Pie Insurance · 8 hours ago
Director, People Operations and Technology
United States
Full-time
Remote
Lead/Staff, Director/Executive
$160K/yr - $200K/yr
12+ years expPie Insurance is committed to empowering small businesses by transforming how they experience commercial insurance. They are seeking a Director of People Operations and Technology to elevate their HR function through strategic use of technology and innovative practices, while managing the People Operations team and overseeing the HRIS and tech stack.
Financial ServicesInsuranceInsurTechSmall and Medium Businesses
No H1B
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
Qualification
Required
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 of developing, testing, and implementing tech- and AI-enabled solutions that create a flywheel of continuous improvement for the team and company, both independently and with stakeholders
Demonstrated capability to plan and execute HR transformation and/or system implementation projects leveraging agile and iterative methodologies
Has the knowledge, and cultivates the relationships, necessary to provide thoughtful insights on market trends, best practices, and benchmarking
Preferred
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
Pie Insurance
Pie Insurance is an insurance company specializing in small business.
201-500 employees
Funding
Current Stage
Late StageTotal Funding
$621MKey Investors
Gallatin Point CapitalSVB CapitalGreycroft
2022-09-21Series D· $315M
2021-03-25Series C· $118M
2020-05-28Series B· $127M
Leadership Team
John Swigart
Co-Founder and CEO
Audra Foglietta
Chief Financial Officer
Recent News
Hartford Business Journal
2025-08-14
Company data provided by crunchbase