Senior Payroll Specialist

The Role
Pilot's Financial Operations team helps startup founders and business owners manage critical people operations across payroll, benefits, and HR administration for a portfolio of growing businesses.
We are hiring a Consultant, Payroll Operations to provide hands-on payroll and HR operations support to that portfolio. This Consultant owns recurring payroll processing, payroll and HRIS implementations and provider transitions, benefits administration, employee onboarding/offboarding, and multi-state payroll tax registration and compliance - working directly with clients to keep payroll accurate, on time, and scalable as teams grow.
Key Responsibilities

• Own the payroll cycle end to end: Manage recurring payroll for a portfolio of clients - coordinating inputs (new hires, terminations, comp changes, bonuses, commissions, reimbursements, deductions), leading implementations and provider transitions (requirements, configuration, data migration, parallel testing, reconciliation), and managing multi-state tax registrations, notices, and compliance to resolution.
• Administer benefits and HR operations: Set up and run employee benefit programs (health, dental, vision, 401(k)); coordinate with brokers, retirement providers, and payroll platforms on implementations, renewals, and open enrollment; and own onboarding, offboarding, and employee changes across HRIS and payroll systems.
• Be the client's operational partner: Serve as a knowledgeable point of contact across payroll, benefits, and HR; translate client needs into accurate, scalable processes; communicate clearly on issues and next steps; maintain documentation; and identify opportunities to improve workflows, controls, and the client experience - including standardized processes and implementation playbooks.
  

About You

• Experience: 2-4 years in payroll administration, payroll operations, HR operations, benefits administration, or a related field.
• Hands-on payroll expertise: Processed and managed payroll start to finish, with working knowledge of federal, state, and local payroll tax — including multi-state registrations, compliance, and navigating employees across jurisdictions.
• Systems and implementations fluency: Experience implementing or supporting payroll and HRIS platforms (Rippling, Gusto, ADP, Paychex, or similar) and transitioning companies between providers.
• Benefits and people operations range: Comfortable administering benefits (health insurance, 401(k)s) and managing onboarding/offboarding, deductions, employer contributions, and employee data across systems.
• Detail-oriented and self-directed: Manages multiple clients, payroll calendars, and deadlines with accuracy; strong problem-solving and research instincts; works independently and knows when to escalate high-risk issues.
• Clear communicator: Explains complex issues and next steps clearly to clients, and brings integrity and discretion to sensitive employee, payroll, and benefits data.
  

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 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 3,000 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 wellness benefits such as Spring Health, Headscape, One Medical, Aaptiv and Rightway
• 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 $65,600 - $88,800 in Nashville. 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.