Director, People Operations & Total Rewards

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 & Total Rewards (Dir, POps & TR) to join the People leadership team. This role will shape and elevate our human resources function at a strategic level through AI, technology, and a blend of business- and people-centered approaches.

The Dir, POps & TR reports to the Chief People Officer (CPO). This Director role serves as a critical member of the People, Talent & Executive Support (PTE) leadership team, partnering directly with the CPO to co-develop and drive people operations, total rewards and technology strategies. The Director is accountable for the team member lifecycle delivery and experience from pre-hire through retire and supporting the alumnae experience. With this broad-reaching responsibility, the Director provides the structure, data, and analysis necessary for Pie’s leaders and People, Talent and Executive Operations teams to execute against Pie’s people-driven strategies. Given the breadth of responsibilities, this position will align with and influence multiple centers of excellence across the organization — including business intelligence, finance, analytics, and culture ambassadorship.

The Dir, POps & TR will own the development and execution of 12+ month strategies that shape functional direction and inform broader people strategy, aligned to company objectives. This role has three core pillars of ownership: People Operations, Total Rewards, and PTE Technology. Within these pillars, the Director is responsible for: people operations and tech strategy co-development with the CPO; payroll management; Total Rewards strategy and administration, including compensation, benefits, equity and leave programs — with a Total Rewards expert executing under their leadership; strategic ownership and governance of the People, Talent and Exec Operations technology stack with a strong focus on AI and automation; Workday configuration, maintenance, and data integrity; People workflow, process design and SOP management; reporting and analytics; contractor program oversight and reporting, and compliance. The role is also expected to partner closely with the Dir, Talent to support Talent Operations and the Manager of EA team to support Executive Operations. Aligning all of these areas around cohesive strategies that connect to Pie’s goals and competitive differentiation will be key to our collective success.

The right person for this role is restless about improvement — not just executing the function, but continuously evolving it. They bring fresh eyes and a bias for experimentation to People Operations, and as a natural side effect of how they operate, they will contribute to making adjacent People team functions better as well. This cross-functional lift isn’t their core responsibility, but it is a hallmark of the leader we’re looking for.

How You’ll Do It

Strategic Leadership, Team Leadership & Cross-Functional Collaboration

Design and sustain an innovative, effective, and inclusive work culture that retains and grows the best talent for the People Team and Pie as an organization

Directly manage the People and Talent Operations team, currently comprised of four full-time team members with varying levels of experience and responsibility and which is expected to grow as the business demands

Continuously improve the People Operations function — not just maintaining what exists, but actively evolving how the team operates, identifying what’s not working, and leading the team to a better state over time

Bring fresh perspective and a partnership mindset to adjacent People team functions; while not directly responsible for those areas, contribute actively to their improvement through shared ideas, candid feedback, and collaborative experimentation

Continuously uplevel thought leadership specific to People Operations and Total Rewards, leveraging emerging frameworks, AI, and technologies to shape how the function operates

Accountable for all aspects of people management across the team, including development, coaching, training, and performance management

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

Serve as the strategic owner of Total Rewards at Pie, setting direction on compensation philosophy, benefits strategy, and equity administration; partner with the Total Rewards expert on execution and with Finance and Legal on governance

Partner proactively with People Partners, 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 (CDMF), serve in a lead execution role, as well as supporting and consultative roles, on cross-functional, complex project and program management initiatives

Lead across the organization as an AI champion and expert, freely sharing learnings and adaptable approaches with leaders and teams across the organization

People Operations Management

Lead the People Operations team through strategic processes, projects, and complex situations; set the organizational standard for rigor, execution, and continuous improvement

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 oversee the People tech stack and resources (Culture Amp, Continu, Ethena, Carta (shared), etc.) while driving AI solutions for faster and higher quality outcomes

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

Project & Program Management

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

Establish and maintain 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

Data Integrity, Management & Analysis

Monitor, audit, maintain, and troubleshoot the HRIS system to ensure data integrity and system compliance

Maintain data integrity by developing routine audit procedures, cre