Executive Summary
Executive with 20+ years driving digital transformation and sustainable business growth across major metro media organizations. Led revenue diversification strategies generating $20M+ in new revenue while guiding cross‑functional teams through reinvention.
Leadership Experience
Executive Director, New Products & Digital Strategy
Feb 2023 – Oct 2024- 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- 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 through innovative products and collaborative partnerships.
- Led 55‑person editorial and creative teams across digital, mobile, print, and event platforms.
Assistant Managing Editor for Visuals
Dec 2013 – Jun 2017- Directed visual teams (20-25% of newsroom staff); elevated organization from no prior Top 25 finish to Top 10 within first year and perennial Top 3 worldwide ranking (SND).
Consulting Experience
Founder & Principal Consultant
Nov 2024 – Present- Trusted partner for organizational growth, executive leadership development, and strategic revenue diversification.
- Deliver 150–200% efficiency gains via AI‑accelerated research, producing $20K–$40K client savings per engagement while completing 6–8 weeks of analysis in half the time.
Earlier Experience
Deputy Design Director
Mar 2007 – Dec 2013- Drove product launches and rebranding campaigns strengthening market leadership.
- Achieved No. 1 worldwide design ranking (SND) for six consecutive years (2007–2013).
- Contributed to Pulitzer Prize team recognition for investigative and multimedia projects.
Core Competencies
Editorial Strategy · Newsroom Leadership · Revenue Growth · Audience Development · Digital Transformation · Brand & Content Partnerships · Crisis Management · Data‑Driven Storytelling · AI Integration · Talent Development
Education
B.S., Journalism & Mass Communication — Kansas State University
Executive Certificate, Customer Experience — Minnesota State University Mankato
Executive Training & Certification — Poynter Institute, Yale University, Leiden University, Trusted Coaches, Pet Partners
Board & Community Engagement
- Board leadership roles in athletics, animal welfare, and education
- High school and AAU basketball head coach, trainer, platform developer
- Pet therapy volunteer; professional consulting and mentoring
Professional 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... His ability to bridge editorial and business operations made him particularly effective during our digital transformation efforts."
Michelle Mueller
Senior Vice President, Human Resources | Star Tribune Media Company
"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. A leader needs to articulate a vision, meticulously bring it to life, then take care to share credit. This is what Derek does."
Rene Sanchez
Former Executive Editor | Star Tribune Media Company
"When I was put in charge of a complex, multi‑year change process, Derek Simmons was assigned as creative lead. I could not have imagined a better partner. 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
Former Executive Director, Product Innovation | Star Tribune Media Company