Keep Proving Yourself

Michael Cronin’s dedication to constant improvement has his legal team delivering real results at Classified Ventures

Michael Cronin VP, Chief Legal Officer &  Corporate Secretary Classified Ventures Location: Chicago, IL   Career Advice: “Listen to the people who are already experts. Become a ghost. See and observe everything, and talk less than you listen.”
Michael Cronin
VP, Chief Legal Officer &
Corporate Secretary
Classified Ventures
Location: Chicago, IL
Career Advice: “Listen to the people who are already experts. Become a ghost. See and observe everything, and talk less than you listen.”

Michael Cronin has no problem proving himself—after all, he’s had to do it time and time again. Cronin quit his job as a litigator after discovering how aggressive and draining procedural work and courtroom arguments could be. He wound up on an unexpected hiatus, staying with friends in Central Illinois, when he interviewed at a small software company called Wolfram. Cronin was hired and became staff attorney for a firm that had never had an in-house counsel before. Cronin, who had been licensed for just over 12 months, dug in. He poured over legal texts, teaching himself software licensing and other relevant legal issues while learning the software industry inside and out.

Since 2007, Cronin has worked at Classified Ventures, a Chicago-based company that owns and operates and He became vice president, chief legal officer, and corporate secretary in March of 2013, and now manages all legal matters, relying on a few trusted principles that have become the theme of his career.

1. Learn something new every day

Cronin has been learning since day one at his first job. “I had no other choice,” he says. “I didn’t know anything, so I had to soak up all the information I could along the way, learn on the job, and find out what people needed from me.” That’s a strategy that’s served him well at companies from Level 3 Communications, where he handled contracts and dispute resolution issues, to Classified Ventures, where he manages a complete legal team.

Lawyers learn most effectively on the job by subscribing to industry groups and publications, staying connected to their peers, and interacting with internal business leaders as much as possible—and the opportunity to learn and grow is what first attracted Cronin to Classified Ventures. “We’re an exciting and growing digital-media company filled with talented people,” he says. “It’s a great experience to learn from them and be challenged by their innovations.”

Leading Classified Ventures’ legal function has enabled the veteran attorney’s commitment to continuous learning as the company pursues various deals or explores new technologies. While Cronin started in contract and licensing work, he now touches all legal matters for the organization, including vendor agreements, regulatory and governance issues, and employment law.

2. Never be afraid to take risks

Originally created as simple online classifieds, and are owned as a joint venture by some of the biggest media companies in the country: Tribune Company, Gannett, The Washington Post Company, The McClatchy Company, and A.H. Belo Corporation.

Classified Ventures was founded as a response to the decline of print classified advertisements in the late 1990s. As those ads migrated to the web, Classified Ventures’ creators made a big bet that they could capitalize on the transformation by going digital. Today, the sites’ content is rich, interactive, and social, providing information to car and apartment shoppers and valuable advertising to car dealerships, auto manufacturers, property managers, and more. Strategic risks and smart moves have allowed both companies to grow rapidly, providing a handsome return to the original investors. Classified Ventures now has more than 1,500 employees in 43 states.

Cronin is a good fit at a company that has risk-taking at its very core, because he too welcomes the opportunity to bet on himself. “Nobody was there at first to tell me I was doing something wrong,” he says. “I’m sure I made mistakes, but I had to believe in myself and relish the space to grow and learn and be willing to mess something up. Eventually I saw progress and realized I could do it.”

The early years of working things out on the fly shaped the young and developing lawyer. It created an attorney willing to go out on his own—even when that requires making a bold move. “The single most important skill you can cultivate as a young lawyer is the willingness to take a risk,” Cronin says. Lawyers are often expected to research an issue, discover a solution, deliver bad news, and provide valuable counsel. Often, there’s a lot at stake.

3. Realize that you are providing a service

Cronin compares his legal team to a customer-service organization. He and his colleagues take requests, contextualize them, analyze issues, and return a solution. “The hardest thing for firm lawyers that come in-house is understanding the service they provide,” he says. In-house lawyers are there in a support role: their clients may be internal, but the model remains the same. A coherent legal team trained in business operations and ready to serve a company’s needs helps push a growing business forward.

4. Keep proving yourself

Getting an in-house job is one thing, but Cronin says each attorney should constantly work to add value to his organization. “Proving you belong is something we do every day,” he says. “We should look at ourselves as probationary.” At each stop along his career, Cronin has found business executives who expect the legal team to ask questions and learn the business. “A good in-house lawyer will understand what is important to the client and make this their priority,” he says.

In doing so, a legal team becomes a set of trusted advisers to the business side of the company. “We can move the business forward in real ways,” Cronin says. Lawyers, after all, are trained to look around corners and turn issues inside out in a way that may not be so obvious to those in business roles. Legal training, in Cronin’s words, can be “put to the service of the enterprise in a way that’s not always intuitive.”

Although Cronin has been with Classified Ventures for seven years, he still follows his own rules. “I really am still learning, and I learn best from my team,” he says. As he trains senior counsel, junior lawyers, and paraprofessionals in all aspects of the rental and auto industries—from vendors to web analytics—he also asks each team member to share his or her own expertise, like finance, real estate, intellectual property, or regulatory compliance. His team, Cronin says, buys into the approach because they see him participating every single day, and his track record proves it works.

Editor’s Note: At time of press, is for sale and may no longer be owned by Classified Ventures at date of publication.