cwclaudewill*
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CW Strategies
ai-native coaching for teams
claudewill.io

Your team knows AI matters.
They don't know where to start.

The devil isn't in the details. It's in the approach.

The standard that works

How we work

build

Assess where you are. Identify what's working and what isn't. Build AI workflows and strategic frameworks tailored to your team and your problems.

transfer

Train the team. Document everything. Make the system theirs. The goal is a team that runs the second month with less support than the first.

exit

Leave. A good consultant builds capacity, not dependency. If the work only works when I'm in the room, it doesn't work.

Timeline: A day, a month, a quarter. Billing: Retainer or project-based.

The proof

"Thank god you're a team player, Derek." · "You make us feel less crazy."

Hired for a one-month organizational audit. Six months later, we'd outgrown every scope.

Line item Amount
Contract savings (vendor negotiation) $18,000
New revenue launched (Q1, on pace) $14,000
Costs avoided (UX, PM, art direction, platform strategy) $30,000+
Recurring annual platform savings unlocked $7,000–$18,000
Strategic decisions supported 19
Written deliverables produced 14
Total financial return (Q1) $62,000+
Q1 investment $30,000
Month one ROI: 250–450%. Every phase earned the next. The math isn't close.

The paid content system built during this engagement is modeled to generate $200K annually at scale.

Derek Simmons

30 years in media. Star Tribune, LA Times. First and only Chief Creative Officer and VP in the Star Tribune's 150-year history. $20M generated during a pandemic. Four Pulitzer Prize-winning teams. Kansas State journalism degree. Now building with AI full-time.

30
years in media
$20M+
revenue generated
4
Pulitzer Prize teams
2,000+
AI working sessions
"A forceful agent for change. Congenial, smart, diplomatic but also inspiring."

Two ways in

Fractional Leadership

Embedded strategy

10-20 hours per week. Retainer. I become part of your team — strategy, operations, AI integration, decision support.

  • AI workflow design
  • Platform and vendor strategy
  • Revenue and audience development
  • Organizational coaching
Team Training

Practical AI skills

2-3 sessions for your team. Not theory. Hands-on workflows they'll actually use — research, writing support, document analysis, guardrails.

  • Tool-agnostic (works with what you have)
  • Ethical frameworks included
  • Built for skeptical teams
  • Customized to your newsroom

Both start the same way: a conversation about where you are and where you want to be.

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Let's talk.

Start

Before we talk, a few questions. This isn’t a test. It’s a filter for both of us. Take 10 minutes. Be honest. There are no wrong answers, but vague ones tell me you’re not ready.

Not “what’s your goal.” What are you actually trying to build? A practice? A team capability? A system? Be specific.

What tools have you experimented with? What worked? What didn’t? If “nothing yet,” tell me why now.

Time. Budget. Team buy-in. Technical knowledge. Fear of looking stupid. Overwhelm. What’s yours?

Be concrete. What’s different in your work, your team, your organization if this engagement works?

How did you find me? What made you fill this out instead of closing the tab?

Select all that apply.

Context matters. Situation, timeline, constraints. Whatever helps.

I’ll review your answers within 48 hours. If there’s a fit, I’ll reach out. If not, I’ll tell you that too. No ghosting.