Director, People Operations

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

📋 Description

• Take full ownership of Headway's benefits strategy from inception to execution, encompassing funding model evaluation and the implementation of an updated strategy.

• Revamp employee assistance for leave, career, and claims concerns, as well as benefits inquiries and immigration matters.

• Guarantee precise and timely payroll processing that adheres to compliance across all states where Headway operates.

• Spearhead a comprehensive revision of employee policies and enhance employee record management.

• Establish the strategic direction for People Systems, with a focus on Workday.

• Collaborate with Human Intelligence and People Analytics to develop self-service capabilities that empower employees.

• Redesign the lifecycle operations for contingent workers, including onboarding, offboarding, extensions, and conversions, utilizing automated and AI-driven workflows.

• Foster change adoption through training, documentation, and resource enablement.

• Assess reductions in manual tasks, escalations, and the overall impact of workflows over time.

• Mentor and grow a high-performing team of Managers and Associates.

• Work closely with Finance and Legal departments.

• Report directly to the Director of Total Rewards and Operations.

⛳️ Requirements

• Over 10 years of experience in People Operations or Total Rewards.

• At least 5 years of experience in managing and developing a high-performing team.

• Proficient in reconstructing People workflows and support systems on automated frameworks.

• Demonstrated experience in minimizing significant manual effort, lowering error rates, or enhancing SLAs through automation.

• Proficient with modern data and automation tools.

• Knowledge of AI within the infrastructure layer of People programs.

• Capable of converting ambiguous business requirements into a structured roadmap.

• Strong communication skills across various audiences.

• Experience managing workflows and data for a large employee base and adapting to rapid scaling.

• Proven success in managing intricate, cross-functional projects involving diverse stakeholders.

• Familiarity with HR technology platforms such as Workday and Ashby, including integration and API capabilities, is a plus.

• Must possess authorization to work in the United States.

🏝️ Benefits

• Equity and substantial ownership opportunities.

• Comprehensive health and wellness benefits.

• Retirement savings plans.

• Flexible remote work arrangements.

• Reasonable accommodations for individuals with disabilities.