Transactional Attorney
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Flanagan - Bilton LLC
Chicago, IL, US
Summary
The Transactional Attorney will serve as a deal architect, structuring and negotiating complex real estate transactions while ensuring tax efficiency. They will also lead due diligence processes and oversee the closing of high-stakes deals across multiple jurisdictions.
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.
Flanagan | Bilton LLC is a firm of experienced attorneys, CPA's, appraisers and tax consultants who have represented clients on property tax matters for over 50 years. Unlike tax consulting firms, we provide services that offer tax consulting opinions as well as expert legal advice in matters strictly related to property taxes. Prior to entering private practice, our founding partners accumulated 25 years of state and local government service – focusing on tax matters, property valuations and litigation at both the trial and appellate level.
Based in Chicago, our exceptional national practice serves more than 1,000 clients in all 50 states, including a wide-range of real estate investment trusts (REIT’s), banks, insurance companies and pension funds.
Founded
1967
Company size
51-200 employees
Industry
Law Practice
Org type
Partnership
Headquarters
Chicago, Illinois
Flanagan | Bilton LLC is a firm of experienced attorneys, CPA's, appraisers and tax consultants who have represented clients on property tax matters for over 50 years. Unlike tax consulting firms, we provide services that offer tax consulting opinions as well as expert legal advice in matters strictly related to property taxes. Prior to entering private practice, our founding partners accumulated 25 years of state and local government service – focusing on tax matters, property valuations and litigation at both the trial and appellate level.
Based in Chicago, our exceptional national practice serves more than 1,000 clients in all 50 states, including a wide-range of real estate investment trusts (REIT’s), banks, insurance companies and pension funds.
Founded
1967
Company size
51-200 employees
Industry
Law Practice
Org type
Partnership
Headquarters
Chicago, Illinois