Remote Senior People Partner - Contract

Independent Contractor | 1099 | Remote About the Engagement 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. Pie is seeking an experienced Senior People Partner on an independent contractor basis to serve as a trusted advisor to business leaders and drive people strategies that enable leaders and their teams to achieve high-impact goals. This is a contract (1099) engagement. The contractor will operate independently, bringing their own tools, methods, and professional judgment to bear on defined deliverables and project scopes. The engagement structure — hourly, project-based, or retainer — will be defined in the Statement of Work. The Senior People Partner contractor will work closely with the Chief People Officer and People flag risk areas for internal review and resolution. Support management and documentation of common-to-moderately complex team member relations issues under the direction of the CPO. Talent Development support delivery of targeted training or enablement initiatives as scoped. Provide advisory support on performance management processes, helping leaders drive development, engagement, and results. Use data and available tools to develop recommendations that empower leaders in performance management, team culture, and engagement. Team Member Experience Sales, Marketing, or Business Development; Engineering, Product Development, or Technology. Proficient in Workday and collaboration tools (Slack, Google Suite). Experience with Greenhouse and Culture Amp preferred. Knowledge of incentive plan design is a plus. Expected Competencies Ownership: Takes full accountability for contracted deliverables. Operates independently with a solutions-first mindset. Follows through on commitments, flags blockers proactively, and drives resolution within scope. Critical Thinking: Uses sound judgment and data to assess situations and develop practical, actionable recommendations. Applies integrative thinking to navigate complexity across multiple stakeholders and competing priorities. Growth Mindset: Demonstrates curiosity and flexibility. Adapts approach when circumstances change, integrates feedback, and brings continuous improvement thinking to every engagement. Collaboration commits fully once aligned. Strategy: Develops scoped people strategies (typically 6–12 month horizon) aligned with defined business objectives. Connects deliverables to broader functional priorities and surfaces risks proactively. Communication: Communicates clearly and directly in writing and verbally with managers, directors, and People team stakeholders. Adapts style to the audience. Navigates sensitive conversations with directness and care. Minimizes ambiguity in all stakeholder communications. Execution: Delivers high-quality outputs within defined scope, timeline, and budget. Takes end-to-end ownership of contracted work, identifies obstacles early, and resolves them without hand-holding. Engagement