Director, People Operations

ABOUT SWING EDUCATION:

Founded in 2015 by former K-12 educators and administrators, Swing Education is a leading platform assisting school districts in sourcing dependable, highly qualified substitute teachers. Recently recognized as the Most Innovative Company in Education by Fast Company and named a Great Place to Work in 2024, Swing continues to set the standard for excellence in the EdTech space. At the core of our company stands a diverse and visionary leadership team. In the face of a nationwide teacher shortage, Swing believes that every classroom should have a teacher, and every student deserves uninterrupted learning. At Swing, we champion a fundamental belief: for our schools and students to thrive, our team must reflect the rich diversity of the thousands of students and educators we are privileged to serve. We are committed to creating a work culture that embraces inclusivity and belonging for every member of our present and future team.

This position is expected to operate in line with our Core Values:

• Deliver WOW to Schools and Subs
• Be Curious, Stay Curious
• Win as a Team
• Live Diversity, Equity, and Inclusion

POSITION SUMMARY:

The Director of People Operations will lead and execute core People Operations programs and processes that support a high-performing, mission-driven organization. This role owns the People operations strategy and leads the team responsible for onboarding, employee relations, payroll, benefits, compliance, total rewards, and performance management for both our corporate team and substitute teacher workforce across our active markets. The Director sets team priorities and maintains clear visibility into day-to-day operations, while building scalable processes and systems that can grow as the organization expands.Given the scale and complexity of our workforce, this role also ensures strong compliance practices and reliable People data. You will oversee multi-state employment compliance, workers’ compensation, unemployment, benefits administration, and 401(k) governance, while continuing to improve our HRIS and payroll platform, so our data and processes remain accurate and dependable.

This leader will partner closely with executive and functional leaders to ensure People Operations initiatives align with company priorities. The ideal candidate is a strong operator who is comfortable balancing strategy with hands-on execution in a lean environment.

ESSENTIAL DUTIES AND RESPONSIBILITIES:

People Strategy & Business Partnership

• Partner with executive and functional leaders to align People initiatives with business goals
• Support workforce planning and organizational design discussions in partnership with senior leadership
• Provide guidance on talent planning, performance management, and employee engagement
• Use data and insights to inform decision-making and improve operational effectiveness

Employee Lifecycle & Operations

• Oversee and optimize core People processes including recruiting, onboarding, performance management, engagement, and retention
• Ensure consistent and equitable practices across compensation, benefits, leave, and employee relations
• Lead execution of performance and talent processes that drive accountability and development
• Improve systems and workflows to create an efficient and scalable employee experience
• Adapt programs and processes to effectively support both corporate and substitute employee experiences at scale
• Expertise in full-cycle, multi-state payroll, compliance, reporting, and year-end processes

Compliance & Risk Management

• Ensure compliance with federal, state, and local employment laws and regulations
• Partner with Legal to manage employee relations matters and investigations
• Maintain and update employee handbooks, policies, and documentation
• Proactively identify and mitigate organizational risk
• Maintain compliance practices across multiple states and worker classifications, particularly as they relate to our corporate and substitute workforce
• Ensure audit readiness for 401(k) and related compliance reviews

Talent & Organizational Development

• Support hiring managers with effective recruiting and selection practices
• Implement manager training and development initiatives
• Drive engagement initiatives that strengthen culture and retention
• Champion inclusive and equitable practices across the organization

Systems & Analytics

• Oversee HRIS and People systems to ensure data integrity and reporting accuracy
• Track and report on key People metrics (turnover, engagement, hiring, performance outcomes)
• Identify opportunities to streamline processes and improve operational efficiency

Team Leadership

• Lead and develop a small, high-performing People Operations team
• Establish clear goals, accountability, and professional development plans
• Manage departmental planning and budget responsibly
• Model strong leadership presence and cross-functional partnership across the organization

REQUIREMENTS AND QUALIFICATIONS:

• Bachelor’s degree in Human Resources, Business Administration, or related field, or equivalent practical experience
• 7+ years of progressive HR or People Operations experience, ideally in a high-growth or scaling environment
• Experience leading core People programs and directly managing and developing People team members
• Strong working knowledge of multi-state employment law, employee relations, and HR best practices
• Track record of improving and scaling People processes in a fast-paced environment
• Demonstrated ability to balance strategic thinking with hands-on execution in a lean team
• Strong analytical and problem-solving skills, with comfort using data to guide decisions
• Excellent communication and stakeholder management skills
• Hands-on experience with HRIS platforms, preferably UKG
• Experience supporting high-volume or distributed workforces preferred
• Experience building and scaling People programs and infrastructure in a Series B to D or comparable high-growth environment strongly preferred
• SHRM-CP, SHRM-SCP, PHR, or SPHR preferred but not required
• Remote position; California-based candidates preferred

This position requires current authorization to work in the U.S. without employer sponsorship. Relocation assistance is not available for this role.