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Director, People Operations – Total Rewards

🔥 0 minutes ago

🇺🇸 United States – Remote

💵 $190k - $230k / year

⏰ Full Time

🔴 Lead

👥 People Operations

Where this job comes from

Posted on Pie Insurance's careers page, not through a job board

First seen by Remote Rocketship 0 minutes ago

Logo of Pie Insurance

Pie Insurance

201 - 500 employees

🛡️ Insurance

💳 Fintech

🤝 B2B

Insurance • Fintech • B2B

Pie Insurance is transforming small business insurance by making it less expensive, simpler, and more transparent for small business owners. With a team of seasoned technology and insurance experts, Pie Insurance is dedicated to enhancing the insurance experience, particularly focused on workers' compensation and InsureTech innovations.

📋 Description

• Shape and elevate Pie’s human resources function through AI, technology, and business- and people-centered approaches • Report to the Chief People Officer and serve on the People, Talent & Executive Support leadership team • Co-develop and drive people operations, Total Rewards, and technology strategies • Own team member lifecycle delivery and experience from pre-hire through retirement, including alumnae experience • Develop and execute 12+ month functional strategies aligned with company objectives • Lead People Operations, Total Rewards, and PTE Technology pillars • Manage payroll, compensation, benefits, equity, leave programs, Workday, People workflows, reporting, analytics, contractor oversight, and compliance • Directly manage and develop the People and Talent Operations team • Set the People Operations strategic roadmap and oversee biweekly payroll approval • Own the Workday HRIS and broader People technology stack, including configuration, security, integrations, testing, releases, and data integrity • Manage People Operations and Technology budgets and vendor relationships • Plan and execute moderate to complex cross-functional projects and programs • Establish documentation, audit procedures, data protocols, reports, dashboards, and corrective solutions • Own Total Rewards strategy, compensation philosophy, benefits design, and equity administration • Partner with Finance, Legal, People Partners, Talent, Executive Support, and other organizational stakeholders • Champion AI adoption and continuous improvement across the organization

🎯 Requirements

• 12 or more years of progressive experience in People (HR) • 5+ years of experience across people operations, Total Rewards, and tech stack ownership • Workday experience required • Experience in Tier 1 team member relations, payroll management, and regulatory and compliance management required • 5 or more years of direct people management experience • Demonstrated track record shaping functional strategy and influencing senior and C-level stakeholders • Prior experience in a high-growth tech-forward environment preferred • Prior experience in insurance, insurtech, fintech, healthtech, lending, or tech preferred • Workday certification(s) preferred • Bachelor’s degree or equivalent experience required • Deep knowledge of HR workflow, regulatory, and compliance requirements across the employee lifecycle • Strong working knowledge of Total Rewards design and administration, including compensation, benefits, and equity plans • Capability developing, testing, and implementing technology- and AI-enabled solutions • Capability planning and executing HR transformation and/or system implementation projects using agile and iterative methodologies • Technical and analytical capabilities in HR, Talent and organizational technology, metrics, reporting, and data visualization • Remote team members must live and work in the United States, territories excluded • 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 granted annually to eligible team members • Access to reliable, high-speed internet required for remote work

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