Trent Gillespie
May 20, 2026
AI just crossed another threshold for business adoption.
On May 13, Anthropic launched Claude for Small Business inside Claude Cowork — a set of prebuilt workflow templates that put AI to work inside the tools most small and mid-size businesses already run on: QuickBooks, HubSpot, PayPal, Canva, DocuSign, Google Workspace, and Microsoft 365.
The important part isn't the new workflows. It's the shift.
AI implementation used to require builders. Increasingly, it requires operators.
For the past three years, I've said from stages that AI would become the new operating system for business. Not another app. Not another dashboard. A layer sitting between you and your tools, handling the recurring work currently eating your evenings and weekends.
That's what I think this launch represents.
The workflows handle operational tasks like payroll prep, monthly close, invoice follow-ups, lead triage, campaign execution, and customer summaries. Every action gets queued for approval before anything sends, posts, or pays. The AI does the work. The human stays in control.
And this isn't unique to Claude. OpenAI, Microsoft, and Google are all moving toward the same destination: AI connected directly to your operational systems. Anthropic just arrived first with the most complete SMB package.
It’s worth understanding why: the workflows are template instructions for the AI to follow. No proprietary technology locks them to Claude. ChatGPT's Agents can run similar logic. Microsoft's Cowork is actually built on Claude Cowork. If you're on a different platform, this still applies to you. These workflows are coming everywhere, fast.
This is the most accessible AI has ever been for small and mid-size businesses. No developer required. No custom automation stack. No consulting engagement just to get started.
But accessible doesn't mean automatic. That's the part most businesses are about to learn.
I connected Claude SMB to my QuickBooks and HubSpot, and within minutes it generated a quarterly business review using live financial and pipeline data. Something I never would have built manually because the setup time alone made it irrational. Now it just exists. Regularly.
That's the bigger shift hiding underneath all this.
AI isn't just automating existing work. It's making previously unjustifiable work suddenly worth doing. Most operational tasks businesses know would help — weekly reporting, CRM cleanup, campaign summaries, pipeline reviews — never happen because the administrative overhead outweighs the value. That equation is changing fast.
I asked Claude to clean up my CRM. Not recommend changes. Make them. It flagged stale deals, identified duplicates, filled missing fields, and queued the updates for my review.
Done.
A realtor managing their own pipeline, marketing, contracts, and follow-up doesn't have an operations team behind them. That's exactly who these systems are built for. The follow-up emails after an open house, the overdue invoice reminder, the campaign reporting nobody has time to assemble — queued, drafted, ready for approval.
The mistake most businesses are about to make is trying to implement everything at once.
Anthropic launched the SMB plug-in with 25 workflows across six categories: daily briefings, financial management, sales and CRM, marketing, customer service, and legal and hiring. Here’s an infographic I made to show them.
Most businesses should ignore almost all of them at the start.
Start with one. Not the most impressive one. The most painful recurring one. For some businesses that's invoice follow-ups. For others it's lead triage, monthly close, or cash flow visibility. The best early use cases are the painfully boring operational jobs that quietly consume hours every week.
That's where this starts to compound.
If you're on ChatGPT, Copilot, or Gemini, the workflow library is still the map. See which workflows might make sense for you. Then copy them.
Through our new OpenAI SMB Channel Partnership, we've negotiated 20% back on new ChatGPT Business licenses for six months. If you're just getting started or looking to add seats, that adds up quickly. Reply and we'll get you set up. 5 license minimum. Terms apply.
The prebuilt workflows are not finished products. They're starting points. They need your context, your standards, your tone, your edge cases. Brief it like you're onboarding a strong new hire.
"Pull this week's overdue invoices and draft follow-ups in the same tone as the last three I sent" will outperform "follow up on invoices" every time.
Someone needs to set this up and own it continuously. If you have a team, assign someone to develop and improve your workflows as an ongoing function, not a one-time project. If you're running solo, this is one of the highest-leverage investments of time you can make.
One working workflow becomes two. Two becomes five. Five becomes operational momentum.
On Claude: Open Claude. Go to Cowork, then Customize, then Browse Plugins. Find Anthropic, select Small Business, and install it. Type "smb-onboarding" and it walks you through the rest. Connect your tools, pick your first workflow, give it your context, and run it.
On ChatGPT: The workflow instructions that power the Claude plugin are mostly transferable. Install it in Claude, choose the ones relevant to your business and ask Claude to rebuild them for ChatGPT, then paste them into an Agent, Skill, or Custom GPT, customize, and connect your tools.
On Microsoft Copilot and Google Gemini: Not yet. Both are limited to their own ecosystems today, and are less functional for this agentic work across systems. They’ll catch up within the next 6 months.
On any platform: Start with one workflow. Get it working. Schedule it. Then pick the next one.
Start with one, not twenty. Pick the recurring task that costs your team the most time. Get it working before you touch anything else.
Treat it as a function, not a project. Someone needs to own workflow development continuously. That's the investment most businesses are still avoiding.
Operational maturity is the new differentiator. Access to AI is no longer the advantage. What you build with it — consistently, deliberately, over time — is.
Hit reply and tell me: what's the one recurring task you'd hand off first if you could?
Trent Gillespie is CEO of Stellis AI and a keynote speaker helping business leaders understand and operationalize AI in their companies. He spent almost nine years leading global innovation efforts at Amazon before leaving to help other companies build the capabilities they need to compete. Book Trent to speak to your group or book a call to discuss using AI within your business.
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