IT Consultancy Contract Lawyers for Naperville, Illinois

I am a solo-practitioner with a practice mostly consisting of serving as a fractional general counsel to growth stage companies. With a practical business background, I aim to bring real-world, economically driven solutions to my client's legal problems and pride myself on efficient yet effective work.

A seasoned attorney with deep General Counsel experience and a flexible, business-minded approach to legal leadership. Skilled in collaborating with product, sales, operations, finance, and executive teams — not just to mitigate risk or ensure compliance, but to enable growth, innovation, and efficient deal execution. In my current practice at GCBench, I offer scalable, on-demand counsel tailored to organizations’ changing needs. Legal rigor is combined with operational sensibility, making guidance a facilitator rather than a hurdle. Whether structuring transactions, advising on regulatory matters, or shaping policies, legal strategy is aligned tightly with business objectives.

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.

I received a bachelor’s degree in philosophy from Northwestern University in 1996 and then got my JD at University of Illinois College of Law in 1999. I have been a lawyer helping people with legal issues in the United States and Internationally since then. That includes drafting and reviewing contracts. I am also passionate about helping small and medium businesses with trademark registration and trademark-related legal projects. The law can be confusing and complicated for people, and I am passionate about providing professional legal services to my clients while simultaneously making the legal process less confusing and stressful for them. My goal is to help clients navigate through both good and difficult times by tailoring my skills, experience, and services to their specific needs.

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.

I attended the University of Illinois- College of Law on a full merit scholarship. While in law school, I was a 711 Attorney at the Lake County State's Attorney's Office, specializing in traffic and misdemeanor cases. After graduation, I served as in-house counsel for one of the largest insurance companies in the world, managing thousands of cases from initial intake to trial. Upon leaving this position, I accepted a role as Legal Counsel to the Illinois Senate Minority Leader. There, I advised Senators on legislative matters, labor and employment law, and complex constitutional questions. After leaving public service, I accepted a role at a mid-size Chicago-based law firm, where I practice insurance defense and litigation. In addition to this, I also serve as outside general counsel to a food brokerage business, where I handle all of their labor and employment matters.

Mr. McElvenny has extensive experience handling and developing strategy for complex commercial and real estate cases. He’s drafted hundreds of complaints ranging from simple breaches of contract to complex commercial claims including breach of fiduciary duty, constructive trusts and misappropriation of trade secrets. He has an excellent record in trial, arbitration and mediation. He also has significant experience in motion practice in both state and federal court. Through his work in corporate law, Mr. McElvenny has developed considerable experience with Limited Liability Company member disputes and general corporate governance. He’s drafted a number of industry-specific documents such as Operating Agreements (for Limited Liability Companies), commercial leases, settlement agreements and employment contracts. Mr. McElvenny has also represented criminal defendants in felony matters and assisted in the defense of civil matters arising from alleged SEC violations. He has represented individuals appearing before the Illinois Department of Professional Regulation as a result of SEC proceedings. After graduating with a B.A. in Philosophy, Mr. McElvenny proceeded from Loyola University-Chicago to DePaul University College of Law, receiving his JD from that institution in 2002. In 2010, he earned his Master’s of Science in Accounting from Loyola University-Chicago’s Graduate School of Business. Mr. McElvenny was selected to Illinois’ Super Lawyers Rising Stars in 2010, 2012 and 2013.

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.