M&A and Transactional Attorney (Mid-Level)

Tomlinson & Shapiro, P.C.
Chicago, IL

Firm Description

Tomlinson & Shapiro, P.C.is a dynamic business law firm built for sophisticated clients who value practical advice, responsiveness, and strategic thinking. We serve as trusted counsel to established companies, closely held businesses, and entrepreneurs by acting as fractional general counsel, leading mergers and acquisitions, advising on capital raises, and guiding clients through complex transactions.


Our firm is intentionally structured to deliver high‑quality work without the bureaucracy, inefficiency, or burn‑out culture common at larger firms. We prioritize excellent client service, thoughtful legal work, and long‑term professional growth.


The Opportunity

We are looking for a high-performing M&A and Transactional attorney to join our growing practice on a full-time basis. This role is ideal for an attorney who is ready to operate with meaningful responsibility, work closely with clients, and build a long‑term career in a firm that rewards initiative and excellence.


This role offers a hybrid work environment, allowing for both in-office collaboration and flexibility for remote work, as well as a competitive compensation structure commensurate with experience. We offer a clear path for professional advancement, leadership, and optional business development over time.


What You Will Do

In this role, you will be a key contributor on sophisticated transactions and a trusted advisor to business clients, including:

  • Leading and managing mergers and acquisitions, capital raises, and other complex business transactions
  • Serving as fractional/outside general counsel, advising clients on day‑to‑day legal and strategic business matters
  • Drafting, reviewing, and negotiating a wide range of commercial contracts and transactional documents
  • Leading entity formation, restructuring, and governance matters
  • Identifying and interpreting existing and evolving laws and regulations to help clients make informed, risk‑aware decisions
  • Working directly with partners and clients in a hands‑on, collaborative environment


You will have real ownership over your work, direct client interaction, and the ability to shape matters from start to finish.


What We’re Looking For

The ideal candidate is motivated, detail‑oriented, and committed to delivering excellent legal work and client service. Qualifications include:

  • JD from an accredited, nationally recognized law school
  • Active State Bar membership
  • 4-7 years of transactional experience, including meaningful exposure to:

- Mergers and acquisitions

- Capital raises

- Business formation and structuring

- Contract drafting, review, and negotiation

  • Experience advising a range of clients, from emerging businesses to large, sophisticated organizations
  • Strong judgment, communication skills, and a proactive mindset
  • Experience with entity taxation is a plus, but not required


Compensation & Benefits

We offer a highly competitive compensation and benefits package designed for long‑term success, including:

  • Competitive salary structure commensurate with experience
  • Paid health coverage for the employee (medical, dental, and vision)
  • Generous PTO, including vacation and sick time
  • 401(k) retirement plan
  • Significantly lower minimum billing requirements than many comparable firms
  • A collegial, supportive environment that values quality over volume


Why Tomlinson & Shapiro

This is not a churn‑and‑burn role. We are building something intentionally—an excellent firm for excellent lawyers who want meaningful work, strong client relationships, and a sustainable career. If you are motivated, client‑focused, and ready to take the next step in your practice, we want to hear from you.


For immediate consideration, please apply directly to this posting. Only those candidates who are invited for interviews will be contacted. All others, we sincerely appreciate your application and time in responding. 

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