Transactional Attorney

Flanagan - Bilton LLC; Chicago, Northern (IL, KY); Hybrid; USD 72,000 - 88,000; Full time

Benefits offered by this job

PTO after probation (120 hours)

Paid holidays (17+)

Employer-provided health/dental/vision

Employer 401k with 3% match after one

Business casual dress code

Team atmosphere

Annual reviews

Job summary

Flanagan - Bilton LLC is seeking a highly skilled Transactional Attorney for our national real estate tax practice. You will architect complex deals, structure tax-efficient transactions, and lead negotiations and closings across jurisdictions.

The role requires 3–6+ years of sophisticated transactional real estate experience, JD, and strong knowledge of tax codes. Expect a high-impact, fast-paced environment with cross-functional collaboration.

Qualifications

• JD from ABA-approved law school.
• Active member in good standing of state bar.
• 3–6+ years of sophisticated transactional real estate experience.
• Strong working knowledge of federal and state tax codes as they apply to real property.

Responsibilities

• Deal structuring & advisory for tax‑efficient acquisitions, dispositions, and joint ventures.
• Draft and negotiate PSAs, leases, loan documents, and partnership agreements.
• Lead tax-focused due diligence to identify liabilities and environmental risks.
• Identify and secure real estate tax incentives (e.g., NMTC, LIHTC, 1031 exchanges).
• Oversee closing process, ensure compliance, funds transfer, and recording nationwide.
• Ensure transactions comply with federal, state, and local laws.

Skills

Negotiation

Analytical rigor

Written & verbal communication

Transaction management

Education

Juris Doctor (JD)

LL.M. in Taxation

CPA certification

Job description

Job Summary

We are seeking a highly skilled and strategic Transactional Attorney to join our national real estate tax practice. The ideal candidate will serve as a "deal architect," navigating the complex intersection of commercial real estate and sophisticated tax law. You will be responsible for structuring, negotiating, and closing high-stakes transactions while ensuring tax efficiency and regulatory compliance across multiple jurisdictions.

Core Responsibilities

Deal Structuring & Advisory: Provide strategic counsel on tax-efficient deal structures for acquisitions, dispositions, and joint ventures.

Document Drafting & Negotiation

Draft and negotiate a wide range of complex agreements, including Purchase and Sale Agreements (PSAs), commercial leases, loan documents, and partnership agreements.

Tax-Focused Due Diligence

Lead the due diligence process, with a specific focus on identifying tax liabilities, reviewing title and survey materials, and assessing environmental risks.

Tax Incentive Optimization

Collaborate with specialists to identify and secure real estate tax incentives, such as 1031 exchanges, New Markets Tax Credits (NMTC), or Low-Income Housing Tax Credits (LIHTC).

Closing Management

Oversee the entire closing process, ensuring all legal requirements are met, funds are correctly transferred, and deeds are properly recorded nationwide.

Compliance & Risk Management

Ensure all transactions comply with federal, state, and local property and tax laws.

Required Qualifications

Education

Juris Doctor (JD) from an ABA-approved law school.

Licensure

Active member in good standing of at least one State Bar.

Experience: 3-6+ years of sophisticated transactional real estate experience, ideally within a large or national law firm environment.

Tax Expertise

Strong working knowledge of federal and state tax codes as they apply to real property.

Preferred Qualifications

• LL.M. in Taxation or a CPA certification.
• Experience with specialized financing (e.g., NMTC, CDFI lending, or affordable housing).

Essential Skills

• Exceptional negotiation skills with a focus on balancing client interests and deal viability.
• Strong analytical rigor and attention to detail for reviewing complex financial and legal documents.
• Excellent written and verbal communication for advising high-net-worth clients and institutional investors.
• Ability to manage multiple large-scale transactions simultaneously in a fast-paced environment.

Compensation

• Starting Salary: 80,000
• 120 hours of PTO after a 90-day probation period
• Typically, 17 plus paid holidays
• Employee-only medical, dental, vision, and basic life premium insurance paid by the employer
• 3% of salary, employer 401k contribution after one year of employment
• Business casual dress code with exceptions based on assigned tasks and positions
• Team atmosphere
• Annual reviews

The above is intended to describe the general content of and requirements for the performance of this job. It is not to be construed as an exhaustive statement of all essential functions, responsibilities, or requirements.

A pre-employment background check is required.