Director, People Operations and Technology [Remote]

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 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
• 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

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

The Right Stuff

Experience 

• 12 or more 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 or more years of direct people management experience, including building, developing, and leading teams to consistent achievement of excellent business outcomes

• 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 1,000- 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 financial services 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
• 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

Expected Competencies 

• 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

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. All AI-reviewed applications 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

$160,000—$200,000 USD

Compensation & 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
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges. 

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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Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

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