Derek Simmons
AI-Native Media Executive · Builder · Editorial Strategist
Woodbury, MN
summary
AI-Native Media Executive who spent thirty years in newsrooms before building an independent practice in late 2024 — production tools shipped under my own name (Coach D, claudewill.io, Option D), a short film directed and released, published essays on human-AI collaboration. Before that: first Chief Creative Officer/VP in the Star Tribune’s 150-year history, where I contributed to more than $20M in documented revenue over eight years (2017–2024, across that role and the next) and worked alongside four Pulitzer-winning teams. Built the editorial process behind a Pulitzer finalist that changed four laws, and the visual system the newsroom used for the 2021 Pulitzer for Breaking News. Earlier, Deputy Design Director at the Los Angeles Times — top winner worldwide, SND, for the better part of a decade. Based in Woodbury, MN — open to remote and hybrid roles in editorial direction, chief of staff, or AI strategy.
core competencies
experience
- Cascadia Media Company (Bellingham, WA) — monthly retainer, Sept 2025 through April 2026: visual strategy, audience development, editorial products, color-workflow system (Lightroom presets + Photoshop JSX), org structure analysis, AI ethics framework
- Built claudewill.io from scratch with AI-assisted tools — HTML, CSS, vanilla JS, serverless functions, Anthropic AI, Supabase; autonomous overnight agent pipeline
- Built Coach D — an AI basketball-coaching platform built around a cloned voice
- Shipped Battle o' Brackets (BOB) — bracket-based party game with voice host, March Madness theme, social sharing
- Directed lightning/bug — AI-assisted short film, released Mother's Day 2026, festival submissions in progress
- Author/editor, Being Claude — ongoing series on working with AI from inside the practice
- Built a sports betting content platform and a paid content platform
- Helped launch an entertainment franchise with a $1M sponsor, and worked directly with the sponsor on the creative
- Led Advertising Policy & Standards (Feb 2022 – Oct 2024) — a five-person team reporting to the Publisher and General Counsel; wrote company policy for regulated advertising categories including THC and cannabis, ran contract and policy reviews with internal and outside counsel, and negotiated content-vendor agreements
- Shipped earned-revenue product with the product team from scoping through launch and iteration, with product decisions informed by A/B tests run with the product and analytics teams
- Served as AI champion for sales, advertising, and marketing; senior leadership team
- Helped scaffold the Star Tribune Local News Fund (2023–2024) alongside the company’s first head of philanthropic partnerships — donor infrastructure built inside a for-profit newsroom
- Part of the team that rebranded to Minnesota Star Tribune and rewrote the mission, vision, and values
- Helped grow the newsroom from 200 to 250 journalists in 2014–2015 — the largest newsroom in the Midwest
- Contributed to more than $20M in documented revenue over eight years (2017–2024, across this role and the next) across advertising, sponsorship, special sections, and sponsored content — including $6M in 2021, advertising's best year in sixteen
- Led design and the editorial process on Denied Justice, a 2019 Pulitzer finalist that led to four changes in Minnesota’s sexual-assault laws and the state’s first statewide police policy for sex-crime investigations
- Built the visual system the newsroom used to win the 2021 Pulitzer for Breaking News after moving to the business side
- 55-person team across editorial, design, photo, and data; SND top 3 worldwide
- Commissioned illustration, negotiated archival rights, and directed commemorative coverage that launched the Star Tribune Magazine
- Top winner worldwide (SND) for the better part of a decade; 125+ awards
- LA Press Club Designer of the Year; Angus McDougall Overall Excellence in Editing (POYi, staff)
- Directed visual coverage across breaking news, commemorative, investigative, and Olympic events
- Part of the newsroom for three Pulitzer Prizes: Explanatory Reporting (2009), Public Service (2011) and Feature Photography (2011)
- Sixteen years across five Midwest newsrooms — reporting and visual journalism. The foundation for the senior work that followed at the Los Angeles Times and Star Tribune.
volunteer & community
- Community member, District Technology Advisory Committee — South Washington County Schools (ISD 833) (2026–Present) — appointed to help implement the district’s Responsible Use of AI policy
- Advisory Board Member — Public Alliance of Professional Journalists (PAPJ), March 2026–Present. Journalism credentialing standards; developing papj.org in partnership with the founder.
- Mentor — ADPList (global design and product mentorship community)
- President, Board — East Ridge Athletic Association Basketball (2017–2019) — 14-member volunteer board serving ~500 players; rewrote bylaws; research-based fee restructuring with full cost transparency to families (~$20K in new annual program revenue)
- Director of Player Development & Boys’ Traveling Coordinator — East Ridge Athletic Association (2020–2022) — third board role; previously served as president
- Youth Basketball Head Coach — East Ridge Athletic Association (2014–Present) · Minnesota Heat Hoops 16U (2015–2024); Trusted Coaches certified (background check, concussion protocol, youth safety)
- Vice President, Board — East Ridge Robotics Foundation, 501(c)(3), Woodbury, MN — fundraising, sponsor relations, program communications
- Volunteer — East Ridge High School Trap Shooting Team, Woodbury, MN
- Pet Therapy Volunteer — licensed animal-therapy team, Pet Partners; weekly visits with certified therapy dog Jordy
education
B.S., Journalism & Mass Communication — Kansas State University. J-School Ambassador; K-State Collegian.
A.A. — Hutchinson Community College. HCC Collegian.
Executive Certificate, Customer Experience — Minnesota State University Mankato
Executive Training — Poynter Institute · Yale University · Leiden University
what colleagues say
“A forceful agent for change. Congenial, smart, diplomatic but also inspiring.” — Chris Welsch, Microsoft Communications
“He's clear on what he needs from me, but flexible in how I deliver it. He stands up for his artists and creates lasting loyal relationships.” — Robert Carter, illustrator
“He made us better.” — Los Angeles Times
Full recommendations and references available upon request.