Derek Simmons

Derek Simmons

Writer, filmmaker, builder

Woodbury, MN

email linkedin github orcid résumé (pdf)

summary

Thirty years of writing, editing and building teams in newsrooms, then an independent practice since late 2024. I was the first Chief Creative Officer / VP in the Star Tribune’s 150-year history, led a 55-person cross-platform team, and ran Advertising Policy & Standards reporting to the Publisher and General Counsel. Since late 2024 I have made and shipped work with AI in the production chair: a short film, songs on streaming services, a published essay series, a conversational agent with written guardrails, and a training product with paying clients. This page is the long version. The one-page résumé is the download above.

experience

Founder & Principal Nov 2024 – Present
CW Strategies LLC, Woodbury, MN
  • Directed and released lightning/bug, a short film made entirely from a computer terminal (Mother’s Day 2026)
  • Wrote and released three songs to Spotify and other services, from lyric to master, cover art and distribution, through a release pipeline I built
  • Edit Being Claude, a published series of 40+ essays on human-AI collaboration under an AI byline, with automated voice and fact checks before anything publishes
  • Built Coach D, a basketball training product with AI coaching and paying clients, with written boundaries for medical, mental-health and child-safety questions
  • Write and maintain the guardrails for CW’s Porch, the conversational agent on this site: what it will not make up, where it hands off (medical and legal questions go to a doctor or a lawyer), how it handles political topics, and what it will not say about the people behind it. Every fix is a commit and pull request in Git
  • Built The Standard, an AI knowledge-management system in production since early 2025 across a dozen projects: a governing document for each project, session records, and automated gates that block work that violates documented standards
  • Built Option D, a model-agnostic coaching SDK across nine providers, and used it to run scored evaluations across models
  • Built papj.org for the Public Alliance of Professional Journalists: the site, a credentialing flow, and the Press Box, an agent that teaches journalism standards to the public
  • Built Notice MN, a four-language SMS civic-information tool for Minnesota
  • Strategy retainer with a regional newsroom in the Pacific Northwest (Sept 2025 – Apr 2026): search and discovery (SEO, GEO, AEO), audience strategy, newsletter platform migration, paid-content systems, analytics framework. Began with an audit and one finding: readers searched the city’s name, not the paper’s
  • Red-team testing through HackerOne, with a submitted report
  • Published a working paper on who gets paid when AI learns (see Research)
Chief Creative Officer & Vice President Dec 2013 – Oct 2024
Star Tribune Media Company, Minneapolis, MN · Assistant Managing Editor, Visuals (2013) · first Chief Creative Officer / VP in the company’s 150 years, a role I proposed (2017) · Executive Director, New Products & Digital Strategy (2022)
  • Supervised a 55-person cross-platform team of designers, developers, videographers, photographers and data journalists, responsible for creative across a 1,000-employee company; hired 50 people in two years
  • Helped grow the newsroom from 200 to 250 journalists in 2014–2015, the largest newsroom in the Midwest
  • 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, where federal and state law conflict; ran contract and policy reviews with internal and outside counsel; negotiated content-vendor agreements
  • Contributed to more than $20M in documented revenue over eight years (2017–2024) across advertising, sponsorship, special sections and sponsored content, including $6M in 2021, advertising’s best year in sixteen
  • Built a sports betting content platform and a paid content platform; shipped earned-revenue product on a recurring cycle with the product team, from scoping through post-launch, informed by A/B tests
  • Helped launch an entertainment franchise with a $1M sponsor and worked directly with the sponsor on the creative
  • 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 Prize for Breaking News, after moving to the business side
  • Directed documentary-style video, podcasts, interactive storytelling and VR, plus audience engagement franchises; planned and staffed live-event coverage, including the company’s own events
  • Twenty years on the outdoors coverage across both tenures; art directed and designed Minnesota State of Wonders (2016)
  • Commissioned illustration, negotiated archival rights, and directed commemorative coverage that launched the Star Tribune Magazine
  • Managed the team that built and maintained StribNet, the company intranet; built the Star Tribune’s social media brand, including comment moderation and reader response
  • Science and Health section: health storytelling and reader health challenges
  • AI champion for sales, advertising and marketing; senior leadership team
  • Helped scaffold the Star Tribune Local News Fund (2023–2024) with the company’s first head of philanthropic partnerships: donor and stakeholder infrastructure inside a for-profit newsroom
  • Part of the team that rebranded the company as the Minnesota Star Tribune and rewrote the mission, vision and values
  • SND top 3 worldwide
Deputy Design Director Mar 2007 – Dec 2013
Los Angeles Times, Los Angeles, CA
  • Directed visual coverage of the Olympics, Oscars, Super Bowls and breaking news, from the California wildfires to the election of Barack Obama
  • #1 worldwide in news design (Society for News Design) for the better part of a decade; 125+ awards
  • LA Press Club Designer of the Year; Angus McDougall Overall Excellence in Editing (POYi, staff)
  • Part of the newsroom for three Pulitzer Prizes: Explanatory Reporting (2009), Public Service (2011) and Feature Photography (2011)
News Design, Multiple Roles 1998 – 2007
Star Tribune, Minneapolis, MN
  • Started as a sports graphic artist; senior design roles across print and early digital
Earlier roles 1991 – 1998
Kansas City Star · Associated Press · Wichita Eagle · Hutchinson News
  • Reporting and visual journalism across Midwest newsrooms

research

boards & community

  • Vice President, Board — East Ridge Robotics Foundation, 501(c)(3), Woodbury, MN: fundraising, sponsor relations, program communications
  • Community member, District Technology Advisory Committee — South Washington County Schools (ISD 833), 2026–Present: helping implement the district’s Responsible Use of AI policy
  • Advisory Board — Public Alliance of Professional Journalists, 2025–Present: built papj.org; verification and credentialing standards
  • Mentor — ADPList, a design and product mentorship community
  • Advisor — Ruff Start Rescue, 2023–Present
  • Licensed animal-therapy team — Pet Partners, 2023–Present: weekly senior-care visits with certified therapy dog Jordy
  • President, Basketball Board — East Ridge Athletic Association, 2017–2019: 14-member volunteer board, about 500 players; rewrote the bylaws; fee restructuring with full cost transparency to families (about $20K in new annual program revenue). Director of Player Development and boys’ traveling coordinator, 2020–2022
  • Youth basketball head coach — East Ridge Athletic Association, 2014–Present; Minnesota Heat Hoops 16U, 2015–2024; AAU for more than a decade; Trusted Coaches certified (background check, concussion protocol, youth safety)
  • Volunteer — East Ridge High School trap shooting team; range safety officer, Oakdale Gun Club, 2026

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

Python — Kaggle Learn, 2026

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.