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Greg Rosner, founder of PitchKitchen

The Fractional Operator's Working Group

Claude Training for Fractional Executives

A weekly working group for fractional CMOs, CROs, CFOs, and COOs who use Claude across their clients and want to get a hell of a lot more out of it.

You're a fractional executive. You run 3, 5, maybe 8 clients. Every one needs something different. Every one thinks they're your only client.

You're using Claude. Maybe ChatGPT too. It helps. But you know there's a version of this where Claude isn't just answering questions, it's actually doing the work. Drafting the board memo. Loading the client's voice. Holding the strategic context so you don't have to.

You haven't built that yet. Most fractionals haven't. Not because they're behind, because nobody's shown them how.

I run a small group of fractional operators who are figuring this out together. Once a week, 75 minutes. I open with what I've built. Then we pass the mic. Real client problems, real Claude setups, real working sessions. No theory.

Who this is for

  • Fractional executives running multiple B2B clients.
  • Already using Claude or ChatGPT in your work.
  • Tired of figuring it out alone.

Who this is NOT for

  • People who want a beginner course on AI.
  • People who want certifications or curriculum.
  • People who want to watch, not show up.

What you get

  • Weekly live session.75 minutes. Recorded if you can't make it.
  • Slack community of fractional operators between sessions.
  • Template library that grows every week. Real Claude Projects, Custom GPTs, prompts, agents.
  • Direct access to me in Slack between sessions.

The 12 skills we work on

Each one is a piece of scar tissue from my own work. I'll write up each in detail and we'll work through them in sessions. The point isn't the list. The point is what happens when a room of fractional operators starts building on top of it together.

Paper-collage illustration for: Ask AI First
01

Ask AI First

Before you Google it, before you ping a peer, before you book a course. The first move on any new problem is AI. It changes how fast you find the shape of the answer.

Paper-collage illustration for: Skepticism by default
02

Skepticism by default

AI hallucinates. AI drifts. Verify everything that matters. The fractionals who get burned are the ones who skip this step once.

Paper-collage illustration for: Context is everything
03

Context is everything

A fraction of the context produces a fraction of the value. The setup work isn't overhead. It's the work.

Paper-collage illustration for: Always ask for clarifying questions and rationale
04

Always ask for clarifying questions and rationale

Don't accept the first draft. Ask Claude what it didn't know before answering and why it chose the structure it chose. The follow-up is where the real value lives.

Paper-collage illustration for: Lead with the goal
05

Lead with the goal

Stop describing what you want to write. Tell Claude what you're trying to achieve and ask what it needs from you to get there.

Paper-collage illustration for: Treat AI like a new hire
06

Treat AI like a new hire

Daily feedback. Constant coaching. Ongoing management. You wouldn't expect a brand-new VP to nail it on day one with no context. Same rules apply.

Paper-collage illustration for: Clone your own thinking
07

Clone your own thinking

Build a collaboration partner that thinks like you, not a replacement that thinks for you. The output is sharper. The work is still yours.

Paper-collage illustration for: Build AI feedback loops
08

Build AI feedback loops

One AI drafts. Another grades. A third checks for quality. The loops are how you get from rough to ready without burning a full hour.

Paper-collage illustration for: Document what you repeat
09

Document what you repeat

Any process you do three times a week is a process AI should be doing. Write it down once. Hand it over. Get your Tuesday back.

Paper-collage illustration for: Productive with AI agents
10

Productive with AI agents

One agent isn't the ceiling. Multi-agent orchestration is where the next step-change lives. The fractionals figuring this out are billing the same and shipping triple.

Paper-collage illustration for: Cross the chasm
11

Cross the chasm

Connect AI to your actual tools. Gmail. Drive. Canva. Airtable. Otherwise AI ships ideas, not work. Crossing the chasm is the difference.

Paper-collage illustration for: Amplify what you already do
12

Amplify what you already do

Stop asking what to build with AI. Start asking how AI can amplify what you already do well. The shift in framing changes everything downstream.

Hat tip to Sabrina Romanov, whose list of AI working principles got me building the fractional operator version of this.

Who I am

Greg Rosner, founder of PitchKitchen.

60 years old. Four kids, youngest still in diapers.

PitchKitchen is a 7-figure consultancy. Over $1M in revenue. Run solo, no team. Open Kitchen is the operating model that makes it possible.

I run 3 to 7 client engagements at a time. Every client has named AI agents trained on their strategic narrative and voice. Those agents spin up websites, landing pages, sales enablement... the deliverables a marketing agency used to charge $50K for and take 90 days to ship.

I have a mission command center of seven full-time AI agents running 24/7. They have names: Tara, Sara, June, Bob, Spike, Gary, and Cleo. I built the whole thing myself, in a day, without knowing how to code.

Open Kitchen is built on a thesis. AI has collapsed the deliverable layer of marketing. The thinking still matters. The HTML doesn't.

I've got 300+ CEOs of work behind me. Scars from trying to build my own version of Claude (security nightmare, burns tokens, has to be babysat). I crossed the chasm and came back with the map.

I'm not an AI guru. I'm an operator who built the thing and wants to show other operators how to build their own version.

Greg Rosner, seated portrait
Greg Rosner, full body

Why I'm doing this

I'm doing this for two reasons. One is the pull. One is the warning.

The pull. I've seen what's possible on the other side of the chasm. Running a practice that used to require a team of 10 with 7-figure overhead, running it solo with agents. That's not theoretical. That's my day. Other operators deserve to see this.

The warning. Fractional executives who don't get into the messy middle of working with AI are going to get left behind. Companies are going to start expecting AI-leveraged operators in the next 12 to 18 months. The fractionals who can't show up with that leverage are going to lose engagements to the ones who can.

I'm part Pied Piper, part Chicken Little on this. I don't know which one I am on any given day. Both feel true.

I'm building this group because I want other fractionals and operators in the room. Not as students. As peers who get into the mess together and figure out what the next version of this work looks like.

Greg Rosner at sunset
Greg with his wife Polina in Rome
With my wife Polina. The reason any of this matters.

Charter pricing

$50/month for the first 25 members. Locked for life.

Standard price is $100/month once charter slots fill. Cancel anytime. No annual lock-in. No tiers. Just one membership.

Apply for charter membership →

Each application gets a quick yes/no from me within 24 hours. If it's a fit, I'll send a Stripe link with charter pricing locked in.

Fractional operators figuring out AI together. That's the whole thing.