Job Description
Note: The job is a remote job and is open to candidates in USA. Pie Insurance is committed to empowering small businesses by making commercial insurance affordable and accessible. They are seeking a Director of People Operations and Technology to enhance their HR function through strategic use of technology and people-centered approaches, overseeing the team member lifecycle and collaborating across various departments. Responsibilities • Ensure an innovative, effective, and inclusive work culture to retain and grow the best talent for the People Team and Pie as an organization • Directly manage the People Operations team, currently comprised of three full-time team members with varying levels of experience and responsibility • Responsible for all aspects of people management, including development, coaching, training, performance management, and the expected future growth of the team • Lead and develop new People team leaders in order to build bench strength as the business grows over time • Proactively establish and maintain strong collaborative working relationships across the organization with a focus on the following stakeholders: Finance & Accounting, Enterprise Technology, Internal Communications, Legal & Compliance, Product, the Pie Executive Team, the Senior Leadership Team, and the Office of the CEO • Proactively partner with People Partners, Total Rewards, Talent, and the Executive Support and Space teams on strategy development and outstanding execution across all aspects of the People, Talent & Exec Support functions • Leveraging Pie’s Collaboration and Decision Making Framework, you will often serve in a lead execution role, as well as in supporting and consultative roles on cross-functional, complex project and program management initiatives • Lead the People Operations team through strategic processes, projects, and complex situations • Design, deliver, and monitor the strategic roadmap for the People Operations function on a monthly, quarterly, and annual basis • Oversee payroll approval for the biweekly pay cycle for non-exempt and exempt team members • Own the strategic design, delivery, and administration of our HRIS (Workday) and have oversight for the People tech stack and resources (Culture Amp, Continu, Ethena, Carta (shared), etc.) • Manage the People Operations and Technology budget as well as People-specific vendor relationships and service providers • Serve as the security admin for Workday, managing user and role-based security groups • Own configuration, testing, and deployment updates, process improvements, and business process updates in HCM, Compensation, Advanced Compensation, Benefits, Time Tracking, Absence, US Payroll, and Talent • Manage the bi-annual Workday release cycle • Serve as the integration administrator to troubleshoot integration enhancements, issues, errors, or vendor requests • Partner across the PTE team and key stakeholders organization-wide to identify and prioritize system development needs • Align system configuration goals with PTE goals to optimize the HRIS' value • Plan and execute moderate to complex projects, partnering with cross-functional SMEs • Oversee Tier 1 team member support provided by the People Operations team • Develop capabilities to provide Tier 2+ support for end-users, inclusive of the People Partnering team and Tier 2 team member relations • Continuously uplevel thought leadership specific to People Operations and Technology, leveraging emerging frameworks and technologies • Keep our house clean through comprehensive documentation of process, workflow, system configuration, and integration • Establish and train the team using best practice methods for People systems • Lead, execute, contribute to and/or consult on projects, programs and work as needed • Monitor, audit, maintain, and troubleshoot the HRIS system to ensure data integrity and system compliance • Maintain data integrity by developing routine audit procedures, creating audit reports, analyzing data, and defining corrective solutions • Respond to requests for systems support and reports • Develop data management protocols and standards, including data entry, integration, validation, and quality assurance procedures • Establish and document audit procedures for the People Systems tech stack • Ensure People Systems align with internal technology, procurement, and retention policies • Build custom reports and dashboards for key metrics; fulfill ad-hoc report requests • Analyze complex datasets to ensure system functionality and set-up Skills • 12+ years of progressive experience in People (HR) with specific experience in people operations and tech stack ownership (Workday required), tier 1 team member relations, team member resource development and delivery, payroll management, and regulatory and compliance management • 5 + years of direct people management experience, including building, developing, and leading teams to consistent achievement of excellent business outcomes • Bachelor's degree or equivalent experience required • Deep knowledge of HR workflow, regulatory, and compliance requirements across the employee lifecycle, with the capability to develop rigorous, highly efficient, compliant workflows, processes, and standard operating procedures • Outstanding technical and analytical capabilities with specific experience in People (HR), Talent and organizational technology, metrics, reporting, and data visualization • Demonstrated capability to plan and execute HR transformation and/or system implementation projects leveraging agile and iterative methodologies • Ownership: Leads with a one-team, extreme ownership mindset, We Are The They • Collaboration & Influence: Develops high-trust relationships org-wide and works collaboratively with cross-functional stakeholders to identify and consider a wide range of needs, creatively designing solutions that solve for the most needs • Critical Thinking: Leverages first principles, integrative thinking, and Pie's Collaboration and Decision-Making Framework (CDMF) for designing the data-driven, maximum win/win solutions, considering all stakeholder needs • Strategy: Demonstrates the ability to think integratively as an organizational leader, develops multi-year strategies and aligns multiple functions around cohesive strategic narratives • Growth Mindset: Leads with questions and curiosity, demonstrating self-awareness and humility, models continuous learning and growth through integration of personal, team, and cross-functional feedback • Grit & Resilience: Persists through complex challenges while role modeling resiliency and supporting the team and peers • Communication: Writes and speaks with accuracy, clarity and confidence with audiences at all levels of the company, including the CEO and Senior Leadership Team • Execution: Has high standards for performance and execution that continues to increase as you and the function develop and as the business requires it • Team Organization & Planning: Designs organizational structures that address business needs, team effectiveness, and team development and that can scale • Team Building & Performance Management: Builds and executes talent strategies to enable the function to achieve and maintain a level of performance • Prior experience preferred in a high-growth tech-forward environment with a mix of private and public company experience preferred • Prior experience in insurance, insurtech, fintech, healthtech, lending, or financial services preferred • Workday certification(s) preferred Benefits • Competitive cash compensation • A piece of the pie (in the form of equity) • Comprehensive health plans • Generous PTO • Future focused 401k match • Generous parental and caregiver leave Company Overview • Pie Insurance is an insurance company specializing in small business. It was founded in 2017, and is headquartered in Washington, District of Columbia, USA, with a workforce of 201-500 employees. Its website is