Head of Tax Operations | AI-native accounting firm

Overview

This role is for a licensed CPA who will provide final tax return sign-off on IRS filings prepared using an AI-enabled workflow. The organization supports owner-operated businesses nationwide, including short-term rentals, campgrounds, and hotels, with bookkeeping, tax, and fractional CFO services.

AI is used to prepare returns (including 1040, 1065, 1120S, and C corp returns). Each return requires a licensed CPA’s signature before it is sent to the IRS. You will review AI-prepared outputs, determine whether they should be signed, sent back, or held, and help define the review rules and quality assurance checks used by the workflow.

Responsibilities

• Provide return sign-off under your own license.
• Review AI-prepared returns (1040, 1065, 1120S, and C corp) and decide whether each is:
  • signed and sent,
  • returned for correction, or
  • held for additional review.
• Focus review efforts on areas where software commonly slips:
  • K-1 pass-throughs,
  • basis tracking,
  • multi-state allocations.
• Trace figures back to the source documents the AI engine used.
• Define and document review rules and QA steps with the founder and engineering team, including:
  • edge-case rules,
  • AI error checks,
  • decision points for “hard stops” vs “judgment calls.”
• Determine which returns can receive a lighter review and which require a full read.
• Provide detailed feedback to product/engineering by logging each engine error by:
  • form,
  • line,
  • cause,
  • and including an example an engineer can reproduce.
• Help determine whether errors originate from document scanning, prompt/input choices, or schedule logic, and validate fixes alongside engineering.
• Ensure the organization’s work meets applicable compliance requirements, including IRS regulations, state guidelines, and Circular 230.
• Identify legal tax-optimization strategies for clients and document the reasoning.
• Help build and mentor a lean team of fractional or full-time reviewers using your review playbook.

Requirements

• Active US CPA license.
• Valid PTIN.
• Clean disciplinary record.
• 5+ years preparing and reviewing complex individual and small-business returns, including:
  • 1040s with multiple K-1s,
  • S corps,
  • partnerships,
  • C corps,
  • multi-state clients.
• Final sign-off experience on returns you signed under your own license or last reviewed with no partner behind you, including a reason for each item you held back.
• Experience with tax software and hands-on use of automation, OCR, or AI tools on real client work, with the ability to explain when outputs cannot be trusted.
• Ability to write clear, actionable written instructions for others (e.g., checklists, review rules, or error reports) that junior reviewers or engineers can follow without additional questioning.
• Evidence of building and running your own process or team, such as:
  • a solo practice,
  • early experience at a tech-enabled firm,
  • or running a review process through a full filing season at real volume.

Preferred Qualifications

• Handling IRS or state notices for small-business clients.
• Training or reviewing junior, offshore, or fractional preparers.
• Building prompts or automations for tax or accounting work.
• Reporting recurring errors to a product team in a tax software, fintech, or tech-enabled firm.
• Writing tax-planning memos for S corp owners (reasonable compensation, entity choice).

Compensation & Benefits

• US-based, remote or hybrid.
• Full-time role with founding equity.
• No billable-hour tracking; work is measured on output, leverage, and accuracy.
• Real authority and ownership of final tax review and sign-off.

Location

US-based. Remote or hybrid options available.

Recruitment Process

• Screening call (30 minutes).
• Profile review by the founder.
• Interviews with the founder on the work in the role.
• Offer.