Derek Simmons
Thirty years in newsrooms. Now building with AI.
Woodbury, MN
summary
Thirty years in newsrooms — first Chief Creative Officer/VP at the Star Tribune, where I helped grow the newsroom from 200 to 250 journalists in 2014–2015 and led the team that generated $20M in revenue during the 2020–2022 pandemic. Built the 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). 1,000+ career awards across local, national, and international competitions. Since November 2024, an AI-native creative practice from Woodbury, Minnesota — built claudewill.io, Hancock, Coach D, Battle o' Brackets; directed lightning/bug; author of Being Claude (an ongoing series) with the book Claude Will. forthcoming June 28, 2026.
core competencies
experience
- Cascadia Media Company (Bellingham, WA) — $10K/month 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
- Designed and built Hancock — autonomous AI storyteller publishing weekly with no human-in-the-loop authoring
- Built Coach D — AI coaching platform with 157 drills, cloned voice, basketball training methodology
- 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; book Claude Will. forthcoming June 28, 2026
- Served as newsroom AI champion; senior leadership team
- 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
- Led the team that generated $20M in revenue during the 2020–2022 pandemic — the largest contemporary economic disruption on record
- Built the visual storytelling process for five investigative series — five legislative outcomes, including a Pulitzer finalist that changed four laws
- 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 two Pulitzer Prize-winning investigations
- 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
- 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)
- Vice President — East Ridge High School Robotics Booster Club, Woodbury, MN
- Volunteer — East Ridge High School Trap Shooting Team, Woodbury, MN
- Pet Therapy Volunteer — with Jordy
- Youth Sports Training & Coaching — local, volunteer (multi-sport)
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.