Director, People Operations and Technology

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.   Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

With approximately 350 team members today, and scaling through people and technology for the future, Pie is seeking an exceptional Director of People Operations and Technology (Dir, POps & Tech) to join the People leadership team. This role will elevate our human resources function through the strategic use of AI, technology, and a blend of business- and people-centered approaches. 

The Dir, POps & Tech reports to the Chief People Officer (CPO). This Director role will serve as a critical member of the People, Talent & Executive Support (PTE) leadership team, working in a highly collaborative environment as a thought and execution partner. The Director of People Operations and Technology is responsible for the ownership of post-hire team member lifecycle delivery and experience, providing the structure, data, and analysis necessary for Pie’s leaders and our People Talent teams to execute against Pie’s people-driven strategies. Given the range of capabilities and responsibilities of the role, this position will also align with multiple centers of excellence across the organization, such as business intelligence, finance, analytics, and culture ambassadorship.

The Dir, POps & Tech will own the development of multi-year strategies that shape team direction, inform functional strategy, and are aligned to company objectives. The Director leads a broad scope of people operations functions including people operations and tech strategy co-development with the CPO and execution through a multi-year roadmap; Tier 1 team member support; payroll management; management of the People and Talent technology stack with a strong focus on Workday configuration, maintenance, and data integrity; People workflow, process design and SOP management; reporting and analytics; and compliance. At the outset, the role is also expected to partner closely with the Dir, Talent to support Talent Operations. Aligning all of these areas around cohesive, strategic narratives that connect to Pie’s market positions and competitive differentiation will be key to our collective success. 

How You’ll Do It

Strategic Leadership, Team Leadership & Cross-Functional Collaboration

• 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

People Operations Management

• 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

Tech Stack Management

• 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 secur