Head of People

The Role

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 - Mondays, Tuesdays, and Thursdays). 

Key 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

About You

Experience:

• 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

You are:

• 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

About Pilot 

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of AI, custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,500 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot? 

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including additional wellness benefits
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is between $165,000 - $210,000 (L5) or $200,000 - $250,000 (L6) in San Francisco, CA. The base pay range target is $130,000 - $165,000 (L5) or $160,000 - $200,000 (L6) in Nashville, Tennessee and most remote locations. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.