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 & Talent team, supporting business leaders (primarily Managers and Directors) across assigned functional areas. Scope, deliverables, and engagement duration will be outlined in the applicable Statement of Work.

Scope of Work
The contractor may be engaged to support any combination of the following, as defined in the Statement of Work:

Strategic Business Partnership

Translate defined business priorities into actionable people strategies that support culture, team performance, and business outcomes within assigned client groups.

Partner with managers and directors to assess current-state people needs and provide recommendations on organizational design, talent management, and performance development.

Analyze trends and metrics to identify gaps and develop targeted solutions, programs, or policy recommendations for People team review.

Change Management

Support planning and execution of organizational changes, including team restructures, leadership transitions, and People & Talent program rollouts.

Develop change communication plans and adoption support materials for defined initiatives within assigned client groups.

Employee Relations & Compliance Consultation

Advise on team member relations matters including performance management, conflict resolution, and employee development — in coordination with the internal People team.

Provide guidance on employment law considerations and HR best practices; 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 & Performance Enablement

Partner with leaders to identify skill gaps and recommend development approaches; 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 & Engagement

Support execution of team member engagement strategies in coordination with the People team.

Help leaders interpret engagement data and develop action plans to address identified themes and opportunities.

Provide targeted recommendations for retention within critical roles in assigned client groups.

Systems & Reporting Support

Utilize Pie’s HR systems (Workday, Greenhouse, Culture Amp, Google Suite, Slack) as needed to complete scoped deliverables.

Leverage data and reporting to support program delivery and provide analysis within the defined scope of work.

The Right Fit
Experience

12+ years of HR experience, related business industry experience, or leading teams with HR-related functions, or a combination of related experience/education.

6+ years of experience in an HR Business Partner or People Partner role or equivalent, supporting managers and directors.

Demonstrated experience operating as an independent contractor or consultant in an HR/People Partner capacity preferred.

Prior experience supporting one or more of the following: Insurance Underwriting, Claims, Customer Service/Support or Operations; 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 & Influence: Builds credible, trust-based relationships quickly with internal leaders and People team partners. Prioritizes solutions that serve organizational goals. Disagrees directly when warranted; 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 & Compensation

This is an hourly independent contractor (1099) engagement. Rate, estimated hours, timeline, and deliverables will be defined in a mutually executed Statement of Work. This engagement does not include employee benefits, equity, paid time off, or other employment-related compensation. The contractor is responsible for their own taxes, insurance, and business expenses unless otherwise specified in the Statement of Work.

Location

This is a fully remote engagement. Contractors must be based in and legally authorized to work in the United States. Reliable high-speed internet access is required.

Additional Information

Pie Insurance is an equal opportunity company. 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 in our contracting relationships.

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