Head of People

Pilot.com•Nashville, TN

19h•$130,000 - $250,000•Hybrid

About The Position

At Pilot, we’re building the modern back office for startups, and our people are at the center of everything we do. As Head of People, you will define and scale the people strategy that enables Pilot to attract, develop, and retain exceptional talent while maintaining a high performance, collaborative culture. You’ll serve as a strategic partner to the executive team and a hands-on operator who can build systems from scratch, improve what exists, and guide the company through its next phase of growth. This role requires both thoughtful leadership and a willingness to roll up your sleeves, balancing long-term vision with day-to-day execution. This role reports to the Chief Administrative Officer. Location: San Francisco, CA or Nashville, TN (3 days/week in office). Exceptional candidates will be considered for a remote position.

Requirements

10+ years of experience in HR/People Operations at one or more growth companies, supporting a geographically distributed workforce
Experience scaling People functions in high-growth, startup or tech-enabled environments
Expertise across all general areas of HR, including people operations, employee relations, performance management, compensation and benefits, and employee experience
High level of autonomy and sound judgment
Approachable and able to build strong relationships with leaders across the company
Strategic thinker who can also execute on tactical necessities. No task is too large or too small
An exceptional communicator with the ability to influence across all levels of the organization
Data-driven and systems-oriented, able to bring structure to ambiguity
A trusted partner who exercises sound judgment and maintains high integrity
Energized by building teams, developing leaders, and shaping company culture
Comfortable operating in a fast-moving environment

Responsibilities

Oversee and scale People Operations and programs
Oversee and strengthen all core People Ops functions, including onboarding, offboarding, HRIS, policies, and compliance
Manage and develop a high performing People team across People Ops, Facilities, and Recruiting
Build and maintain scalable, efficient processes that support a growing, distributed team
Own compliance across all federal, state, and local employment laws, including maintaining accurate documentation and ensuring timely, accurate reporting
Lead and execute performance review cycles, compensation processes, and benefits programs with a high level of accuracy and consistency
Identify opportunities to simplify and improve People processes and programs as the company scales
Lead employee relations and enable managers
Serve as the strategic point of contact for employee relations matters, including performance issues, conflict resolution, and investigations
Partner with managers to provide clear and consistent guidance while coaching through performance, feedback, difficult conversations, and team health
Proactively identify and mitigate organizational risk through thoughtful policies and interventions
Build simple, effective frameworks and guidance that help managers lead with clarity and consistency
Drive employee experience and engagement
Own and continuously improve onboarding, engagement, and retention programs
Lead response to employee feedback to drive the evolution of the employee experience, improving metrics such as eNPS, employee satisfaction, productivity, and/or retention
Ensure employees have clarity on policies, expectations, and available resources
Oversee recruiting
Oversee the recruiting function, ensuring effective processes, a strong talent bar, and a consistent candidate experience
Partner with hiring managers and recruiters to drive high-quality hiring decisions aligned with company needs
Identify gaps in hiring processes and implement improvements as the company scales
Step in to support recruiting efforts as needed during periods of high growth or critical hires