[Remote] Director, People Operations and Technology

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 https://pieinsurance.com.