Associate Director HR Generalist

About Leading Educators

At Leading Educators (LE), we know that excellent teaching is the most important driver of student success. The moment a student steps foot in the classroom, their opportunity to learn depends on how prepared their teacher is to translate complex content knowledge, standards, and their knowledge of that student into lessons that help them learn deeply and apply their thinking to the real world. That’s a big lift, and it often happens alone. As a national nonprofit, we partner with school systems to overcome persistent instructional challenges, foster intentional collaboration and adult learning by design, and ignite new possibilities through systemic solutions at the intersection of teaching, talent, and technology. We work shoulder-to-shoulder with educators at every level of the education system to strengthen their instructional and leadership practices, bring a vision for excellent instruction to life with consistency, and ensure every student reaches their full potential. Through direct support, strategic advising, innovation pilots, and best-in-class research, we help educators work toward a future where every student is ready to thrive. Learn more about our work at leadingeducators.org.

Position Overview

The Associate Director, HR Generalist is responsible for executing the core HR operations that keep Leading Educators running smoothly. You'll own payroll processing, benefits administration, leave and accommodation management, multi-state tax compliance, HR compliance, and employee relations documentation across our organization. This is a high-precision, execution-focused role where accuracy is non-negotiable. Errors in this role directly impact employee trust, organizational compliance, and financial accuracy.

Key Responsibilities

• Own and execute payroll processing, ensuring employees are paid correctly and on time.
• Administer benefits, providing clear guidance to employees and precisely tracking elections.
• Manage leave cases (FMLA, ADA) with confidence, ensuring continuity of benefits.
• Execute multi-state tax compliance and employer setup, ensuring organizational compliance.
• Maintain HR records, ensuring they are audit-ready and aligned across systems.
• Prepare documentation for employee relations processes, including performance improvement plans and termination materials, with precision and consistency.
• Track employee relations cases and ensure all materials align with organizational standards.
• Serve as the primary point of contact for the People support inbox, responding to employee questions with clarity and timeliness.
• Identify process inefficiencies, recommend improvements, and refine workflows to reduce errors and increase operational speed.

What You Bring

• 5 to 7+ years of experience in HR operations, payroll, benefits administration, or HR compliance.
• Demonstrated experience managing payroll, benefits, and HR processes in a multi-state environment.
• Strong knowledge of HR compliance, including federal, state, and local employment laws.
• Experience managing leave and accommodation processes (FMLA, ADA, and related regulations).
• Strong attention to detail and ability to maintain accuracy across multiple systems.
• Ability to manage recurring operational workflows with consistency and reliability.
• Strong organizational and time management skills.
• Ability to handle sensitive information with discretion and accuracy.
• Strong written and verbal communication skills.
• Enjoy working with precision and attention to detail, especially under time pressure.
• Enjoy managing multiple recurring workflows and ensuring nothing falls through the cracks.
• Enjoy identifying patterns in operational issues and implementing process improvements.
• Enjoy learning and applying new tools—including AI-enabled workflows—to improve efficiency and reduce manual work.

Travel Requirements

This remote position requires 5 to 8 trips a year for org retreats, programming, job-related travel, or professional development. Your home office must be located anywhere within the U.S.

Benefits & Perks

• Base compensation range: $87,243 - $111,037 annually.
• Starting salary for this position: $99,140, with potential adjustments for significant relevant experience.
• 100% paid medical, dental, and vision coverage for individual employees.
• 60% employer contribution towards premium costs for partners and dependents.
• 4% matching 401k plan.
• Flexible Spending Accounts (medical, childcare, commuter).
• Employee Assistance Program (EAP).
• Accrual of 22 days of paid time off per year for the first three years, increasing to 27 days after the third year and 32 days after the sixth year.
• 22 additional paid holidays, plus three floating holidays.

Why Work at Leading Educators?

Imagine being part of an organization where your ideas and perspectives are highly valued. At Leading Educators, we believe in fostering individual strengths, encouraging personal growth, and embracing innovative ideas. If you thrive in a remote working environment, with the added excitement of travel, we're the perfect fit for you. By joining us, you become part of a powerful community of peers nationwide. Regardless of your location, you possess the power to make a significant impact on both students and teachers who rely on us daily. Join Leading Educators and become an integral part of driving progress in education.

Use of Artificial Intelligence in Hiring

We use AI-enabled tools to support administrative tasks and initial candidate reviews. All materials are human-reviewed, and all hiring decisions are made by people. AI is used as a support tool for efficiency and fairness.

Equal Opportunity Employment

Leading Educators is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ethnicity, religion, gender, sexual orientation, national origin, disability, age, marital status, military status, pregnancy, or any other characteristic protected by applicable local, state, or federal laws, rules, or regulations.

Key skills/competency

• Associate Director HR Generalist
• Payroll Processing
• Benefits Administration
• Leave Management
• Multi-state Tax Compliance
• HR Compliance
• Employee Relations
• HR Operations
• FMLA
• ADA