Director, People Operations & Total Rewards

Pie Insurance

2d • $190,000 - $230,000 • Remote

About The Position

Pie Insurance is seeking a Director of People Operations & Total Rewards to shape and elevate its human resources function through strategic, business- and people-centered approaches, technology, and AI. The position reports to the Chief People Officer and is a member of the People, Talent & Executive Support leadership team. The Director partners with the CPO to develop and drive people operations, total rewards, and technology strategies, and is accountable for team member lifecycle delivery and experience from pre-hire through retirement, as well as the alumnae experience.

The role owns the development and execution of strategies spanning more than 12 months across three pillars: People Operations, Total Rewards, and PTE Technology. Responsibilities include payroll management; total rewards strategy and administration covering compensation, benefits, equity, and leave programs; governance and strategic ownership of the People, Talent and Executive Operations technology stack; Workday configuration, maintenance, and data integrity; workflow and process design; SOP management; reporting and analytics; contractor program oversight and reporting; and compliance. The Director partners with the Director of Talent on Talent Operations and the Manager of the EA team on Executive Operations, and works with functions including business intelligence, finance, analytics, and culture.

The Director directly manages the People and Talent Operations team, currently four full-time team members, and is accountable for coaching, development, training, and performance management. The position is expected to continuously improve how People Operations works, lead cross-functional initiatives, and champion AI and technology-enabled improvements. It owns the Workday HRIS and broader People technology stack, systems administration and releases, reporting and data governance, vendor relationships, and the People Operations and Technology budget. The Director also sets Total Rewards direction, leads a Total Rewards expert in program execution, and partners with Finance and Legal on governance and planning.

The role is remote. Remote employees must live and work in the United States, excluding territories, and have reliable, high-speed internet. The base compensation range is $190,000–$230,000 USD. Pie offers competitive cash compensation, comprehensive health plans, generous PTO, a 401(k) match, generous parental and caregiver leave, and discretionary bonuses that may be granted to eligible team members based on annual company performance.

Requirements

• 12 or more years of progressive People/HR experience.
• At least 5 years of experience across People Operations, Total Rewards (compensation, benefits, and/or equity), and technology stack ownership; Workday experience is required.
• Experience in Tier 1 team member relations, payroll management, and regulatory and compliance management.
• At least 5 years of direct people management experience, including building, developing, and leading teams to strong business outcomes.
• Demonstrated track record of shaping functional strategy and influencing outcomes with senior and C-level stakeholders.
• Bachelor’s degree or equivalent experience.
• Deep knowledge of HR workflow, regulatory, and compliance requirements across the employee lifecycle, with ability to develop efficient, compliant workflows, processes, and SOPs.
• Strong working knowledge of Total Rewards design and administration, including compensation structures, benefits programs, and equity plans, and ability to translate market data and business needs into sustainable programs.
• Ability to develop, test, and implement technology- and AI-enabled solutions independently and with stakeholders.
• Ability to plan and execute HR transformation and/or system implementation projects using agile and iterative methods.
• Strong technical and analytical capabilities, including experience with People/HR, Talent, and organizational technology, metrics, reporting, and data visualization.
• Knowledge of market trends, best practices, and benchmarking, and ability to translate insights into functional strategy.
• Ability to communicate clearly and confidently with audiences at all company levels, including the CEO and Senior Leadership Team.
• Ability to develop functional strategies extending 12 or more months and align teams and cross-functional partners around them.
• Ability to lead through complex challenges, adapt between strategic and operational work, and maintain high standards for accountability and execution.

Nice To Haves

• Prior experience in a high-growth, technology-forward environment.
• Experience in both private and public companies.
• Experience in a 400- to 5,000-person company and ability to thrive in an earlier-stage environment that requires flexibility and building tools and resources.
• Experience in insurance, insurtech, fintech, healthtech, lending, or technology.
• Workday certification(s).

Responsibilities

• Design and sustain an innovative, effective, and inclusive work culture that retains and grows talent for the People Team and Pie.
• Directly manage the People and Talent Operations team, including team development, coaching, training, and performance management.
• Continuously improve and evolve the People Operations function, identifying ineffective practices and leading improvements.
• Contribute ideas, candid feedback, and collaborative experimentation to improve adjacent People team functions.
• Advance People Operations and Total Rewards thought leadership using emerging frameworks, AI, and technology.
• Build strong working relationships with Finance & Accounting, Enterprise Technology, Internal Communications, Legal & Compliance, Product, the Executive Team, Senior Leadership Team, and the Office of the CEO.
• Own Pie’s Total Rewards strategy, including compensation philosophy, benefits strategy, and equity administration, in partnership with the Total Rewards expert, Finance, and Legal.
• Partner with People Partners, Talent, Executive Support, and Space teams on strategy and execution across People, Talent & Executive Support.
• Lead or support complex cross-functional project and program management initiatives using Pie’s Collaboration and Decision Making Framework.
• Champion AI across the organization and share learnings and adaptable approaches with leaders and teams.
• Lead the People Operations team through strategic processes, projects, and complex situations, setting standards for rigor, execution, and continuous improvement.
• Design, deliver, and monitor the People Operations strategic roadmap on monthly, quarterly, and annual bases.
• Oversee approval of biweekly payroll for exempt and non-exempt team members.
• Own the strategic design, delivery, and administration of Workday and oversee the People technology stack, including Culture Amp, Continu, Ethena, and shared Carta resources; drive AI solutions.
• Manage the People Operations and Technology budget and People-specific vendor and service-provider relationships.
• Administer Workday security, including user and role-based security groups.
• Own configuration, testing, deployment updates, process improvements, and business process updates across HCM, Compensation, Advanced Compensation, Benefits, Time Tracking, Absence, US Payroll, and Talent.
• Manage the biannual Workday release cycle and administer integrations, troubleshooting enhancements, issues, errors, and vendor requests.
• Partner with PTE and organization-wide stakeholders to identify and prioritize system development needs and align configuration goals with PTE priorities.
• Plan and execute moderate to complex projects with cross-functional subject matter experts.
• Oversee Tier 1 team member support provided by the People Operations team.
• Establish and maintain documentation for processes, workflows, system configuration, and integrations, and train the team in best practices for People systems.
• Monitor, audit, maintain, and troubleshoot the HRIS to ensure data integrity and system compliance.
• Develop routine audit procedures and reports, analyze data, and define corrective solutions; establish data management standards for entry, integration, validation, and quality assurance.
• Respond to systems support and reporting requests; build custom reports and dashboards, fulfill ad hoc requests, and analyze complex datasets.
• Ensure People Systems comply with internal technology, procurement, and retention policies.
• Own Total Rewards strategy, ensuring programs are competitive, compliant, and aligned to Pie’s mission and stage.
• Lead the Total Rewards expert’s day-to-day execution of compensation, benefits, and equity programs, serving as an escalation point and strategic guide.
• Partner with Finance on compensation modeling, headcount planning, and total rewards budgeting.
• Manage external compensation and benefits vendors, consultants, invoices, and contracts.
• Manage payroll contributions and 401(k) match processes.
• Manage Total Rewards reporting and maintain accurate compensation and benefits data, including job profiles, bonus targets, and equity.
• Monitor market benchmarking and compensation trends and translate findings into recommendations for Pie’s leadership.
• Lead, execute, contribute to, or consult on projects, programs, and other work as needed.

Benefits

• Competitive cash compensation.
• Comprehensive health plans.
• Generous PTO.
• Future-focused 401(k) match.
• Generous parental and caregiver leave.
• Eligible team members may receive discretionary bonuses based on annual company performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Director