Director of Human Resources Administration
Reports to: Chief Development & Operations Officer

About Chicago Scholars

Chicago Scholars is a 501(c)(3) nonprofit leadership development organization that empowers academically ambitious first-generation or low-income students to overcome systemic barriers to success in college and beyond while preparing the city’s businesses and organizations for the next generation of leaders.

Since 1996, Chicago Scholars has built a legacy of success by investing in our youth and amplifying their leadership. Our Scholars are high-achieving first-generation college students and students from low-income communities, and they have the talent, heart, and big dreams to become our next generation of leaders and transform our city. 

At its core, our work is about economic mobility, leadership development, and belonging. It’s about making sure our Scholars have everything they need to journey from Chicago’s classrooms to Chicago’s boardrooms—or to wherever their dreams may lead.

Chicago Scholars is transforming the leadership landscape of our city by resolving the fundamental barriers to success for academically driven, first-generation college students from under-resourced communities. Through college counseling, mentoring, and by providing a supportive community to our Scholars through each phase of our program: College Readiness, College Success, and Career and Leadership Advancement, we ensure that they realize their full potential as students and leaders.

76% of Chicago Scholars graduate college within 6 years. Per the University of Chicago Consortium on Chicago School Research, only 49% of their peers earn a degree within 6 years. Upon graduation, our Scholars move into leadership positions across Chicago, helping to drive the economic future of their communities and our thriving city.

READI Commitment 

At Chicago Scholars we strive to prepare our Scholars for the world and the world for our Scholars. Our dual focus on Scholars and the world is essential to our strategy. To achieve these goals, we center racial justice, equity, accessibility, diversity, and inclusion (READI) in all that we do. 

Chicago Scholars’ commitment to READI encompasses all of our stakeholders—from our staff to our board, from our volunteers to our partnering organizations, and most importantly our Scholars. This holistic approach is necessary for the sustained, long-term, positive impact that we seek for our Scholars, our neighborhoods, our city, and our world.

To learn more about Chicago Scholars commitment to READI, please visit chicagoscholars.org/readi.

At Chicago Scholars, we believe that education is social justice. That's why we're empowering Chicago's best and brightest first-generation college students and students from low-income communities with the mentors, resources, and opportunities to go to our nation's best colleges and universities, graduate on time, and become Chicago's next generation of leaders. Since 1996, we've impacted the lives of more than 5,000 young leaders in Chicago.

Our Values

These are a set of guiding principles that apply to all stakeholders within the Chicago Scholars ecosystem. We select and retain stakeholders based on these stated expectations for how we achieve our mission and vision. Each is supported with core competencies and narrative for the sake of clarity.

We Dream Big. We speak up, innovate, push the boundaries and keep the creativity flowing. We don’t accept the status quo because the stakes are too high. We have an incredible belief that growth and change is possible. While we dream big, we are laser focused on our intended goals and outcomes for our Scholars, our city and the world.

We Show Up. We show up every day; not just physically, but with a positive attitude and willingness to work, connect, challenge, engage, solve problems and have fun. We don’t wait for someone to tell us what to do. We take action and get the job done. If we don’t know how, we figure it out through our knowledge, exploration or our network.

We Embrace Our Differences. We represent a multicultural nation and our collective backgrounds, experiences, styles, values, perspectives and beliefs are an asset to the world. We recognize that together we achieve better outcomes more quickly. Justice and equity starts with us using our collective voice.

We Model the Way. We exhibit the behavior that we want to see in others and in the world. Titles are granted, but our behavior is what earns us respect. In order to model the way, we must be clear about our guiding principles, celebrate our accomplishments and learn from our challenges and failures.

We Care For Each Other. We adapt to the needs of the person in front of us. We pause, reflect and listen. We do our best work when we are in good relationship together. We care personally and challenge directly.

We Keep Our Word. When we commit, we are all in. Whether for events, a Scholar, a peer or ourselves. Our words are as powerful as our actions and are the building block of trust, respect, self-worth and integrity.

Position Summary

Chicago Scholars is seeking a strategic and execution-focused Director of Human Resources Administration to lead the operational foundation of our people function. This role oversees HR systems, processes, and administrative functions across the full employee lifecycle while ensuring compliance, consistency, and a strong employee experience.  This is a Director-level leadership role responsible for organization-wide HR operations, with oversight for both Chicago Scholars and REACH Pathways, L3C, a Chicago Scholars-owned entity with a standing shared services agreement for HR support. The Director partners with executive leadership while maintaining hands-on oversight of systems, compliance, and administrative processes.

