Founding Startup Tax Lead, EA or CPA

Overview

A Series A startup in the tax technology sector is seeking a Founding Startup Tax Lead who is an Enrolled Agent (EA) or CPA. This remote position is open to candidates located in the USA only. The role reports directly to the CEO and partners closely with Engineering, Product, and Leadership teams. The salary range is $150,000 to $200,000 annually, depending on expertise, plus equity.

Responsibilities

• Act as the primary tax subject matter expert, bridging traditional tax compliance with AI-enabled tax strategy.
• Translate complex Internal Revenue Code (IRC) rules and tax strategies into clear rules, workflows, and review standards for AI learning.
• Codify high-value tax strategies such as the Augusta Rule, Accountable Plans, Section 179, and R&D credits into operational frameworks for product and engineering teams.
• Build and manage the tax fulfillment organization, including the human-in-the-loop review process and standard operating procedures (SOPs) to ensure efficiency and consistency.
• Own quality assurance and compliance standards, ensuring all returns meet Circular 230 expectations and internal quality gates.
• Analyze feedback loops where human reviewers correct AI outputs and update guidance and rules to prevent recurring issues.
• Drive efficiency improvements by reducing manual oversight while maintaining accuracy.
• Serve as a strategic advisor for early customers (approximately 50–100), validating recommendations and shaping the service experience.
• Initially perform hands-on review and filing for clients with extensions; subsequently focus on architecting, strategizing, and building the team and processes.
• Build and lead a team of CPAs over time.

Qualifications

• Minimum 4 years of senior-level SMB tax experience as an Enrolled Agent, including expertise with S-Corps (1120-S), Partnerships (1065), and high-net-worth individual returns (1040).
• Experience with tax strategies including Augusta Rule, Accountable Plans, Health Savings Accounts, Health Reimbursement Arrangements, 529 Accounts, Hiring Your Kids, Traditional and ROTH IRAs, and SOLO 401(k)s.
• At least 2 years of people management experience (2 to 4 years preferred).
• Strong working knowledge of the IRC and practical application of tax strategy.
• Proficiency with tax practice management software, tax preparation software, and integration tools.
• Experience collaborating with senior leadership and engineering teams.
• Demonstrated ability to lead teams and build repeatable processes such as SOPs, quality checks, and review workflows.
• Comfortable working in a fast-paced startup environment balancing speed and compliance risk.
• Tech-forward mindset with motivation to scale quality through automation and systems.
• Strong judgment and ability to clearly communicate tax logic to non-tax stakeholders.
• Experience with hiring practices.

Preferred Qualifications

• Active CPA license.
• Experience building or leading teams of Enrollment Agents or CPAs.
• Background in TaxTech or leading change within traditional tax firms.
• Experience managing review "pods" or high-throughput tax operations.
• Familiarity with AI-enabled tax tools, automation, or process improvement initiatives.
• Hands-on experience with TaxDome, ProConnect, and Juno software.
• Prior experience working in early-stage startups.
• Comfortable participating in client strategy calls and representing tax strategy.
• Willingness to relocate to the Jacksonville, FL area in time for Tax Season 2027 to work a hybrid schedule (3 days per week in office).

Compensation & Benefits

• Salary range: $150,000 to $200,000 annually, based on expertise.
• Equity participation.

Location

• Remote within the USA initially.
• Expected to transition to a hybrid role based in the Jacksonville, FL metro area by Tax Season 2027, working approximately three days per week in the office.