[Hiring] Director, People Operations & Total Rewards @Pie Insurance

Role Description

Pie is seeking an exceptional Director of People Operations & Total Rewards (Dir, POps & TR) to join the People leadership team. This role will shape and elevate our human resources function at a strategic level through AI, technology, and a blend of business- and people-centered approaches.

The Dir, POps & TR reports to the Chief People Officer (CPO) and serves as a critical member of the People, Talent & Executive Support (PTE) leadership team. Responsibilities include:

• Co-developing and driving people operations, total rewards, and technology strategies.
• Accountability for the team member lifecycle delivery and experience from pre-hire through retire.
• Providing structure, data, and analysis necessary for executing Pie’s people-driven strategies.
• Aligning with and influencing multiple centers of excellence across the organization.

The Dir, POps & TR will own the development and execution of 12+ month strategies that shape functional direction and inform broader people strategy, aligned to company objectives. Key responsibilities include:

• People Operations and tech strategy co-development with the CPO.
• Payroll management.
• Total Rewards strategy and administration.
• Strategic ownership and governance of the People, Talent and Exec Operations technology stack.
• Workday configuration, maintenance, and data integrity.
• People workflow, process design, and SOP management.
• Reporting and analytics.
• Contractor program oversight and reporting, and compliance.

Qualifications

• 12 or more years of progressive experience in People (HR) with 5+ years in people operations, Total Rewards, and tech stack ownership (Workday required).
• 5 or more years of direct people management experience.
• Demonstrated track record of shaping functional strategy and influencing outcomes.
• Prior experience in a high-growth tech-forward environment preferred.
• Workday certification(s) preferred.
• Bachelor’s degree or equivalent experience required.

Requirements

• Deep knowledge of HR workflow, regulatory, and compliance requirements.
• Strong working knowledge of Total Rewards design and administration.
• Outstanding technical and analytical capabilities.
• Capability to plan and execute HR transformation projects.
• Ability to develop, test, and implement tech- and AI-enabled solutions.

Benefits

• Competitive cash compensation.
• Comprehensive health plans.
• Generous PTO.
• Future-focused 401k match.
• Generous parental and caregiver leave.