Key Responsibilities

· Lead HR operations across recruitment, onboarding, lifecycle, and offboarding.

· Oversee benefits administration, payroll coordination, and compliance.

· Maintain HR systems (HRIS) and data integrity.

· Maintain up-to-date employee handbook, conducting annual internal audits.

· Develop policies, procedures, and audit-ready processes to ensure compliance with federal, state, and local legal requirements.

· Stay abreast of existing and new legislation, enforcing adherence to legal requirements, and advising management on needed actions to remain compliant.

· Lead Chicago Scholars efforts to be a “Best Places to Work”, including coordinating the annual employee surveys, supporting a culture of belonging and workplace for diverse talent.

· Support managers in performance management and employee relations.

· Regularly review applicant data to inform recruitment and cultivation strategy and share progress with hiring managers and executive team as applicable.

· Oversee the execution of the organizational training plan.

· Drive process improvements and operational efficiency.

· In collaboration with the members of the programming team, update and maintain current volunteer-related policies and procedures, including Mentor Handbook.

Additional Responsibilities

· Serve as the primary HR contact for REACH Pathways, tracking project hours on a weekly basis, to ensure support for the employee life cycle of the REACH workforce.

· As a member of the organization’s administrative matrix, support with management of weekly all-staff meetings, annual staff retreats, and office administration.

· This role will occasionally work on nights and weekends for Scholar and Development events and programming. This role is also required to attend and support mandatory all staff events. 

· Other duties, as assigned.

• Education: Bachelor’s degree; Master’s degree, or equivalent experience preferred 
• Experience: 5 to 10 years of relevant experience in HR systems
• Proven experience in Paylocity or Rippling
• Must live in the Chicagoland area

Core Competencies

• Values & Prioritizes Inclusion: Consistently sees, learns from, and takes strategic action related to diverse perspectives; and demonstrates self-awareness and behaviors to work with stakeholders respectfully and effectively.
• Accountability/Project Management: Effectively manages own work, and work of teams when relevant, ensuring delivery of high-quality work.
• Leadership Intelligences: Ability to meet people where they are at, treat them with respect, and influence them. Ability to effectively represent Chicago Scholars in any environment.
• Decision Making: Effectively structures and facilitates decision-making processes; makes decisions effectively and responsibly to improve organizational health and impact.
• Continuous Improvement Minded: Identifies strategies to improve organization’s impact; weighs diverse inputs to inform strategies; sets course and drives implementation.
• Teamwork/Collaboration: Demonstrates awareness and respect of cultural and individual values. Listens to ideas from others, even when different from own. Is careful to ensure all sides are heard reaching a conclusion. Shares time, energy and knowledge with others to ensure they can succeed.
• Change Management: Effectively prepares for and guides teams through changes, both small and large.
• Communication: Communication is the ability to read and interpret information effectively, clearly articulate a plan of action, and influence others by way of written and verbal mechanisms.
• Adaptability: Ability to operate flexibly in changing contexts and operating environments. Ability to manage change effectively to support teams and reach intended goals.

AI Literacy & Engagement
Our team leverages AI to augment human creativity and enhance impact. In this role, you will be encouraged to experiment with AI tools to improve your work and drive efficiency. We seek individuals who demonstrate curiosity about emerging technologies and are comfortable integrating AI into everyday tasks. You will proactively identify areas of friction in workflows where AI can improve speed, quality, or insight, while maintaining a strong understanding of data security, privacy, and ethical considerations in AI use.

Starting Salary: $90,000-$100,000

Best Offer First Policy: The data nationally show for every $1 paid to white men, women earn 82 cents, black men earn 88 cents, and black women earn 76 cents.  Women and black and brown people are also less likely to negotiate than their white male peers. Chicago Scholars has decided to offer our best offer first rather than wait for a potential negotiation. This allows us to set salaries based on market data and internal equity and ensure fair and equal pay for every role. 

If you have questions regarding either of the above policies, or any of Chicago Scholars employment policies, please reach out to the Human Resources team at humanresources@chicagoscholars.org with the subject line: Policy Question.

To Apply

Please click 'Apply' to submit your application which should include a resume and cover letter by 4 pm CST Friday, June 5, 2026. 

Please include a cover letter that explains your experience with being a one-person HR department in a nonprofit setting.