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Swing Education

Senior Human Resources Manager

Employment type
6 months ago
Remote - San Mateo, California

On average, U.S. students are with substitute teachers for 5% of the typical school year. That means our students have substitute teachers for more than six months of their K-12 school career. The problem? We're suffering from a national shortage of substitute teachers.

Swing Education is a tech startup based out of San Mateo, CA focused on tackling the substitute teacher shortage. We make it easy for great schools and quality subs to find each other. We help schools access more subs and offload tedious work (recruiting, screening, payroll, etc.) and we help subs find jobs, gain experience and build their professional network.
Swing is a revenue generating, Series C, YC company (through ImagineK12). To learn more about Swing visit

About the Position:
Reporting to our VP of People Operations, the Senior Human Resources Manager will serve as a business partner developing strategic human resource programs, processes and policies for the Substitute Teacher (W2) Workforce as well as oversee the day-to-day administration. This role is responsible for ensuring the “back office” elements of the Human Resources (HR) processes and procedures are accurate and compliant with internal policy and external regulatory requirements while striving for continuous improvement in the area of HR Operations and Substitute Teacher Performance Management. This position requires the ability to think strategically and tactfully, while also maintaining enthusiasm and a “roll up your sleeves” mentality.

This is a full-time position with the option for remote work. Swing Education’s office is located in San Mateo, California, however, all staff are working remotely during the COVID-19 pandemic until further notice.

Key Responsibilities and Activities:

HR Process Management and Execution:

  • Maintain relationships with legal counsel to stay ahead of changes to applicable employment regulations and HR compliance laws such as California’s Assembly Bill 5. Ensure all People Operations policies and procedures are updated and compliant with current state and federal legislation
  • Aligning with industry best practices, ensure efficient and repeatable processes are in place to manage the day-to-day HR transactions associated with hiring, onboarding, employee changes and off-boarding
  • Partner with the Product & Engineering and Customer Experience Teams to drive HR process improvements while ensuring ease and efficiency for all stakeholders


HRIS, Audits and Reporting:

  • Develop reporting and/or dashboards that deliver meaningful information to senior management and key business stakeholders to effectively evaluate HR metrics
  • Establish systems and processes to ensure timely and accurate maintenance of HRIS data 
  • Partner with the Finance Team to accurately track and report on labor related metrics (i.e. headcount, costs, etc.). 
  • Partner with Customer Experience Team to ensure payroll-related processes are in place and meet standard auditing protocols


Benefits Administration and Compliance:

  • Vendor management for all of Swing’s vendor partners for the Substitute Teacher workforce including ADP (HRIS/Timekeeping/Payroll), I9Everywhere (Form I-9), insurance broker and health and retirement providers (Benefits Administration)
  • Provide guidance on pertinent federal and state regulations, filing and compliance requirements including COBRA, FMLA, ADA, OSHA and EEO
  • Establish sound relationships with benefit broker(s) and service providers to enable rapid response to issues and questions as needed
  • Coordinate health insurance enrollments with service providers concerning the routine administration of programs
  • Ensure compliance with COBRA guidelines by coordinating with a third-party administrator
  • Plan and administer Workers Compensation program and oversee and/or file claims as needed and ensure documentation and records are maintained
  • Establish, monitor and administer accurate and timely leave of absence procedures, ensuring clear and accurate communication to the impacted employee and coordinate timely and accurate payroll and leave details to Payroll and related service providers
  • Keep up-to-date on HR compliance requirements and implement updated and/or new internal compliance processes as needed
  • Manage the development and submission of timely and accurate compliance reporting, actions and/or record administration to include, but not limited to EEO-1, Vet-100, 5500’s, SPDs, I-9 records, ACA reporting, Sexual Harassment Prevention training, etc.
  • Partner with the VP of People Operations to support the annual review and renewal of benefit programs


Performance Management and Employee Relations:

  • Provide an effective and dedicated HR advisory service to employees, and other Swing teams, in relation to absence issues, conduct and capability, grievances, and all other employee-relations matters of the Substitute Teacher (W2) Workforce
  • Partner closely with the Customer Experience Team to ensure Substitute Teacher Performance is managed to expectations. Provide coaching and guidance on a variety of employment matters such as performance management, employee relations, risk and compliance
  • Conduct investigations and research employee complaints; serves as liaison with outside legal counsel on HR related legal issues
  • Plan and conduct involuntary employment terminations


People Management and Development:

  • Supervise the HR Generalist for the Substitute Teacher Workforce to ensure the timely, accurate and efficient execution of the Human Resources activities
  • Coach, develop and provide actionable feedback to ensure optimum performance and ongoing development


  • 5 - 7 years professional HR operations experience ensuring employment law compliance for California workforce, including 3+ years of management experience
  • Strong knowledge of California and U.S. Federal labor/employment laws required
  • Experience working with a multi-state workforce strongly preferred
  • HRIS experience with understanding of HRIS systems design, HR reporting, workflow, and auditing requirements. ADP Workforce Now and eTime experience preferred
  • Bachelor’s Degree in Business Administration, Human Resources, or related field preferred
  • PHR or SPHR certification desired
  • Passion for people operations and desire to continuously improve and scale HR processes and programs
  • Experience discerning and escalating matters of significance to senior leadership or outside counsel
  • Excellent project management skills with exceptional attention to detail and discipline to organize and prioritize
  • Self directing, able to work with minimal supervision
  • Ability to build effective work relationships at all levels of the organization, and partner cross-functionally to influence behavior change and collaboration
  • Comfortable as a “hands-on” manager; willing to roll up your sleeves to get things done
  • Strong problem solving and critical thinking skills while exercising sound judgement
  • Ability to perform in a fast paced, dynamic environment, and manage multiple priorities
  • Must be able to act in an ethical manner and maintain highly confidential and proprietary information



  • Salary is commensurate on experience and is adjusted for cost of living standards dependent on position location. Swing Education offers a comprehensive benefits package which includes the following perks:
  • Medical/dental/vision benefits
  • Generous PTO
  • Paid holidays
  • Family leave
  • Stock options
  • Professional development reimbursement program
  • Mission-driven work
  • Fun, collaborative, balanced culture


Swing Education is an equal opportunity employer and strongly encourages applications from people of color, persons with disabilities, women, and LGBTQ+ applicants.


To apply

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