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, 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

Total Rewards Strategy & Administration

• Own Total Rewards strategy at Pie, including compensation philosophy, benefits design, and equity administration; ensure the Total Rewards program is competitive, compliant, and aligned to Pie’s mission and stage
• Lead the Total Rewards expert in day-to-day execution of compensation, benefits, and equity programs; serve as escalation point and strategic guide
• Partner with Finance on compensation modeling, headcount planning, and total rewards budgeting
• Manage external compensation and benefits vendors, consultants, invoices, and contracts
• Manage payroll contributions and 401(k) match processes
• Manage all total rewards-related reporting and maintain accuracy of compensation and benefits data
• Maintain systems to ensure accuracy of compensation data, job profiles, bonus targets, equity, and more
• Stay current on market benchmarking and compensation trends; translate insights into recommendations for Pie’s leadership

The Right Stuff

Experience

• 12 or more years of progressive experience in People (HR) with 5+ years of experience across people operations, Total Rewards (compensation, benefits, and/or equity), and tech stack ownership (Workday required); experience in Tier 1 team member relations, payroll management, and regulatory and compliance management also required
• 5 or more years of direct people management experience, including building, developing, and leading teams to consistent achievement of excellent business outcomes
• Demonstrated track record of shaping functional strategy and influencing outcomes in partnership with senior and C-level stakeholders
• Prior experience preferred in a high-growth tech-forward environment with a mix of private and public company experience preferred
• You know what great looks like in a 400 to 5,000-person company and can also thrive in an earlier-stage environment that requires flexibility and building tools and resources, sometimes from scratch
• Prior experience in insurance, insurtech, fintech, healthtech, lending, or tech preferred
• Workday certification(s) preferred
• Bachelor’s degree or equivalent experience required

Knowledge & Capabilities

• 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
• Strong working knowledge of Total Rewards design and administration — including compensation structures, benefits programs, and equity plans — with the ability to translate market data and business needs into competitive, sustainable programs
• 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
• Outstanding technical and analytical capabilities with specific experience in People (HR), Talent and organizational technology, metrics, reporting, and data visualization
• Has the knowledge, and cultivates the relationships, necessary to provide thoughtful insights on market trends, best practices, and benchmarking — and to translate those insights into functional strategy

Expected Competencies

• Ownership: Demonstrates extreme ownership and a one-team mindset — We Are The They — modeling this across the function and with cross-functional leadership partners
• Collaboration & Influence: Builds high-trust relationships across the organization; works collaboratively with cross-functional stakeholders to identify and consider a wide range of needs, designing solutions that solve for the most needs at functional scale
• Critical Thinking: Leverages first principles, integrative thinking, and Pie’s CDMF to design data-driven, maximum win/win solutions that consider all stakeholder needs
• Strategy: Develops 12+ month functional strategies and aligns teams and cross-functional partners around cohesive strategic narratives; cultivates internal and external networks for identifying emerging opportunities; identifies systemic inefficiencies and drives toward better outcomes
• Growth Mindset: Leads with questions and curiosity; demonstrates self-awareness and humility; models continuous learning and growth through integration of personal, team, and cross-functional feedback; recognizes when behavior or thinking is below the line and actively works to uplevel self and the team
• Grit & Resilience: Persists through complex challenges while role modeling resiliency and supporting team members and peers across the function
• 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: Sets and maintains high standards for performance and execution that grow with the function and the business; flexes between strategic birds-eye view and tactical operational detail; fosters a culture of high accountability across the team and function, leading by example
• Team Organization & Planning: Designs organizational structures that address business needs and team effectiveness; develops operational rhythms that ensure functional and cross-functional alignment; builds monitoring systems that reduce complexity and provide real-time visibility into performance while enabling risk identification
• Team Building & Performance Management: Builds and executes talent strategies to enable the function to achieve and maintain a high level of performance; sets and measures against clear expectations at the individual and team level on a monthly, quarterly, and bi-annual basis

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range

$190,000—$230,000 USD

Compensation & Benefits 

• Competitive cash compensation
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information 

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

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