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Derek Simmons

AI Strategy · Digital Transformation · Media Executive

Minneapolis, MN

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summary

Executive with 30 years in media, digital strategy, and AI. Led teams of 55+ across editorial, product, and revenue. Generated $20M+ at the Star Tribune as its first and only Chief Creative Officer. Contributed to 4 Pulitzer Prize-winning teams. Now consulting on AI strategy and building AI-native products at CW Strategies.

core competencies

AI Strategy & Integration Digital Transformation Revenue Growth Audience Development Product Strategy Content Operations Cross-Functional Leadership Team Building Brand Strategy Visual Storytelling Media Innovation Change Management

experience

Founder & Principal Consultant Nov 2024 – Present
CW Strategies LLC, Minneapolis, MN
  • Founded AI strategy consultancy serving media and mid-market organizations
  • Delivering strategy, audience development, and AI integration for active clients
  • Built AI conversation platform, training apps, and content systems from concept to production
  • Developed repeatable methodology: assess, build capacity, transfer ownership, exit
Executive Director, New Products & Digital Strategy Feb 2023 – Oct 2024
Star Tribune Media Company, Minneapolis, MN
  • Led enterprise AI strategy, integration roadmap, and governance framework
  • Senior leadership team redefining company mission, values, and digital presence
  • Led digital product evolution driving audience and subscription revenue growth
  • Launched sponsored content franchises generating seven-figure annual revenue
Chief Creative Officer & VP / AME, Visuals Dec 2013 – Feb 2023
Star Tribune Media Company, Minneapolis, MN
  • First and only CCO/VP in 150-year company history; created the role
  • Generated $20M+ in subscription, sponsorship, and advertising revenue
  • Led 55-person team across digital, mobile, print, and events
  • Pulitzer recognition, Top 3 worldwide design ranking (Society for News Design)
Deputy Design Director Mar 2007 – Dec 2013
Los Angeles Times, Los Angeles, CA
  • No. 1 worldwide design ranking (SND) for six consecutive years
  • Pulitzer Prize contributions for investigative and multimedia work
  • Led visual journalism teams through digital transition and platform expansion

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

what colleagues say

“I could not have imagined a better partner.”

“A forceful agent for change. Congenial, smart, diplomatic but also inspiring.”

“A leader needs to articulate a vision, bring it to life, then share credit. This is what Derek does.”

Full recommendations and references available upon request.