Pie Insurance · 14 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 focused on empowering small businesses by making commercial insurance affordable and accessible through technology. They are seeking a Director of People Operations and Technology to enhance their HR function using AI and technology, while overseeing the team member lifecycle and aligning with various organizational centers of excellence.
Financial ServicesInsuranceInsurTechSmall and Medium Businesses
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
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; cultivates internal and external networks for identifying emerging opportunities and novel strategies that open new possibilities for their team and function; prepares for scale while identifying inefficiencies that solve functional challenge
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, flexing and adapting as needs and context change; recognizes when behavior/thinking is below the line, and actively works to uplevel self
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; demonstrates emotional control and role models Pie's communication and feedback model; engages in constructive debate while actively listening; seeks and receives real-time candid feedback with kindness and positive intent
Execution: Has high standards for performance and execution that continues to increase as you and the function develop and as the business requires it; willing and able to operate in detail mode, knowing when and how to flex between the strategic birds-eye view and the tactical details and providing direction and guidance to the team; fosters a culture of high accountability within team, leading by example
Team Organization & Planning: Designs organizational structures that address business needs, team effectiveness, and team development and that can scale; develops operational rhythms that ensure functional alignment, develops monitoring systems that reduce complexity and provide real-time visibility into performance and enable risk identification
Team Building & Performance Management: Builds and executes talent strategies to enable the function to achieve and maintain a level of performance; sets and measures against clear expectations at the individual and team level on a monthly, quarterly, and bi-annual basis
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
H1B Sponsorship
Pie Insurance has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2024 (2)
2021 (1)
2020 (1)
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
The Philadelphia Inquirer
2025-08-13
Company data provided by crunchbase