Edwin Eisendrath, Former CEO, Chicago Sun-Times

“All my jobs helped build communities and have been impactful. I never lost sight of who should benefit from a life of work.”

August 2018

From Chicago to England to the Middle East, Edwin Eisendrath has worked and lived all over the world, which has helped shape him into the extraordinary leader he is today. As the former CEO of the Chicago Sun-Times, Eisendrath used his leadership skills to reinvent the organization, aiming to better connect the Chicago community in innovative ways. Some might have shied away from taking leadership of a financially-struggling company, but he assumed the role with grace and wisdom. He built meaningful community partnerships to better the future of the Chicago Sun-Times as well as the city.

Eisendrath studied philosophy in college, attending Harvard University for his undergraduate degree and National Louis University for his graduate degree. He has worked in a variety of industries throughout his career, from academia to politics. This diverse career informs his viewpoint that travel is “not collecting postcards—it’s changing the way you think,” as he puts it. Switching careers several times has given Eisendrath a different perspective on what it means to be a leader, and he frequently draws on his liberal arts foundation to continue growing with every opportunity—a key element of his leadership style.

Connecting with Purpose and Meaning

“All my jobs helped build communities and have been impactful. I never lost sight of who should benefit from a life of work.”

When most people think about their dream job, it often involves positively impacting the world and contributing to an overall greater good. Spanning multiple industries, Eisendrath considers each of his roles as dream jobs, because they all held purpose and incorporated an element of what he considers civic responsibility to a larger community.

As the former CEO of the Chicago Sun-Times, Eisendrath was grateful for the opportunity to learn more about and give back to the city he grew up in. He calls this “growing where I was planted,” noting that helping others in one’s community facilitated his discovery of his own leadership style. Learning how to lead means helping others grow their communities. “Don’t step outside your comfort zone,” he notes. “Grow your comfort zone.”

Awakening Leadership at All Levels

Having a background in teaching, Eisendrath applies those core skills to every leadership role. Part of this leadership style means placing full trust in his employees and knowing that they can produce the best results without micromanagement. He never had the “I can do everything” mentality with any role in his career. “No one is so smart that they know everything,” says Eisendrath. “There is always someone else out there that has thought about this more than I have.” Eisendrath maintains his passion for teaching as a business leader and loves empowering his employees to exercise and grow their talents.

The Chicago Sun-Times’ editors and writers are breaking the traditional newspaper mold by sharing powerful messages in unique ways. From printing a blank front page to show what the city would be like without newspapers to developing a campaign called “31 Bullets” to arm people with information they need to fight gun violence, Eisendrath resiliently led his team with the creativity he cultivated in his diverse background. His goal as a leader is to encourage his employees to think creatively about how best to connect those in the Chicago community to each other.

Empowering Others

In addition to connecting with purpose and meaning to awaken leadership at all levels, Eisendrath has focused on transparency and truth in his advisory positions. He often encourages those around him to be determined and break through the obstacles that get in their way. By focusing on the facts and delivering an honest perspective, Eisendrath and his team informed the public. His scrupulous attention to detail shines through in another daily mantra: “Make it matter,” he says. “What you do every day can make a difference.”

Eisendrath finds partnerships a particularly strong way to maintain transparency while also making one’s work count. Partnering with others to make a difference and gain expertise “build[s] bridges to understand the fences” that constrain Chicago and world communities. Using these bridges, an informed public can begin to make the necessary changes to alter their communities for the better—both in Chicago and around the world.

“Never, never, never quit.”

In a world where younger generations expect companies and governments to act with purpose and positively drive the world forward, Eisendrath is the kind of leader people want and need. Humble, and above all else, a teacher, his mission in leadership is to act with purpose and to show others how to do the same. The communities he built and continues to build are armies of leaders sans CEO titles, each empowered to make a lasting impact.


Interview By Jacquelyn Drust & Rachel Kesseler & Alexa Ohm

Fast Facts

Chicago, IL
Previous Experience
CEO of Chicago Sun-Times
Managing Partner for StrateSphere
Founder of YellowBike
Managing Director for Huron Consulting Group
VP Academic Affairs for Kendall College
Candidate for Governor of Illinois
Vice President of UNext.com
Receiver at Chicago Housing Authority
Federal Regional Administrator for US Dept. of Housing and Urban Development
Alderman for City of Chicago
Most Admired Leader
Artensia Randolph
5 Things He Can’t Live Without
Family, Dog (Winston), Books, Piano, Democracy

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