At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the CRM space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Sam Kann
Founder & CEO of MyColLife
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About MyColLife: Welcome to MyColLife, world’s first Student Social Network and Social Relationship Management (SRM) services technology.

Angela Cobb
CEO of FirstGen Partners LLC
Angela Cobb is CEO of FirstGen Partners LLC, a firm that helps organizations and individuals evolve and adapt to maximize their impact, she has two decades of experience in recruiting, diversity, community development, strategic philanthropy and change management. Before launching FirstGen Partners LLC, Angela served as the first Chief Diversity Officer at Teach For America – the country’s national teaching corps – where she led organization-wide diversity and inclusion efforts. Angela also has extensive experience launching and leading new philanthropic efforts and business ventures through her work at FirstGen, and in various senior roles at Allstate, Monster, Deloitte, and United Way. Angela is a member of the board of Umoja Student Development Corporation, serves on the Advisory Board of the Chicago Children’s Museum, and is a member of the current cohort of the Pahara-Aspen Education Entrepreneurs Fellowship, a part of The Aspen Institute’s Crown Fellows Program. Past leadership and honors include serving as a Trustee of the University of Notre Dame and as a member of the Advisory Council for the University’s Mendoza College of Business. Angela was also a 2008 Leadership Greater Chicago Fellow. A graduate of Northwestern University’s Kellogg School of Management, where she received an M.B.A. in Organizational Behavior and Strategy, Angela received a B.B.A. in Accounting from the University of Notre Dame.
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About FirstGen Partners LLC: FirstGen Partners provides consulting, advisory, and coaching services.

Kris Kehler
Founder & Chief Executive Officer of DebtPayPro
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About Debt Pay Gateway Inc, DebtPayPro, Radix Software, Supervest: DebtPayPro exists to provide all encompassing tools to help businesses help consumers.

Christopher Olofson
Founder and Chief Executive Officer of Olofson Technology Partners
Chris Olofson is an established senior executive in the legal technology services field and has developed legal technology innovations since 1992.
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About Olofson Technology Partners: Olofson Technology Partners provides specialty technology solutions and professional services within the legal profession.
Charles Craigmile
Chief Executive Officer of Revenova
Charles Craigmile is a seasoned executive who has had significant P&L experience in leading organizations to be more efficient across the supply chain throughout the US, Asia and Europe in key operational metrics such as customer service, inventory turns, on time shipping and profitability as well as building sales and operations to new levels of financial results.
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About Revenova: Revenova TMS is a 100% cloud CRM based transportation management system for shippers, brokers and third-party logistics (3PL) companies.

Daniel Hayes
President, CEO of HealthCall
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About HealthCall: HealthCall is a company providing cloud-based solutions to enable the communication between healthcare professionals and patients.

Salvatore DiBenedetto
Chief Executive Officer of Malu Marketing
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About Malu Marketing: Social Media Growth Agency
Daniel Newman
Co-Chief Executive Officer & Co-founder of V3 Broadsuite
Daniel Newman is a 3x Best Selling Author, Futurist and Insight Partner to the world’s largest brands. Daniel delivers a highly compelling and memorable experience, which audiences long for. With a breadth of topics to include Technology, Social Media, Marketing and Sales, Daniel brings a diversity that is rare yet highly desirable in a keynote speaker. Over the past decade Daniel Newman has delivered more than 250 keynote, panel discussions, workshops and live interviews throughout North America. With a focus on the rapid convergence of marketing and technology, Newman’s sessions cover the gambit of Social Media, Mobility, Cloud, Big Data; all with measurable and meaningful ties to creating better customer experiences. Over the past 3 years Newman has been recognized by some of the world most recognized media outlets and brands as a top influencer in subjects such as Leadership, Employee Engagement, Human Resources, Technology and Marketing. With his uncanny ability to tie together technology trends and business transformation, Newman is trusted by brands such as IBM, Dell, SAP and Oracle to provide his unique perspective on topics business digital transformation and social customer service. With a mix of quick wit and humor, Daniel is able to rapidly build connections with almost any audience. As a former CEO of a midsize company, Newman also understands how to integrate speaking topics with an audiences most pressing needs. Author of 2 Amazon Best Selling Books, Newman is a trusted voice found weekly on Forbes, Huffington Post and Entrepreneur Magazine. If your company or organization is looking for “Wow” at your next event, then you have come to the right place. Daniel doesn’t hold back, bringing excitement and valuable insight for every audience he engages.
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About V3 Broadsuite: V3 Broadsuite is an innovative agency specializing in the digital space.
Matt Wolf
Founder / CEO of Antonym
Matt Wolf is the founder and CEO of Antonym. He is also a partner at Dandelion. Prior to that, Matt has held positions at General Sports and Entertainment, United Talent Agency, and Thunder Road Pictures.
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About Antonym: Antonym is a vertically integrated emerging technology agency.