Remote Director, People Operations

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