Director, People Operations – Total Rewards

This is a fully remote position, open to applicants in United States.

📋 Description

• Transform and enhance Pie’s human resources function utilizing AI, technology, and business- and people-focused strategies.

• Report directly to the Chief People Officer and be a part of the People, Talent & Executive Support leadership team.

• Collaborate in the development and implementation of people operations, Total Rewards, and technology strategies.

• Oversee the entire team member lifecycle experience from pre-hire to retirement, which includes managing the alumnae experience.

• Create and implement functional strategies for over 12 months that align with the company’s objectives.

• Lead the pillars of People Operations, Total Rewards, and PTE Technology.

• Supervise payroll, compensation, benefits, equity, leave programs, Workday, People workflows, reporting, analytics, contractor oversight, and compliance.

• Directly manage and nurture the People and Talent Operations team.

• Establish the strategic roadmap for People Operations and oversee biweekly payroll approvals.

• Take ownership of the Workday HRIS and the broader People technology stack, including aspects such as configuration, security, integrations, testing, releases, and data integrity.

• Manage the budgets for People Operations and Technology along with vendor relationships.

• Plan and execute moderately complex to complex cross-functional projects and programs.

• Develop documentation, audit procedures, data protocols, reports, dashboards, and corrective measures.

• Lead the Total Rewards strategy, compensation philosophy, benefits design, and equity administration.

• Collaborate with Finance, Legal, People Partners, Talent, Executive Support, and other organizational stakeholders.

• Advocate for AI adoption and continuous improvement throughout the organization.

⛳️ Requirements

• A minimum of 12 years of progressive experience in People (HR).

• Over 5 years of experience in people operations, Total Rewards, and ownership of technology stacks.

• Required experience with Workday.

• Experience in Tier 1 team member relations, payroll management, and regulatory and compliance management is necessary.

• At least 5 years of direct experience in people management.

• Proven history of shaping functional strategies and influencing senior and C-level stakeholders.

• Previous experience in a high-growth, tech-focused environment is preferred.

• Background in insurance, insurtech, fintech, healthtech, lending, or technology is preferred.

• Workday certification(s) are preferred.

• A Bachelor’s degree or equivalent experience is required.

• Extensive knowledge of HR workflows, regulatory, and compliance requirements across the employee lifecycle.

• Strong understanding of Total Rewards design and administration, including compensation, benefits, and equity plans.

• Ability to develop, test, and implement technology- and AI-enabled solutions.

• Capable of planning and executing HR transformation and/or system implementation projects using agile and iterative methodologies.

• Possess technical and analytical skills in HR, Talent, and organizational technology, including metrics, reporting, and data visualization.

• Remote team members must reside and work within the United States, excluding territories.

• Must have access to reliable, high-speed internet.

• Ability to provide work authorization documentation as part of E-Verify participation.

🏝️ Benefits

• Competitive cash compensation.

• Comprehensive health plans.

• Generous PTO.

• Future-focused 401k match.

• Generous parental and caregiver leave.

• Discretionary bonuses may be awarded annually to eligible team members.

• Reliable, high-speed internet access is required for remote work.