GTM2026 · AI for Fractionals · October 1, New York
AI for a business of one.
Three things I stopped doing by hand, and what replaced them. The videos, the prompts that ran, and a way to start tonight.
Presented with Neil Weitzman and John Williams at Pavilion GTM2026.
The one idea
Teach it once. Reuse it forever.
I run a fractional CMO practice, which is a fancy way of saying I am a marketing department of one for several companies at once. A year ago that meant carrying every client's checklist around in my head. Now I have a command center: a workspace that knows my clients, my voice, my tools, and my rules. The magic word is skills.
The unit
A skill
A document that teaches the AI how you do one specific thing. How you write. How you onboard a client. What your triage rules are. I have about 40 of them.
The split
Chat thinks. Cowork does.
A single chat is great for a draft or a gut check. If the task touches files, tools, or repetition, it belongs in the doing layer. Claude Cowork is my doing layer.
The stack
Connected, not local
Claude Cowork plus the tools I already pay for: Granola, HubSpot, Motion, WordPress, email, calendar. John runs local models for privacy and cost. I run connected tools for reach. Both work.
01
Judgment on file
Write the rulebook once.
I run customer communication for a client's pilot program. I am not in most of those conversations, and nobody reads a 12-page rulebook. So I wrote how I answer as a skill. Now anyone who touches a customer inherits my judgment, including the part where the right answer is "not yet."
85 seconds. Fictional customer. Real skill.
What I typed
Beat 1: messy call notes, no instructions
Call with Dana at Ridgeline Pharmacy went well. She's on PioneerRX. Main worry is her two techs thinking this replaces them. She wants to know how fast we can be up and running. Told her I'd send something in writing.
Beat 2: two landmines in one casual sentence
One more thing I forgot from that call: she asked if PAT could handle prior auths, and she mentioned she's buying a second store in Q1.
What to watch
- 01Messy notes go in.
- 02The skill loads on its own.
- 03Risky items get flagged.
Your starting move
Pick one type of customer question you answer over and over. Write down ten rules for how you answer it, including the questions you never answer in writing and who gets told when they come up. Paste those rules into a Claude project or a Cowork skill. Then hand it your next set of messy call notes and read what comes back.
02
Websites by asking
One sentence replaces 25 minutes.
I manage my own WordPress site and three client sites. I used to dread small edits. Now there is a skill per site. It knows the page IDs, how every section is built, and the gotchas. Mine has a section on the exact way I broke the site once, so it never does that again.
Before
- find the page
- find the block
- copy the pattern
- fix desktop and mobile
Now
- ask once
- it finds the page
- drafts the change
- shows the diff
45 seconds. Every edit still gets my approval before it publishes.
What I typed
Add my October 1 GTM2026 talk, AI for Fractionals, to the speaking page on crysblack.com.
What to watch
- 01Plain-English request.
- 02It finds the right page.
- 03It shows exactly what will publish.
The skill holds the page IDs, the pattern for a speaking entry, the two ways I have broken the site before, and the rule that nothing publishes until I say yes.
Your starting move
Write a one-page document about your website. Where things live, how a section is built, what you never want changed, and the rule that you approve every edit before it goes live. That document is the skill. Then ask for one small edit and watch it show you the change before it publishes.
03
Events that find me
The events list writes itself.
Every week I post a networking roundup to the Colorado channel in Fractionals United Slack. It used to take me an hour on Sunday. Now a scheduled task runs Sunday at 5 and hands me the post formatted the way I write it. I check the links and paste. Ten minutes.
STEP 01
Looks two weeks out
STEP 02
Applies my networking rules
STEP 03
Returns only what's worth attention
Sources: startup groups, AI communities, chambers, my own calendar.
60 seconds. The instructions are long on purpose. The rules are the asset.
The rules, written once
- The whole state, not just the Front Range
- Would a fractional or a founder go here to make a business connection? If not, leave it off.
- No Young Professionals mixers. I flagged that twice. Now it is a rule.
- A short list that fits beats a padded one.
- Confirm every date on the event page itself. Check every link. If it cannot be confirmed, drop it.
- No emojis. Ever.
What to watch
- 01Scheduled task starts.
- 02Sources get checked.
- 03Events are scored and verified.
Read the full task instructions
[Scheduled task: weekly-co-networking-events. Runs Sundays at 5:00pm America/Denver.]
You are preparing Crys Black's weekly networking-events roundup. Crys posts this every week to the Fractionals United "Colorado" Slack channel. Produce a finished, copy-paste-ready draft for Crys to review and paste herself. Do not attempt to post to Slack.
GOAL: Find networking and community events happening across the whole state of Colorado over the next two weeks, weighted toward startup / founder / tech / AI ecosystem events, because those companies are the most likely to hire fractional executive leadership. Cover the entire state: Colorado Springs, Fort Collins, Loveland, Longmont, Golden, Durango, Grand Junction, Pueblo, and anywhere else you find them.
