← Back to CW

Derek Simmons

Three decades in media, sports, and technology. Former Chief Creative Officer who generated $20M+ in revenue. Now building AI frameworks for human-centered organizations navigating complexity and change. Available for consulting, advisory, and fractional roles.

Connect

LinkedIn Email GitHub Substack

Experience

Founder & Principal Consultant Nov 2024 - Present
CW Strategies | AI Strategy and Media Transformation
  • AI strategy and media transformation consulting for organizations navigating complexity and change
  • Building CW, Coach D, and The CW Standard — frameworks for human-centered AI collaboration
Executive Director, New Products & Digital Strategy Feb 2023 - Oct 2024
Star Tribune Media Company, Minneapolis
  • Championed AI strategy establishing integration and innovation roadmap
  • Served on senior leadership team redefining company mission, values, and digital presence
  • Led digital-product evolution driving significant audience and revenue growth
  • Launched franchises generating seven-figure annual sponsorship support for journalism
Chief Creative Officer & Vice President Jun 2017 - Feb 2023
Star Tribune Media Company, Minneapolis
  • Directed multiyear transformation integrating data-driven content and audience development
  • Achieved Pulitzer recognition for investigative projects and Top 3 worldwide design ranking
  • Generated $20M+ in subscription, sponsorship, and advertising revenue
  • Led 55-person editorial and creative teams across digital, mobile, print, and event platforms
Deputy Design Director Mar 2007 - Dec 2013
Los Angeles Times Communications
  • Achieved No. 1 worldwide design ranking (SND) for six consecutive years
  • Contributed to Pulitzer Prize team recognition for investigative and multimedia projects

Education

B.S., Journalism & Mass Communication - Kansas State University
Executive Certificate, Customer Experience - Minnesota State University Mankato
Executive Training - Poynter Institute, Yale University, Leiden University

Recommendations

"Derek consistently demonstrated exceptional strategic thinking and cross-functional leadership capabilities essential for executive-level roles... He was instrumental in developing revenue-generating initiatives that contributed to the generation of more than $20 million in revenue."

Michelle Mueller
Senior Vice President, Human Resources

"Derek has been crucial to the Star Tribune's uncommon success and stability in a perilous era... He is not a leader who merely manages whatever arises - he keeps daring to break new ground."

Rene Sanchez
Executive Editor and Vice President

"Derek may be the most productive and innovative person I know... He's a born strategist... He sees the big picture while keeping a firm grasp on the details."

Monica Moses
Executive Director, Product Innovation