Consulting Services Contract Lawyers for Illinois

Trusted legal counsel and business advisor to businesses and executive teams in the software, financial, and technology industries. Practice areas include commercial transactions, licensing, SaaS/PaaS/IaaS delivery models, software product development, regulatory compliance, new business formation, employment matters, and general corporate matters.

Mathew Kerbis is The Subscription Attorney. He’s on a mission to affordably serve clients at scale via the subscription model and inspire attorneys to abandon the billable hour. He founded the law firm Subscription Attorney LLC after working for private practice law firms for nine years. His firm leverages automations and artificial intelligence to offer more accessible and reasonable prices like legal advice starting at $19.99/month and $49.99/page.

I provide practical, plain-English legal guidance to solopreneurs and small businesses who want to build strong foundations and make informed decisions with confidence. With 20+ years of experience—including 16 years in-house advising senior and executive leaders—I bring the insight of a trusted legal partner who understands how legal strategy supports long-term business growth. My clients walk away feeling supported, seen, and empowered. They know I genuinely care about their success and bring more than just legal knowledge—I bring a coach’s mindset, a problem-solver’s lens, and a commitment to helping them protect what they’ve worked hard to build. Whether you’re reviewing contracts, forming your business, protecting your brand, or need ongoing legal support, I’m here to deliver clear, actionable guidance and solutions that fit your business.

Navy veteran with 15 years experience practicing law in Chicago.

Financial Services, Business, Corporate, Personal Injury, and Healthcare. I've represented fortune 100 companies and defended individuals in personal debt litigation. Wide breadth of experience, ready to assist.

2008 - Present: Sole Practitioner – Dennis W. Winkler, P.C. Practice primarily in finance and business transactions, as well as commercial real estate transactions. Represent developers, investors, lenders, and businesses, in such matters as: corporate entity selection, drafting and negotiating complex asset purchase agreements, corporate mergers and sales, stock purchase agreements, and various other business contracts for closely related businesses. Involved in a variety of real estate developments, multi-family apartment buildings, construction and acquisition financing, commercial leasing, sophisticated workout transactions, joint ventures, and tax-deferred exchanges. Advise on tax and other savings incentives available to business owners and real estate owners in Illinois. Advise companies involved in related real estate activities such as sales, leasing, property management, brokerage, and construction. Tax experience that includes the representation of taxpayers in State and Federal controversies including: sales/excess tax disputes and responsible parties’ tax assessment protest. Additionally, Dennis has experience in the protest of real estate taxes of commercial and multi-family real estate. As a legal and business advisor, Dennis is committed to helping clients find, develop, and close deals that further their business objectives. Dennis regularly advises entrepreneurs and closely held businesses on matters incidental to their day-to-day business operations as well as their capital raising and start-up needs, corporate structure, private equity raises, and operating agreements. Much like general counsel, Dennis’s breadth of experience allows him to not only provide strategic planning and routine business transactional support to companies, but he also regularly advises on a number of unique issues facing companies by spotting issues and engaging specialists when needed, such as intellectual property, environmental, and bankruptcy counsel. As such, Dennis has been actively involved in sales and acquisitions of manufacturing companies, trucking companies, and logistics companies.

Senior experienced contracts/transactions attorney in the Software Technology space. Also very versed in general corporate legal matters relating to business operations.

Commercial Litigation attorney providing advice and counsel to management regarding employment related matters and risk management issues

I am a licensed attorney in Illinois, I am currently a Regulatory Compliance Analyst.

Sarah graduated magna cum laude from the University of Illinois College of Law in 2013. Prior to opening her own practice, Sarah worked in a large law firm defending corporate clients. She then transitioned to a smaller firm where her longing to serve clients in the surrounding community became evident. With her prior experience, Sarah opened her own firm in 2016 and has since served Lemont and the surrounding areas.