Technology Leader Profiles

The Digital Technology Leader Series is a profiling of the most influential people in Chicago's digital technology community. The goal of the series is to inspire entrepreneurs and founders running digital technology startups in Chicago and share with the nation Chicago's most influential digital technology leaders.


September 2012
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Andrew Sieja | Founder, President & CEO | kCura

"Stick to your guns. Don’t worry about what’s hot. Don’t worry about your competition and what they’re doing."

August 2012
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Eric Lunt | CTO | BrightTag

"The risk of taking the leap pales in comparison to the opportunity cost of not leaping."

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Marc Kiven | Founder & Chief Revenue Officer | BrightTag

"Surround yourself with really smart people."

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Mike Sands | President & CEO | BrightTag

"If you're going to be an entrepreneur, don't do it alone."

July 2012
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Jon Schepke, Founder & President of SIM Partners

"Culture is everything… it will help get you through the tough times and it will make the good times more fulfilling."

June 2012


Michael Alter, President of SurePayroll

"Learn to sell!"



David Ormesher, President and CEO of closerlook

"Confidence is the electricity of life. Without confidence it's hard to get out of bed in the morning. With confidence you can conquer mountains. As an entrepreneur it's important to protect your confidence"

April 2012


Pat Ryan, CEO of INCISENT Technologies

"When focused on the big audacious goal, make sure you know how to achieve quick wins along the way. It keeps you and employees motivated"



Brian Spaly, CEO of Trunk Club

"The servant leader paradigm. As a CEO, it is your job to serve your team and provide the resources they need to be effective."

April 2012


Zach Kaplan, CEO of Inventables 

"Always ask why."

March 2012


Amanda Lannert, CEO of The Jellyvision Lab 

"...early in your career, the people you work with are more important than the company or the project that occupies your time in terms of how much you can learn. So choose your managers and mentors wisely."

February 2012

Bill Ready, CEO of Braintree

"...How important it is to surround yourself with great people.  I was fortunate enough to stumble into situations with great people early in my career and later learned how valuable it is to proactively seek out those great people."

Bryan Johnson, Founder & Chairman of Braintree

"Be true to yourself. Life is so personal and contextual that it's best to carve your own path.

Sean Finnegan, CEO and Founder of The C4 Group

"...promotion is not always a good thing. The notion that you can only succeed through climbing the corporate ladder is a fallacy. I now recognize that it is also best to “rise” while..."

January 2012

Macolm Lotzoff, CEO & Co-founder of INXPO 

"The best investment you can make is in your education." What you know is one of the only things that can never be taken away from you. To this day..."

Dave Husain, CEO of Leapfrog Online 

"Choose your Team like your business depends on it…because it does."

Howard Tullman, President & CEO of TFA

"A great idea and a lot of hard work are at least 80% of the story, but without good timing and good luck, you’ll never..."

Sam Yagan, Co-Founder & CEO of 

"My first computer science professor, Margo Seltzer, encouraged me not only to continue taking computer science classes but also to apply for a position as a teaching fellow in her class the..."

December 2011

Gian Fulgoni, Chairman & Co-Founder of comScore 

"For me, Rudyard Kipling had the best advice, which is that creativity and new ideas are the lifeblood of entrepreneurs..."

Irv Shapiro, CEO and CTO at Ifbyphone

"Successful communication requires much more than emails, tweets, or even talking to someone. Successfully communicating is all about listening. Actively listening. In active listening you may be starting a conversation or..."

Mark Achler, SVP Strategy & Innovation at Redbox

"At the end of the day, no matter how good the idea or how big the opportunity, if you don’t assemble the very best team the opportunity will never reach its full potential."

Talia Mashiach, CEO and Founder of Eved

"Challenges will be overcome and they will be the best learning experiences."

November 2011

Matt McCall, Partner at New World Ventures

"Entrepreneurship and venture capital are 90% people and 10% strategy and insight. I originally believed that the key to success was knowing the answer and figuring out the path to..."

Rishad Tobaccowala, CIO at Vivaki

"Nobody is as passionate about what you do as you and nobody else can see the possibilities like you do. Navigating the chasm between your idea and their reality is the key to success and peace of mind."

Larry Kaplan, CEO of Navteq

"...products and services don’t build businesses.  People do.  The people are most important.  And, of course, you still need great strategy and execution!


Alex Campbell, CEO & Co-Founder of Vibes Media

"...Just how crippling the fear of failure can be for an organization.  By nature, we all want to look good or avoid looking bad which really prevents us from trying new things that might fail."

Matt Moog, CEO & Founder of Viewpoints 

"Necessity is the mother of invention...creating a sustainable competitive advantage should be at the heart of your strategy." 

Troy Henikoff, CEO & Co-founder of Excelerate Labs

"In a startup, success is more correlated with what you choose not to do than what you choose to do."


October 2011

Jai Shekhawat, CEO & Co-Founder of Fieldglass

" companies get eaten from the bottom up. Think Salesforce and Siebel in the CRM space. Software invariably gets overbuilt due to pressure to keep adding functionality and eventually new players emerge with..."

Tim Fagan, COO of CouponCabin

"...the key to being a successful outwardly-facing business development leader is to know the inside of your own operation better than anyone."


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