Michele Kalczynski

Michele Kalczynski is an experienced attorney who helps businesses navigate complex commercial and technology transactions with confidence. Prior to joining Outsource Counsel, Michele was a commercial transactions attorney at an Am Law 200 firm where she represented clients in a wide range of transactional matters. In this role, Michele acted as an architect for complex business deals and guided clients, including Fortune 500 companies, through the intricate legal framework. She specialized in drafting, reviewing and negotiating legal documents and providing legal advice on issues that arise throughout the transaction, helping her clients protect their interests and minimize risk.

Michele next went to a consulting firm where she directed the handling of complex, high-exposure litigation on behalf of insurance organizations. She transitioned from litigation management to business consulting where she developed operational, financial and risk management strategies to optimize clients’ performance, drive growth and reduce risk.

Today at Outsource Counsel, Michele leverages her background in law, business consulting and risk management to structure, negotiate and draft commercial and technology agreements. With a sharp eye for risk and a practical, business-minded approach, she partners with clients to develop deal strategies that protect their interests and keep their businesses moving forward in the fast-paced tech sector.

Michele Kalczynski, At A Glance

Bar Admissions

• State Bar of Michigan

Education

• University of Michigan, B.A. in Economics
• Wayne State University School of Law, J.D.

Professional Experience

• Outsource Counsel, PLLC, Attorney (2025-present)
• Sedgwick, Vice President Pool Administration (2012-2024)
• York Risk, Director of Program Management (2010-2012)
• American Risk Pooling Consultants, Litigation Management Attorney (2004-2010)
• Dickinson Wright, PLLC, Commercial Transactions Attorney (2001-2004)