DEREK SIMMONS
Transformative Executive | Founder @ CWS | Ethical AI & Digital Strategy
Visionary executive and founder with 15+ years leading digital transformation, AI strategy, and ethical innovation. Generated $20M+ in new revenue by building high-performing teams and frameworks that bridge human wisdom with technology. Renowned for turning complex concepts into business value and fostering environments where technology amplifies, not replaces, human potential. Passionate about coaching leaders and championing ethical AI for sustainable growth.
PROFESSIONAL EXPERIENCE
Founder (Part-Time, In Development)
Claude Wisdom Strategies | Nov. 2024–Present
- Developing innovative conversational AI and strategy frameworks as a personal R&D initiative, with a focus on ethical, human-centered technology.
- Exploring methodologies for knowledge management and creative flow, applying insights to consulting projects and future full-time roles.
- Building systems and tools that enhance decision-making and productivity, with the goal of translating these learnings to enterprise environments.
This project is a part-time, exploratory initiative while seeking full-time executive opportunities.
Executive Director, New Products
Star Tribune Media | March 2022–Oct. 2024
- Presented a comprehensive AI strategic plan, leading to the formation of the company's first AI Task Force.
- Conceived the "Minnesota Star Tribune" rebrand and played a key role in the eight-month digital relaunch, elevating brand recognition and digital engagement.
- Led enterprise-wide initiatives impacting 1,000+ employees, driving digital transformation and operational efficiency.
- Designed and implemented the SalesGPT solution with Krista.ai, reclaiming up to 2.5 work-years annually for the sales team.
- Generated $5M+ in new revenue through innovative content platforms, including a successful sports betting launch, sponsored content, and affiliate marketing.
- Directed cross-departmental product development and established standards for cohesive, ethical implementation.
Chief Creative Officer / Vice President
Star Tribune Media | June 2017–March 2022
- Led design innovation as the company's first CCO, driving digital subscription growth to 100,000+ (top 6 nationally) and enhancing audience engagement.
- Conceived and executed the "Minnesota Star Tribune" rebrand and led the eight-month digital relaunch, elevating brand recognition and digital engagement.
- Pioneered the Media Franchise Model, generating $15M+ in new revenue through innovative content structures.
- Managed $2M+ annual budget and cross-functional teams, including newsroom, product, and business operations.
- Contributed to a revenue turnaround in 2021, shifting from a $900K deficit to a $1M surplus in a single fiscal year.
- Drove the Star Tribune's 150th anniversary campaign, including statewide events, media partnerships, and award-winning brand activations.
Assistant Managing Editor, Visuals
Star Tribune Media | Dec. 2013–June 2017 (continued through 2020, concurrent with CCO/VP)
- Built and led high-performing, award-winning visuals teams, maintaining a perennial Top 5 global ranking by the Society for News Design.
- Led newsroom through digital and print redesigns, including the acclaimed startribune.com relaunch and mobile site.
- Contributed to Pulitzer Prize-winning and finalist projects, and numerous national and international accolades.
- Hired and developed 50+ journalists during a period of rapid organizational change.
Business-side Strategic Assignment
Star Tribune Media | 2020–2022
- Selected for a cross-functional business-side rotation to drive innovation and revenue growth, collaborating with product, sales, and executive teams.
- Applied newsroom leadership and creative strategy to business operations, supporting the company's digital transformation and EBITDA goals.
- Navigated the challenges of remote leadership during the pandemic, maintaining momentum and communication across teams.
Career Highlights
- Recognized as one of the world's top visual journalists and media leaders, with 1,000+ awards for excellence in design, innovation, and leadership.
- Led and designed award-winning products and initiatives for more than three decades, ranging from branded t-shirts to industry-leading digital apps and platforms.
- Launched 20+ digital products and MVPs with proven ROI, driving $20M+ in new revenue and industry-leading engagement.
- Built and governed brand frameworks impacting 1,000+ employees and 30M+ monthly visitors.
CORE COMPETENCIES
Strategic Innovation
Driving breakthrough solutions by connecting vision with practical execution, from concept to market.
Change Management & Transformation
Leading organizations through complex change, building resilient teams and systems that thrive in evolving environments.
AI Ethics & Human-Centered Technology
Developing frameworks that ensure technology amplifies human capability, with a focus on ethical, sustainable implementation.
Coaching & Leadership Development
Empowering leaders and teams through coaching, mentorship, and a focus on growth, adaptability, and high performance.
AI RESEARCH & DEVELOPMENT
- Led 1,500+ hours of research on large language models, tracking capability evolution and developing enterprise applications.
- Designed and implemented SalesGPT automation with Krista.ai, reclaiming up to 2.5 work-years annually for the sales team.
- Developed ethical AI frameworks and evaluated strategic partners for enterprise-wide AI adoption.
- Advanced human-AI collaboration approaches, ensuring technology augments human judgment.
- Leveraged tools including Claude, GPT-4, Cursor, Obsidian, Notion, GitHub, and more.
- Explored strategic AI partnerships with AWS, Cohere, SAP, MuleSoft, Zeta Global, and Sportradar.
The CW Standard Framework
Developed the CW Standard, a systematic methodology for ethical AI integration that prioritizes human values, continuous learning, and transparent leadership. Provides clear, adaptable guidelines for leveraging AI while maintaining human agency and fostering measurable, ethical innovation.
BOARD LEADERSHIP & COMMUNITY IMPACT
- Minnesota State University–Mankato: Customer Experience Advisory Board Member (Apr 2023–Dec 2024)
- East Ridge Athletic Association: Basketball Board President, Woodbury, MN (serving 200+ families)
- Sports Coaching & Player Development: 10+ years in Minnesota; 75% college basketball scholarship success rate (Summer 2023)
- International News Media Association: Member (May 2023–Present)
- Saint Therese: Pet Therapy Volunteer, senior living community (2024–Present)
- Ruff Start Rescue: Advisory Board Member (2023–Present)
- Community Engagement: 75+ volunteer hours annually as keynote speaker, digital competition judge, workshop instructor, mentor, coach, and board member
EDUCATION & PROFESSIONAL DEVELOPMENT
MIT, Artificial Intelligence & Data Science Program
Admitted, 2025 cohort
University of Southern California, Master of Communication Management
Admitted, 2022
Kansas State University, Bachelor of Science in Mass Communications
- Managing Editor and Head of Design, Kansas State Collegian
- Correspondent for the Associated Press, Kansas City Star, Wichita Eagle
- Student Ambassador & Keynote Speaker, A.Q. Miller School of Journalism
Additional Professional Development
- Yale University, The Science of Well-Being (Coursera Certificate, May 2020)
- Leiden University, De-Mystifying Mindfulness (Coursera Certificate, May 2020)
- Poynter Institute, Leadership Academy, St. Petersburg, Florida