AUDIENCE FIT FILTER (apply before including any event): The reader is either a fellow fractional executive looking to network with peers, or a founder who might need fractional support. INCLUDE startup and founder meetups, pitch nights, tech and AI meetups, founder socials, chamber business mixers, women-in-business and women-in-tech events, industry conferences, and professional networking aimed at business owners or company leadership. EXCLUDE hobbyist or consumer gatherings with no business networking angle (makerspace open houses, ribbon-cuttings, cause-branded mixers, festivals). EXCLUDE anything branded "Young Professionals" or "Rising Professionals"; Crys has flagged these twice as skewing too junior. When in doubt ask: would a fractional exec or a founder go here specifically to make a business connection? If the answer is no, leave it off. A shorter, well-fit list beats a padded one.
STEP 1. Establish the date window. Run `date`. "This week" is today through this coming Sunday. "Next week" is the following Monday through Sunday. Never list events that have already passed.
STEP 2. Read last week's handoff doc in Google Drive ("Fractionals Networking Roundup, Handoff, auto-maintained"). It carries the prior run's "Next week" list and standing exclusions. Hold onto it for Step 5.
STEP 3. Ask Crys about Fractionals United virtual meetings first. They are not listed publicly. Leave a placeholder bullet so they slot in when she replies. Do not block the draft waiting.
STEP 4. Gather events from: the RMAIIG calendar via the Google Calendar connector (AI events statewide); coloradostartups.org/event-calendar; siliconflatirons.org/events; Meetup via web search (Meetup's discovery pages are JavaScript-rendered and return empty shells, so search instead); aggregators such as TechMeetups, Eventbrite, Wyrl, Revel, and the Colorado Startups Luma page; and chamber-of-commerce calendars in the smaller cities, with the audience fit filter applied. If a source is blocked, note it and move on.
STEP 5. Filter and select. Keep recurring staples (1 Million Cups, Boulder Open Coffee Club, PitchBoulder, AI and tech meetups, startup happy hours, pitch nights) plus one-off conferences and mixers. Spread geographically. Drop purely virtual webinars unless they are clearly valuable networking. Aim for roughly 12 to 18 events per week when available, but never pad. Cross-check against the handoff doc: anything promised for "next week" last time that your fresh search missed gets re-verified live and included if it still checks out.
STEP 6. Cross-reference Crys's primary Google Calendar for the same window. If she created the event, tag it "(I'm hosting)". If she is attending, tag it "(I'm attending)". Match on topic and date, not exact title.
STEP 7. Format the draft to match this template exactly:
Hi Colorado fractionals! Hope everyone is soaking up the sunshine. Here's what I'm seeing this week.
* Tuesday morning in Boulder is the [Boulder Open Coffee Club](url)
* Wednesday morning in Denver is [1 Million Cups](url)
* Thursday evening in Denver is [AI & Product CO's BYOB: Bring Your Own Brain](url) (I'm attending)
Next week:
* Wednesday evening in Boulder is the [AI & Ethics Happy Hour at Rayback Collective](url) (I'm hosting)
Happy networking!
Rules: open with a short, warm one-line greeting in Crys's voice, then "here's what I'm seeing this week." Absolutely no emojis. Two sections, this week then "Next week:". Each bullet is day of week, time of day, city, "is", then the event name as a markdown link. Hyperlink the event name, never leave a raw URL. Close with "Happy networking!"
STEP 8. Verify before delivering. For every event, fetch its actual event page and confirm the date, day, and time match what you are about to publish. Confirm every link resolves. If a date cannot be confirmed on the event page, leave the event out rather than guess.
STEP 9. Update the handoff doc with this run's "Next week" list, a "Last updated" line, and short notes for next run, including standing exclusions.
STEP 10. Deliver the draft as plain text Crys can paste into Slack. Above it, list the date window, the sources used, the event count, and a one-line confirmation that every date and link was verified on its own event page. Below it, list anything you were unsure about so Crys can decide.Your starting move
Pick one list you make every week. The rules you use to decide what goes on it are already in your head. Write them down, including the things you always cut and why. Give the AI the sources, the rules, and the format you post in. Schedule it for the night before you would normally do it by hand.
The caveat
None of this worked on day one.
My first skills were bad. I still catch it doing things wrong, and the skill gets a new rule that same day. It is a system you garden, not a system you install.
01
My first skills were bad.
Every one of them.
02
Feedback made them useful.
Each correction became a rule the same day.
03
This is a system you garden.
Not a system you install.
The slides
The deck from the session.
Twelve slides, including the three demos above. Slides are added here after the session on October 1.
Slides coming after October 1
Before you go
Give it context. Give it feedback. Write down your standards.
Stop treating AI like a vending machine. Treat it like a new hire. A new hire needs context, feedback, and your standards written down. Do that, and it stops being a demo and starts being a system.
Email me the task you resent most.
I will read it and send you my skill template with a starting move written for that task.