Director, People Operations & Total Rewards
Pie Insurance · Remote · United States · $190k–$230k
Posted by Pie Insurance on their careers site · View the original posting
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The posting, as Pie Insurance wrote it
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 & Total Rewards (Dir, POps & TR) to join the People leadership team. This role will shape and elevate our human resources function at a strategic level through AI, technology, and a blend of business- and people-centered approaches.
The Dir, POps & TR reports to the Chief People Officer (CPO). This Director role serves as a critical member of the People, Talent & Executive Support (PTE) leadership team, partnering directly with the CPO to co-develop and drive people operations, total rewards and technology strategies. The Director is accountable for the team member lifecycle delivery and experience from pre-hire through retire and supporting the alumnae experience. With this broad-reaching responsibility, the Director provides the structure, data, and analysis necessary for Pie’s leaders and People, Talent and Executive Operations teams to execute against Pie’s people-driven strategies. Given the breadth of responsibilities, this position will align with and influence multiple centers of excellence across the organization — including business intelligence, finance, analytics, and culture ambassadorship.
The Dir, POps & TR will own the development and execution of 12+ month strategies that shape functional direction and inform broader people strategy, aligned to company objectives. This role has three core pillars of ownership: People Operations, Total Rewards, and PTE Technology. Within these pillars, the Director is responsible for: people operations and tech strategy co-development with the CPO; payroll management; Total Rewards strategy and administration, including compensation, benefits, equity and leave programs — with a Total Rewards expert executing under their leadership; strategic ownership and governance of the People, Talent and Exec Operations technology stack with a strong focus on AI and automation; Workday configuration, maintenance, and data integrity; People workflow, process design and SOP management; reporting and analytics; contractor program oversight and reporting, and compliance. The role is also expected to partner closely with the Dir, Talent to support Talent Operations and the Manager of EA team to support Executive Operations. Aligning all of these areas around cohesive strategies that connect to Pie’s goals and competitive differentiation will be key to our collective success.
The right person for this role is restless about improvement — not just executi
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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
$190,000 — $230,000 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 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.