Head of People, Pilot
$165-250k
+ Equity
More information about location
3+ days a week in office
Bookkeeping services for startups
Be an early applicant
Bookkeeping services for startups
201-500 employees
Be an early applicant
$165-250k
+ Equity
More information about location
3+ days a week in office
201-500 employees
Company mission
To help small businesses and startups to achieve their commercial goals by taking care of the CFO services, tax preparation and bookkeeping.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
- 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 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
Our take
Back office operations such as bookkeeping can be an unwelcome distraction and expense for businesses. Pilot is the largest provider of back office services for startups and small businesses in the US, aiming to take care of a company's back office so they can focus on their core activities.
Founded in 2016. Pilot has attracted an impressive range of customers including Bolt, r2c and Pathrise. The company's proposition is more than just bookkeeping software, providing services that would ordinarily be provided by a fractional CFO. This empowers small businesses and startups to make better budgeting and spending decisions without the need of an expensive finance department hire.
The company evidently excels in customer service, with the vast majority of its business driven by customer referrals and organic interest. Going forward, Pilot aims to become to startups and medium-sized firms what AWS is to cloud computing - a comprehensive, easily scalable solution that prevents the need to reinvent a necessary but non-core function from scratch.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2021
$40m
SERIES C
Jan 2021
$60m
SERIES C
Total funding: $158.3m
Company benefits
- Development opportunities & employee happiness initiatives
- 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
- Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
- Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
- 401(k) plan
Company HQ
Financial District, San Francisco, CA
Leadership
Waseem Daher
(Chair & Co-Founder)They studied at MIT before founding Ksplice, where they spent 3 years as COO, and working at Oracle and Dropbox. Having founded Zulip in August 2012, they co-founded Pilot in January 2017.
Jessica McKellar
(CEO & Co-Founder)Previously, they were the founder and the VP of Engineering for a real-time collaboration startup acquired by Dropbox, where they then served as a Director of Engineering.
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