Associate or Senior Associate Tax Controversy & Litigation Attorney

Orlando Tax Law is seeking an Associate or Senior Associate Tax Attorney to join our growing tax controversy and litigation practice.

We are a boutique law firm devoted exclusively to representing individuals and businesses in disputes with the IRS, Florida Department of Revenue, and other state tax agencies. Our matters include IRS audits and appeals, complex collection cases, penalty disputes, innocent spouse claims, federal tax liens and levies, Trust Fund Recovery Penalty matters, Tax Court litigation, Federal District Court matters, and controversies involving the Florida Department of Revenue and other state taxing authorities.

We are open to two types of exceptional candidates:

• A talented developing attorney with strong tax credentials, intellectual curiosity, excellent judgment, and the drive to become a sophisticated tax controversy practitioner; or
• An experienced tax controversy attorney who can immediately take ownership of complex cases, develop strategy, manage client relationships, and help lead a growing practice.

This is an opportunity to perform meaningful, challenging work without a mandatory 2,100-hour law firm model. The position has a core annual expectation of approximately 1,500 billed hours. Attorneys who want to produce at higher levels can earn substantial additional compensation through the firm’s performance-based bonus structure, which rewards production through 2,100 billed hours.

We value honesty, compassion, accountability, excellent legal work, and sustainable long-term careers.

• Represent individuals and businesses in federal and state tax controversy matters.
• Handle IRS examinations, administrative appeals, collection cases, penalty matters, Tax Court and District Court matters.
• Develop and implement strategic case plans based on the client’s legal, procedural, and financial circumstances.
• Draft correspondence, administrative protests, petitions, motions, briefs, settlement proposals, and other legal filings.
• Communicate and negotiate with IRS Revenue Officers, Revenue Agents, Appeals Officers, IRS Counsel, and state taxing authorities.
• Represent clients before the United States Tax Court and in other litigation matters based on experience and readiness.
• Analyze tax returns, IRS transcripts, financial statements, accounting records, collection financial information, and administrative files.
• Conduct research involving the Internal Revenue Code, Treasury Regulations, federal case law, IRS guidance, and applicable state tax law.
• Maintain organized and proactive case management, including accurate deadlines, task lists, file notes, and clearly documented next steps.
• Communicate clearly and compassionately with clients facing significant financial and legal stress.
• Collaborate with attorneys, paralegals, and administrative professionals.
• Participate in selected consultations with qualified prospective clients based on experience, workload, and firm needs.
• Contribute to the continued development of the firm’s systems, templates, litigation capabilities, and professional standards.

• Active membership in good standing in the Bar of at least one U.S. state or territory. Florida Bar membership is preferred but not required.
• At least one year of legal experience.
• Strong interest in tax controversy, tax litigation, IRS procedure, or complex financial disputes.
• Excellent legal research, analytical, writing, and verbal communication skills.
• Ability to understand tax returns, financial records, IRS transcripts, and accounting information.
• Strong organization, judgment, time management, and follow-through.
• Ability to independently manage deadlines and accept responsibility for assigned matters.
• Commitment to contemporaneous time entry, proactive case management, and measurable professional accountability.
• Ability to earn the trust of clients who are often facing serious financial stress.
• Collaborative, dependable, compassionate, and interested in building a long-term career with the firm.

Preferred Qualifications

The following qualifications are helpful but not required:

• An LL.M. in Taxation.
• Meaningful federal or state tax controversy experience.
• Prior experience with the IRS Office of Chief Counsel, Department of Justice Tax Division, United States Tax Court, a state taxing authority, a sophisticated tax practice, or a national accounting firm.
• Tax Court admission or eligibility and willingness to obtain admission promptly.
• Experience handling complex collection matters, audits, administrative appeals, Trust Fund Recovery Penalty cases, innocent spouse claims, federal tax liens, or tax litigation.
• Five or more years of relevant experience for senior-level consideration.

Exceptional attorneys with fewer years of practice are encouraged to apply if they have strong tax credentials, relevant experience, excellent judgment, and the ability to learn quickly.

Orlando Tax Law is a boutique tax controversy and litigation firm representing individuals and businesses both in central Florida and nationwide in disputes with the IRS, Florida Department of Revenue, and state tax agencies.

Our work is strategic, sophisticated, and frequently high-stakes. We believe clients deserve both excellent legal representation and clear, compassionate communication during what may be one of the most stressful periods of their lives.

We are building a firm where talented attorneys can take meaningful ownership of their cases, develop expertise, be rewarded for strong performance, and build a sustainable long-term career.