Consultant, Payroll Operations

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 em