Payroll & Benefits Operations Manager

MatchaCFO is a fractional, AI-enabled COO, CFO, accounting, and data services firm based in Silicon Valley, CA. We deliver modern, full-stack financial and business operations services to US-based digital tech startups. We act as trusted advisors to founders and leverage best-in-class technology and streamlined processes to operate at 'Silicon Valley' speed.

Skills, Experience, Qualifications, If you have the right match for this opportunity, then make sure to apply today.

ROLE

You will own end-to-end payroll and benefits operations across our client engagements, ensuring accuracy, compliance, and a high-quality client experience. You will work closely with Controllers, CFOs, and founders to ensure payroll integrates cleanly into financial reporting and supports broader finance operations.

You will operate both strategically (designing and improving scalable payroll processes) and tactically (running payroll and resolving issues).

This client-facing role requires strong communication, fluency with systems such as Gusto, Rippling, and Justworks, and attention to detail in a fast-paced environment.

This is a remote contractor role with flexible hours (20–40 hours/week), ideal for experienced payroll professionals who value autonomy and flexibility, and want exposure to high-growth tech startups.

RESPONSIBILITIES

Payroll & Benefits Operations

• Manage end-to-end payroll processing across multiple clients and pay cycles (semi-monthly, bi-weekly, off-cycle)
• Administer payroll across platforms, including Gusto, Rippling, Justworks, and TriNet
• Ensure accurate payroll calculations, including wages, bonuses, commissions, equity compensation, and deductions
• Manage employee benefits administration, including enrollments, changes, and reconciliations
• Maintain payroll records and ensure proper documentation across systems

Accounting & Reconciliation

• Prepare and/or review payroll journal entries and ensure accurate posting to the general ledger
• Reconcile payroll clearing accounts, benefits liabilities, and tax accounts in line with Matcha best practices
• Partner with accounting teams to support month-end close and reporting

Compliance & Risk Management

• Ensure compliance with federal, state, and local payroll tax requirements
• Manage payroll tax filings, registrations, and notices across jurisdictions
• Support audits, due diligence, and investor requests related to payroll and benefits
• Monitor regulatory changes and proactively implement updates

Client Service & Advisory

• Serve as a primary point of contact for client payroll-related questions and issues
• Advise clients on payroll setup, multi-state expansion, contractor vs employee classification, and benefits structures
• Support onboarding of new clients, including payroll system setup and process design

Process & Systems Improvement

• Build and document scalable payroll processes across clients
• Identify and implement workflow improvements to increase accuracy and efficiency
• Leverage automation and integrations across payroll, HRIS, and accounting systems
• Attributes
• You take pride in delivering a high-quality client experience with zero-defect expectations
• You are proactive and anticipate issues before they arise
• You are detail-oriented and highly organized, especially across multiple clients and deadlines
• You are systems-oriented and enjoy optimizing workflows
• You are comfortable operating independently in a remote, fast-paced environment
• You communicate clearly and confidently with clients and internal teams
• You demonstrate strong judgment on when to escalate vs resolve independently xhyhwjd

Skills & Qualifications

• 7–10+ years of payroll experience, with significant exposure to US-based digital tech startups
• Deep hands-on experience with Gusto, Rippling, Justworks, and/or TriNet (multi-platform experience strongly preferred)
• Strong understanding of multi-state payroll, payroll taxes, and compliance requirements
• Experience integrating payroll with QBO
• Familiarity with benefits administration and related accounting implications
• Proficient with Google Workspace (Docs, Sheets) and Slack
• Strong analytical and problem-solving skills with high attention to detail
• Proven ability to manage multiple clients and deadlines simultaneously
• Experience building and documenting repeatable processes
• Bachelor's degree in accounting, finance, or related field preferred
• Certified Payroll Professional (CPP) or similar credential is a plus (not required)

Technical Requirements

• High-performance computer (Mac or equivalent PC, 16GB RAM minimum)
• Reliable high-speed internet (100 Mbps download / 25 Mbps upload minimum)
• At least one external monitor (27"+ recommended)
• Ability to operate efficiently across cloud-based tools and 100+ browser tabs