Senior Manager, Benefits and People Operations (Remote)

Job Description

Job Description

Description

Be a Part of our Team!

Join a working team that is dedicated to the mission of the work we do!

Teaching Strategies is an innovative edtech organization focused on connecting teachers, children, and families. As front runners in the early childhood education market, we build dynamic, top-quality digital products that integrate all of the essential elements of a high-quality solution: curriculum, assessment, professional development, and family engagement. We are building a team of results-oriented individuals who will thrive in a collaborative, work-hard/play-hard culture. We pride ourselves on the impact we have on the early childhood field through supporting teachers who are doing the most important work there is, teaching children to become creative, confident thinkers.

Position Overview

The Senior Manager, Benefits and People Operations is responsible for managing the day-to-day operations of the company's employee benefits programs, HR systems, people analytics, and operational processes that support the employee experience.

This role serves as the primary owner of benefits administration while also supporting broader People Operations initiatives, including HRIS administration, workforce reporting, compliance, process improvement, and operational support. The People Operations Manager partners closely with brokers, vendors, Finance, Payroll, and internal stakeholders to ensure programs are administered efficiently, compliantly, and with a strong employee experience focus.

The ideal candidate is highly organized, analytical, customer-focused, and capable of translating complex data
and processes into meaningful insights and solutions.
Specific Roles & Responsibilities:

Benefits Administration & Total Rewards

• Oversee the daily administration of the company's health and welfare programs, including medical, dental, vision, life insurance, short-term disability, long-term disability, flexible spending accounts (FSA), health savings accounts (HSA), and retirement programs.
• Serve as the primary operational owner of employee benefit programs and ensure efficient and compliant program administration.
• Partner with brokers, carriers, vendors, and internal stakeholders to maintain competitive and effective
  benefit offerings.
• Act as the primary escalation point for complex employee benefit questions and issue resolution.
• Ensure compliance with applicable federal, state, and local regulations, including ERISA, ACA, COBRA, HIPAA, and other benefits-related requirements.
• Monitor regulatory changes, assess organizational impact, recommend actions, and implement necessary updates.
• Manage monthly benefit billing, reconciliations, audits, and vendor reporting.
• Lead benefit plan renewals, annual open enrollment activities, employee communications, and
  implementation of new benefit programs.
• Configure and maintain benefit plans within the HRIS system.
• Partner with brokers and vendors to review utilization, claims, and program performance and provide
  recommendations for continuous improvement.
• Support budget planning by providing benefits data, analysis, and insights.
• Support the organizations compensation programs by conducting market pricing and benchmarks to ensure compensation remains competitive and aligned with business objectives.

People Operations

• Support the overall administration and continuous improvement of People Operations programs, processes, and systems.
• Serve as a key administrator for the company's HRIS platform, ensuring data integrity, system accuracy, and efficient workflows.
• Partner with Payroll and Finance to support employee lifecycle transactions and payroll-related processes.
• Develop and maintain standard operating procedures, documentation, and process improvements.
• Identify opportunities to streamline and automate People Operations processes to improve efficiency and employee experience.
• Provide guidance and support to People Operations team members on complex employee issues, policies, and procedures.

People Analytics & Reporting

• Develop and maintain People Operations dashboards, reports, and workforce metrics.
• Track and analyze key people metrics, including headcount, turnover, retention, recruiting activity, benefits utilization, compensation, and employee demographics.
• Translate workforce data into meaningful insights and recommendations for People Team and business leaders.
• Support monthly, quarterly, and annual reporting requirements.
• Assist with workforce planning, budgeting, and organizational reporting initiatives.
• Ensure accuracy and integrity of employee and organizational data.

Vendor Management & Compliance

• Manage relationships with benefit providers, brokers, retirement vendors, and People Operations partners.
• Coordinate vendor implementations, renewals, audits, and ongoing performance reviews.
• Support internal and external audit requests related to benefits, HRIS, and employee data.
• Maintain compliance documentation and ensure operational readiness for audits and regulatory reviews.

Team Leadership

• Provide day-to-day leadership, coaching, and support to direct reports.
• Establish goals and priorities for the People Operations team.
• Foster a culture of accountability, service excellence, continuous improvement, and collaboration.
• Support professional development and growth opportunities for team members.

Qualifications:

Required

• 5–7 years of progressive Benefits and People Operations experience.
• 5+ years of experience overseeing employee benefit programs.
• Previous manager experience acting as both a player and coach
• Experience managing health and retirement plans, and vendor relationships.
• Experience administering self-funded medical plans.
• Experience working with HRIS systems and employee data management.
• Strong analytical, reporting, and problem-solving skills.
• Experience managing complex employee issues with professionalism and discretion.
• Prior leadership or supervisory experience.

Preferred

• Experience with Rippling or other HRIS platforms.
• Experience supporting a multi-state workforce.
• Bachelor's degree in Human Resources, Business Administration, Finance, or a related field.
• CEBS, SHRM-CP, SHRM-SCP, PHR, or SPHR certification.
• Experience in a SaaS, technology, or high-growth organization.

Why Teaching Strategies

At Teaching Strategies, our solutions and services are only as strong as the teams that create them. By bringing passion, dedication, and creativity to your job every day, there's no telling what you can do and where you can go! We provide a competitive compensation and benefits package, flexible work schedules, opportunities to engage with co-workers, access to career advancement and professional development opportunities, and the chance to make a difference in the communities we serve.

Let's open the door to your career at Teaching Strategies!

Some additional benefits & perks while working with Teaching Strategies

Teaching Strategies offers our employees a robust suite of benefits and other perks which include:

• Competitive compensation package
• Employee Equity Appreciation Program
• Health and wellness insurance benefits
• 401k with employer match
• Flexible work environment 
• Unlimited paid time off (which includes paid holidays and Winter Break)
• Paid parental leave
• Tuition assistance, professional development, and opportunities for career growth
• Best in class technology equipment for every employee
• Penthouse suite in downtown DC seconds away from Washington Nationals Stadium and Audi Field

Teaching Strategies is an equal opportunity employer and is committed to fostering a workplace where everyone can thrive.

Equal Employment Opportunity (EEO) 
Family and Medical Leave Act (FMLA) 
Employee Polygraph Protection Act (EPPA)