Tax Professional | Niche CPA Career

This is a niche, specialized role at the intersection of tax preparation and the growing professional gambling/sports betting industry — a market that has expanded significantly since PASPA's repeal in 2018. Building expertise in gambling taxation is a genuinely differentiated skill set with limited competition.

Compensation signals: No salary is published, which is a mild red flag for transparency. For a tax professional with 3+ years of experience and CPA credentials, market rates typically range from $60,000–$100,000+ annually depending on volume and complexity. The quarterly discretionary bonus structure adds upside but also uncertainty.

Green flags:

• No business development required — clients are assigned, so you can focus purely on technical work
• Full return ownership (intake through e-filing) builds deep, end-to-end experience
• Multi-state filing expertise is a high-demand, transferable skill
• Small, focused company suggests direct impact and minimal bureaucracy

Potential considerations:

• Niche client base (professional gamblers) may limit resume transferability to traditional CPA firms
• No mention of team size, growth trajectory, or advancement path
• Seasonal nature of tax work means workload may be highly uneven throughout the year

Overall, this role suits an experienced tax preparer or CPA who wants remote flexibility, enjoys autonomous work, and is interested in a distinctive niche within tax services. It's a strong fit for someone building a specialized practice rather than climbing a corporate ladder.

Little Wheel develops software for professional gamblers, including automated bet tracking, portfolio management, and tax reporting tools.

We're seeking an experienced tax professional to prepare individual federal, state, and local income tax returns for professional gamblers using our platform.

Clients are assigned by Little Wheel, so there is no sales or business development – you'll own each return from intake through filing, working independently within a fully remote team.

Responsibilities

• Manage each return end to end: intake, document collection and review, preparation, client follow-up, authorizations, and e-filing
• Accurately report income, deductions, and credits, including gambling-related income
• Identify multi-state filing requirements and prepare state and local returns
• Handle tax notices, amended and prior-year returns, and tax research
• Explain filing requirements, liabilities, and refunds clearly to clients
• Keep accurate, confidential records and meet all filing deadlines
• Stay current on federal, state, and local tax rules

Required Qualifications

• Active PTIN
• Active EFIN, or willingness to obtain one with Little Wheel's support
• 3+ years preparing, reviewing, and signing individual income tax returns

Preferred Qualifications

• Active CPA license

Compensation and Benefits

• Quarterly discretionary bonuses
• Monthly reimbursement for health insurance premiums (QSEHRA)
• Home office equipment allowance

Little Wheel is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other legally protected characteristic.

Is this tax professional position fully remote? Yes, Little Wheel operates as a fully remote team. You will work independently with no in-office requirement. Do I need to find my own clients in this role? No. Clients are assigned to you by Little Wheel, so there is no sales or business development involved — you focus entirely on preparing and filing returns.

What credentials are required to apply? You must have an active PTIN and either an active EFIN or willingness to obtain one with Little Wheel's support. A CPA license is preferred but not strictly required. What does the compensation package include? The role includes quarterly discretionary bonuses, monthly reimbursement of health insurance premiums via a QSEHRA plan, and a home office equipment allowance.

A specific base salary is not publicly stated. Do I need prior experience with gambling-related taxes? Prior gambling tax experience is not explicitly listed as a requirement, but you will be handling gambling related income, deductions, and multi-state filings for professional gambler clients, so familiarity is beneficial.