to work five Saturday mornings, and certain evening hours, each year due to organization-wide events.  

One Million Degrees is an equal opportunity employer. We encourage applications from all individuals regardless of age, gender, race, ethnicity, religion, or sexual orientation, and evaluate all candidates based on merit.