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. The People Operations Generalist is responsible for a variety of employment-related functions within the organization. This role typically includes tasks such as employee relations, performance management, compliance with labor laws, and benefits administration. The People Operations Generalist acts as a point of contact for team members and leaders, providing guidance and support on team member issues. They may also be involved in developing and implementing policies and procedures, conducting training sessions, and ensuring a positive work environment. The position requires strong communication and organizational skills, as well as the ability to handle sensitive information with confidentiality. How You’ll Do It - Navigate Employee Relations and Compliance - Compliance Expertise: - Stay up to date on the latest changes to legislations, locally, state, and federally; especially noting diversity-related policies and regulations - Ensure compliance with labor laws and regulations, maintain employee records, and update People policies. - Notify and advise People Team leaders of employee relations trends and/or compliance issues with laws and regulations. - Employee Relations: - Provide guidance to leaders on employee relations, performance management, and separation decisions, ensuring proper documentation and compliance. - Performance Management: - Assist with performance evaluations, setting goals, and providing feedback. - Data & Reporting Support - Workforce Analytics - Analyze workforce data to identify diversity gaps and trends. - Generate reports and provide insights on People related metrics. - Data Management: - Ensure data hygiene in HRIS and Drive, ensuring best practice for data integrity. - Systems Support & Process: - Support optimal system functionality through active troubleshooting; maintain tenant health. - Advise on best practices and functionality to best utilize tech-stack for People team initiatives and programs. - Support People Operations process improvement efforts through process design updates and testing. - People, Process and Programs Support - Employee Engagement & Programming: - Create initiatives to promote inclusive workplace culture. - Collaborate with leadership to integrate diversity goals into business strategy. - Collaborate with cross-functional teams to provide feedback on key programs (PP > EoYR, Engagement Survey, etc.). - Benefits & Leave Admin: In collaboration with Sr. Total Rewards Manager: - Advise team members on leave options. - Support organization benefit program design and roll-out. - Team Member Lifecycle: - Support onboarding programming to align with business strategy and initiatives. - Manage headcount process ensuring data alignment, accurate job descriptions, and process continuity. The Right Stuff - High school diploma or equivalent experience is required. A Bachelor's Degree is preferred. HR Certification is preferred. - 5 years HR administrative, Rewards, Benefits, or Generalist experience. Experience with enterprise HRIS is a plus. - Applies complete knowledge and full understanding of the principles and practices of Human Resources and People Operations. Uses independent evaluation, judgment, and interpretation to select the right course of action as it relates to employee relations, training, performance management and compliance. - Resolves team member and leader issues in creative ways and suggests alternative courses of action as appropriate. Identifies solutions based on information and precedent, then works collaboratively to resolve issues. Work is done independently and is reviewed at critical points. - Demonstrates curiosity, tenacity, flexibility, and adaptability. Challenges self to eagerly learn from mistakes. Seeks to understand frequently and is open to new information and changes. Adapts to changes. - Written and verbal communication with team members and leaders is direct and empathetic, even when talking about the hard stuff. Understands others by seeing increasing layers of nuance. Expresses self effectively by presenting own views and making requests in a direct and open manner. Fosters open communication and dialog. - Analyzes and solves increasingly complex and nuanced employment related issues by assessing unusual circumstances and identifying the root cause. Builds solutions by applying creativity and challenging the status quo. Relentlessly committed to improvement through learning and creativity. - Builds partnerships with team members and leaders. Demonstrates interpersonal awareness by developing and sustaining collaborative working relationships. Prioritizes the needs of Team Members and leaders to ensure timely response to inquiries. Gains cooperation by achieving team goals and building buy-in for simple proposals. Fosters collaboration by building commitment and trust. - Adept at using HRIS, preferably Workday. Experience using project management software, such as JIRA and various collaboration tools including Google Docs and Slack messaging. Experience or ability to learn People Systems tech-stack for key programs (CultureAmp, Continu, Tilt). - Up to 5% travel may be required for this position. 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 $80,000—$100,000 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 InformationPie 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. Pie Insurance participates in the E-Verify program. Please click here, here and here for more information. Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy. 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. Pie Named to 2025 America's Best Startup Employers Pie Insurance 2025 State of Workplace Safety Report #LI-REMOTE #BI-REMOTE