The Executives' Club Of Chicago

Member Spotlight: Megan Burke Roudebush

Megan Burke Roudebush-Headshot

Megan is a native New Yorker, but wasted no time expanding her network when she moved to Chicago by joining The Executives’ Club of Chicago in 2010. Megan is the Managing Director of Compliance at National Flood Services and the CEO and Founder of keepwith®, her start-up that teaches networking to companies, organizations and at virtual and in-person conferences. When asked about her favorite moment at The Club, Megan shared her experience at the “For Women by Women” program this past December. Listening to the insights of female founders and venture capitalists left her feeling inspired and empowered to continue pursuing her own endeavors. Check out more on Megan and her involvement with The Club below!

What about your work, company or role makes you most proud?

As a regulatory compliance leader, I am proud to serve in a capacity that focuses on prioritizing integrity in the marketplace. As a start-up Founder and CEO of a company that teaches networking, I am proud to have created a company whose mission is to help people build strong and authentic relationships, both in-person and digitally.

What is your favorite binge-worthy show or podcast?

Show: Chicago PD
Podcast: Super Women (Rebecca Minkoff's podcast featuring impressive female founders)

What was your first job? What lesson did you learn that you will carry with you?

My first job was unpaid. From the time I was 8 until the time I was 18, I was a professional reporter and editor for a kids' news service, interviewing adults and kids all over the globe about issues that matter. As a kid journalist, I learned the importance of caring about the world around us and how much we learn when we ask open ended questions. I carry those two lessons with me to this day.

Who was the best boss you ever had and why?

Jeannie Lewis, Senior Compliance Counsel at William Blair, was the best boss I ever had. She was the Deloitte Partner who hired me to join the firm's global regulatory practice. Jeannie is the most knowledgeable person I know when it comes to regulatory compliance, a strong leader and a genuine and kind human being. Plus, she is hands down one of the coolest people I know.

Can you share a time when you had to reinvent yourself, your product/service or your brand?

keepwith® has always been a start-up that has prioritized teaching people how to network well. This has largely involved supporting people as they meet others in-person. In response to the COVID pandemic, we have adjusted all of our service offerings to be available in virtual and digital formats. This was something that tested my comfort zone (and my understanding of true networking) and this innovative moment in response to a crisis was exactly the right move.

What’s your best “work from home” life hack?

Shower in the morning to start your day and create that "I am going to work" routine feeling. Shower at night to separate your work day from your personal time.

What drew you to Chicago as a business or personal home?

I moved to Chicago in 2010, after law and business school. At the time, the global markets were recovering from the financial crisis in 2008 and 2009 and traditional legal roles were not widely available at the time. Since securities and compliance were my passions, I took my first out of law school job as a bond analyst at Moody's. With every career pivot (I have made moves every few years), I have had opportunities to move from Chicago. My first after law school job brought me here. The neighborhoods, the diversity, the public transportation, the arts scene, the restaurants and the supportive networking vibe that is unlike that of any other city is what has kept me here.

Among the people you work with, who inspires you and why?

keepwith®'s Administrator Jennifer Grackin Steinberg inspires me. Jenn and I have known each other for over 20 years. We met as undergraduates at Bryn Mawr College, where she was my boss for my work study job in the dining hall. Years later, Jenn assumed the role of keepwith®'s Administrator and she has been instrumental in the growth and expansion of our start-up. Her judgment is sound, communication is honest and her overall approach to research, project management and follow-up make her a true rockstar. She inspires me every day and keepwith® could not be keepwith®.

As Megan highlighted, open ended questions are essential to nurturing a relationship and starting one. We would love to hear from you and highlight your achievements and tips in our member spotlight. To be featured or to recommend another member of The Executives’ Club to share a spotlight, please contact our team at