At Pie Insurance, our mission is simple: make small business insurance affordable and as easy as pie. We specialize in workers' compensation and commercial auto insurance for small businesses across the U.S. 

With our data-driven approach, small businesses can get a workers’ comp quote in just three minutes and save up to 30% on premiums.* 

At Pie, culture isn’t just a buzzword; it’s what drives us. We’re obsessed with giving our customers the best experience, always curious, and never afraid to tackle challenges head-on. We believe that diversity fuels innovation and we aim to foster an inclusive environment where everyone has an opportunity for impact and growth.

🏆 Pie has been named to: Forbes’ America’s Best Startup Employers 2025, Purpose Jobs’ Best Places To Work Remote in 2025, BuiltIn's Best Places to Work in Colorado (2025), Best Remote Midsize Places to Work (2025), among others. 

⚠️ Safety First ⚠️ 
Pie is committed to your security during the recruitment process. Verify the identity of recruiters before sharing personal or financial details. Protect yourself from job scams and report suspicious activity.

* Individual savings and quote time may vary. Discounts and savings not available for workers’ compensation policies in Wisconsin.


Pie Insurance

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.

At Pie, our “employees” are team members, and we call ourselves Pie-oneers. The Principal People Partner ensures the successful contribution of our Pie-oneers by driving people and organizational strategies that enable and empower our leaders to lead their teams to achieve their highest-impact goals and drive success across the business.

As Pie’s People team evolves, we are seeking a highly strategic yet execution-focused Principal People Partners to serve as a trusted advisor to senior leaders, driving people and organizational strategies that enable our leaders and teams to achieve their highest-impact goals and drive business success. These highly collaborative roles partner with executive leadership to design and implement talent strategies, foster high-performing teams, and build a culture of performance, agility and integrative thinking.

The Principal People Partner role reports directly to the Chief People Officer and works cross-functionally across the PTE team and senior managers (primarily Director+), including the CEO and Pie’s Senior Leadership Team (SLT). As a senior level individual contributor, the Principal People Partner brings considerable leadership influence and is responsible for aligning people strategy with business objectives, leading change management, and providing expert consultation on all aspects of the team member lifecycle.

How You’ll Do It

Strategic Business Partnership

Lead senior management in translating business strategy into a talent strategy that embeds and reinforces our culture and drives success across our businessAlign people strategies with business objectives, partnering with leaders to understand their goals and provide guidance on organizational design and development, all aspects of talent management, workforce planning and management, performance development, total rewards, and experience and benchmarking across the team member lifecycle. Serve as a strategic consultant to leaders, analyzing trends and metrics to identify gaps and patterns and develop solutions, programs, and policies that drive the best business outcomes. 

Change Management

Lead and support organizational change initiatives, including org design, leadership transitions, reporting structure changes, and People & Talent programs.Guide leaders and teams through periods of transformation, developing comprehensive change management and communication plans in order to maximize change adoption and minimize risk and negative impact to the business and organization.

Service, Compliance and Risk Mitigation

Advise people leaders on matters related to team member relations, performance management, and conflict resolution. Identify, manage, and mitigate risk through deep knowledge of employment laws, regulations, and best practices.Maintain in-depth knowledge of legal requirements related to day-to-day and strategic management of team members, reducing legal risks and ensuring regulatory compliance.Manage and resolve common-to-complex team member relations issues. Lead and support team member relations investigations.Support and develop, as the subject matter expert, organizational policy changes and collaborate on cascading communication strategies.

Talent Development & Performance Enablement

Partner with leaders to build and sustain high-performing, outcome-oriented teams where success is recognized and valued.Identify opportunities to enhance knowledge and develop skills; collaborate with enablement resources to create and implement training programs.Oversee the performance management process, ensuring it drives development, engagement, and results.Leverage data, tools, and resources to empower leaders in performance management, team culture, and engagement.

Team Member Experience & Engagement

Collaborate with People Team partners and help to develop and execute team member engagement strategies using systems, tools, and resources.Partner with leaders and People Partners to interpret engagement data and recommend action plans.Develop and execute targeted retention initiatives for critical team member groups.Build relationships with Executive leaders ensuring communication cascades across and down the organization.Support with Executive and Senior leadership onboarding and offboarding experiences. 

Systems, Tools And Experience Management

Demonstrate proficiency in HR systems (Workday, Greenhouse, Culture Amp, Google Suite, Slack), serving as a resource for configuration, user support, and effective adoption.Leverage technology to enhance program delivery, data analysis, and reporting.

The Right Stuff

Thrives in ambiguous, fast-paced, highly dynamic virtual environments requiring a thoughtful balance between autonomy and a high collaboration. 12+ years of progressive HR experience, related business industry experience, or leading teams with HR-related functions, or a combination of related experience/education.8+ years in an HR Business Partner/People Partner role or equivalent partnering with multiple executives.High school diploma or equivalent required; Bachelor’s degree is preferred.Prior experience supporting one or more of the following functional areas:Insurance Underwriting, Claims, Customer Service / Support and/or OperationsSales, Marketing and/or Business Development inclusive of knowledge of incentive plan designEngineering, Product Development, TechnologyMust be proficient with HRIS (Workday preferred) and collaboration tools (Slack, Google Suite)Experience with Greenhouse and Culture Amp preferred.
Expected Competencies 

Ownership: Leads with a one-team, extreme ownership mindset, We Are The They

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, impacts and interdependencies . Can pull self up to see forest from the trees.

Growth Mindset: Models growth mindset and accurate self assessment while remaining genuinely open to feedback. Demonstrates humility by learning from diverse sources, creating a culture where admitting gaps and mistakes is productive and safe. Develops resilience strategies for self and work and others within their sphere of influence. Demonstrates grit by persevering through obstacles. Demonstrates flexibility by proactively changing approaches when strategies and tactics aren’t working and adapts readily to changing circumstances.

Collaboration & Influence: Creates needs-based solutions across team boundaries that serve organizational/functional interests first, consistently putting broader org/function needs ahead of team or personal interests. Builds high candor, high trust, high context relationships across all boundaries within the organization, maximizing operational effectiveness, even with competing priorities and resource constraints. Addresses systemic causes of conflict while effectively resolving disagreements. Lead with first team commitment to the function balanced with service to the organization.

Strategy: Develops 6-month to multi-year strategies integrated with functional and organizational objectives. Creates clear strategic narratives that connect their work to functional priorities. Deeply understands operations within their functional domain and understands operations within their business domain. Recognizes how market and industry shifts impact medium term strategy, both functionally and within the business.

Communication: Writes and speaks with accuracy, clarity and influence with audiences within and outside of functional area at all levels, including the CEO, and across different formats and channels. Creates clear and highly compelling narratives that influence strategy. Communicates directly and respectfully and actively minimizing triangulation and gossip. Makes thoughtful requests solving for intersection of stakeholder needs, avoiding demands and building alignment across competing priorities. Functions as a stabilizing influence during high-stakes situations. Maintains composure and clarity in the most challenging organizational challenges and stress.

Execution: Manages multiple initiatives delivering high impact results, acting as force multiplier through effective delegation, empowerment, and building infrastructure to support scale. Drives operational frameworks to improve efficiency and effectiveness. Identifies opportunities for improving performance and consistently overcomes significant obstacles. Takes ownership of complex challenges beyond immediate scope, demonstrating broader functional and organizational thinking.

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

$150,000 - $185,000 USD

Compensation & Benefits

Competitive cash compensationComprehensive health plansGenerous PTOFuture focused 401k matchGenerous parental and caregiver leaveOur 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.

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

#BI-REMOTE



Principal People PartnerNew United States

What the job involves