The AI SMB Toolkit
Four documents that turn AI curiosity into a working plan.
A practical kit for executives and operators at companies with 25 to 150 employees — covering platform selection, employee discovery, vertical-specific workflows, and self-serve course building.
Who this is for
Built for the people who have to make AI real inside their organization.
Not for data scientists or enterprise IT departments. For the operator who needs to move, the executive who needs to decide, and the HR leader who needs to bring their people along.
CEOs and COOs
You are being asked what AI the company already has, what it should buy next, and how to govern it. This kit gives you the framework and the documents to answer all three.
HR and People Leaders
You need to surface what employees actually think about AI before rolling it out — and then build training that feels relevant to your culture, not copied from a template.
Operations and Department Heads
You manage workflows across finance, sales, marketing, and customer operations. The prompt cookbook puts working AI automations in your hands without requiring engineering support.
Consultants and Advisors
You serve SMB clients who are asking AI questions you need to answer with authority. These documents are built to be client-ready — hand them over or use them as the backbone of an engagement.
What’s inside
Four documents. One coherent system.
Each deliverable is a standalone Word document you can use immediately — customize the tables, add your company name, fill in your tools. Together they cover the full arc from inventory to activation.
Answers the question every CEO asks first: “What AI do we already have in our tools that we are not using or know about?” Then answers the question that follows: when you do need to buy a commercial AI platform, how do you choose the right one for your ecosystem, your compliance requirements, and your team’s actual work?
Includes a five-phase inventory process, a commercial platform decision framework comparing Claude, Microsoft 365 Copilot, and Gemini for Workspace, and a deep-dive compliance section for regulated industries.
- Master technology inventory table with AI feature discovery columns
- Five-factor commercial AI platform selection framework
- Side-by-side platform profiles: Claude, Copilot, Gemini — pricing, compliance features, ecosystem fit, and honest trade-offs
- Four-question decision guide to route your organization to the right starting platform
- Three non-negotiable controls for regulated-industry AI deployment (data retention, scoped access, audit logging)
- Vertical-specific compliance tables for financial services, manufacturing, SaaS, agencies, and hospitality
- AI Registry template — a living record of every AI capability in production at your organization
The single most common reason AI projects stall is resistance that leadership did not see coming. This survey gives employees a structured, safe way to share their real concerns, ideas, and readiness — before the rollout, not after. HR leaders can customize every question to match their culture and tone.
Each of the 15 questions includes an Intent note (what you are trying to learn and why it matters) and a Tone Customization note (how to reword the question for formal, casual, or high-trust cultures).
- 15 questions across five themes: awareness, pain points, concerns, ideas, and governance preferences
- Intent and tone customization guidance for every question
- Recommended deployment methods: anonymous pulse survey, Google Forms, facilitated team discussion
- Five-step analysis framework to translate results into a use-case backlog and training design input
- Guidance on the questions most likely to surface Shadow AI usage already happening inside your organization
The fastest path from “we should do something with AI” to “AI is doing something useful today.” Each prompt is formatted for immediate use in Claude, ChatGPT, or any frontier model — copy, replace the bracketed variables with your specifics, and run. Every prompt includes a usage note explaining when and how to apply it and what to watch for.
Covers Finance, Sales, Marketing, Operations, and Product/Customer Success for each of the five verticals below. Closes with a workflow automation architecture table that pairs each vertical to its recommended automation stack and highest-ROI first workflow.
- RFQ response generation, SOP writing, and supplier risk assessment for manufacturing
- Client portfolio narratives, prospect meeting prep, and coverage gap analysis for financial services
- SaaS metrics commentary, sales call debriefs, user story generation, and QBR preparation
- Agency profitability analysis, creative brief generation, and client report narratives
- Flash report writing, event proposals, review response drafting, and menu engineering analysis for hospitality
Companies that adopt AI best are the ones that train their own people in their own context. This document gives any organization a master prompt — built on Anthropic’s published prompting techniques — that generates a complete, Teachable-ready AI training course from a short intake brief. No instructional design experience required.
One run of the master prompt produces a full course package including marketing copy, lesson scripts with worked AI examples, exercises, quizzes, a capstone project, a drip email sequence, and SEO metadata. The document includes pre-filled intake examples for each of the five verticals and a ten-course library to build from.
- Course intake brief template — four XML-tagged inputs that replace a full instructional design brief
- Master prompt: three-phase architecture (plan, build, self-check) aligned to Anthropic’s prompting guidance
- Pre-filled vertical intake examples for all five industries — copy, adjust, run
- Step-by-step Teachable deployment workflow — from Markdown output to published course
- Ten-course library: two ready-to-run course concepts per vertical, each with topic and learner outcome
- Pre-publish quality checklist with owner and pass/fail fields
For regulated industries
Shadow AI is your most immediate compliance exposure.
Staff using personal AI accounts for work involving client or patient data is the primary AI compliance failure mode across financial services, healthcare, and legal. Document 01 addresses this directly.
What Doc 01 covers for regulated SMBs
The kit includes enterprise-tier compliance specifications for Claude, Microsoft 365 Copilot, and Gemini for Workspace — verified against current vendor documentation as of mid-2026. For financial services, it covers the three non-negotiable controls the SEC, FINRA, and Regulation S-P demand before any client data touches an AI tool: contractually protected data handling, scoped access controls, and audit-ready logging of AI-generated content that relates to regulated business activity.
The governance framing reflects 27 years of technology and compliance leadership experience in financial services, including direct work with RIAs, broker-dealers, and their compliance teams on technology adoption under SEC Rule 204-2, FINRA Rules 3110 and 4511, and Regulation Best Interest. This is practitioner guidance, not a legal opinion — your compliance counsel should review any AI policy before deployment.
About the author
Pricing
Start where it makes sense for you.
The full kit is the primary offer — four documents, one system, one price. The Prompt Cookbook is available separately as an entry point for teams who want to move immediately on a single vertical.
Entry point
The AI Prompt Cookbook
30+ production-ready prompts across five verticals and five departments. Copy, customize the variables, run immediately in Claude or any frontier AI model. The fastest path from “we should do AI” to “AI is doing something useful today.”
One-time · Instant download · Word document
- ✓ 30+ prompts: Finance, Sales, Marketing, Operations, Customer Success
- ✓ All five verticals: Manufacturing, Financial Services, SaaS, Agencies, Hospitality
- ✓ Usage notes and workflow automation architecture table
- – Platform selection and compliance guide
- – HR discovery survey
- – Course builder prompt system
Included in the full kit below · Save $41 by buying the bundle
Full toolkit
The AI SMB Toolkit — All Four Documents
The complete operating system for AI adoption at a 25–150 person company. Platform selection, employee discovery, vertical workflows, and self-serve course building — in four customizable Word documents.
One-time · Instant download · Four Word documents
- ✓ Doc 01: AI Stack Inventory & Platform Selection Guide
- ✓ Doc 02: HR AI Discovery Survey — 15 questions with tone guidance
- ✓ Doc 03: Prompt Cookbook — all five verticals
- ✓ Doc 04: Self-Serve Course Builder — Teachable-ready prompt system
- ✓ Compliance guidance for regulated industries (financial services, healthcare)
- ✓ AI Registry template and activation checklist
Includes the Prompt Cookbook · $41 less than buying separately
The AI SMB Toolkit
Four documents. Five verticals. One coherent plan for AI in your organization.
Download all four Word documents. Customize for your company. Use immediately — no technical setup, no subscriptions, no consultants required.
Get the full toolkit — $197One-time purchase · Instant download · All four documents
Just need the prompts? Get the Prompt Cookbook for $69.