A complete, session-by-session program for HAE's AI Tools for Small Business course — including challenges, perspectives, prompts, demos, tools, and the artifacts each participant ships.
The course has evolved from a Claude Cowork walkthrough into a practical operating-system course for founders, small and medium-sized businesses, and their teams. The strongest insight from across the meetings: SMBs do not need more AI tools — they need a way to reduce tool overload, turn messy business context into usable outputs, and connect AI directly to revenue.
Three forces shaped the new design:
Jack pushed for GTM to be central, not a footnote. Regina insisted every workflow had to tie back to revenue — investor network, academy licensing, sponsor growth. Jamie kept it grounded in adoption reality: don't overload Session 1, make it promotable, and turn the course itself into its own live case study.
The result: a four-session arc that moves Workspace → Strategy → Creative → Distribution, every session producing a real artifact participants leave with.
Pulled from real conversations with Regina, Jamie, and the broader HAE community. Each challenge directly shaped a session.
Notion, Clay, Perplexity, Apollo, Signal, Monday.com, Canva, Gamma, Descript, ChatGPT, Drive, Gmail. Nobody can master ten tools — and each only solves one slice. Data fragments. The "AI stack" becomes another source of complexity.
Regina had 3,200 files across 54 desktop folders. Jamie was hand-rebuilding ChatGPT-generated Word docs into PowerPoint. AI performs poorly when context is scattered — the first AI win is usually organizing what already exists.
Regina was clear: every AI investment has to be justified as a revenue generator, not a productivity perk. Budgets are tight. "Nice-to-have productivity" is not enough.
Jack's feedback to include GTM was important. Founders need help answering: who is the customer, what is the offer, what channel, what message, what sequence to test, what success looks like.
The biggest blocker isn't intelligence — it's knowing how to ask. Regina noted she would never have naturally written prompts like "Score this from 1 to 100" or "What's the fastest, simplest, easiest way to generate revenue from this?"
Jamie's old workflow — ChatGPT → copy/paste → manual PowerPoint cleanup — is a classic SMB pattern. People accept rework as normal. AI helps only when the workflow is redesigned, not patched.
Cowork setup exposed real friction: account switching, plan confusion, connector setup, password issues, Chrome extension hiccups, rate limits, nonprofit pricing questions. Adoption can fail before value is reached.
Each brought a different lens — execution, strategy, adoption — and the syllabus reflects all three.
"AI as a co-worker, not a chatbot."
"Strategic. Revenue-first."
"Operational. Practical. Promotable."
The original draft was tool-led: Cowork, Marketing, Finance. The new arc is outcome-led — driven by Jack's GTM push, Regina's revenue framing, Jamie's emphasis on making it ship.
The new arc speaks the language of small-business outcomes — not software. Finance and operations remain available as bonus material, but the capstone now lives where SMBs actually feel friction: distribution.
AI as a co-worker, not just a chatbot.
The business problem. Small businesses are drowning in files, emails, half-finished docs, and ten unconnected tools. Before AI can help anyone, it needs business context — and most businesses don't have a structured place to give it.
Turn scattered ideas into a clear go-to-market plan.
The business problem. Most founders have a product, service, or program — but struggle to define the target customer, message, channel, and offer with enough sharpness for AI to actually help.
AI can generate lists, but growth depends on relationship quality. Especially for investors, partners, and high-trust sales — the goal is warm intros, credibility, and thoughtful sequencing, not "spray and pray."
Move from idea to finished creative — using the new AI design, video, and prototyping stack.
Before tools: who is the audience, what is the offer, what is the message, what channel, what desired action. The brief drives everything.
Generate campaign concepts, moodboards, visual identity directions, and ad/social creative directions.
Generate landing pages, registration flows, lead capture pages, and dashboard UI from prompts.
Turn static designs into working pages: landing pages, ROI calculators, AI readiness assessments, lead capture forms.
HeyGen for human-facing avatar video, founder messages, and personalized outreach. Hyperframes is the focus for scroll-stopping, visually dynamic short video built for LinkedIn, course promos, webinar promotion, and sales follow-up.
Course module intros, internal training, product explainers, customer onboarding, sales enablement.
Narrative video sequences — problem → tension → transformation → outcome → CTA.
Get the right message to the right people — and keep momentum after the first touch.
The business problem. SMBs often create decent marketing assets but struggle with distribution. They lack a clear list strategy, channel plan, outreach sequence, follow-up process, or engagement system. AI can help — but only if it's pointed at relationships, not volume.
AI helps generate lists and messages, but distribution is not just volume. For high-trust audiences — investors, partners, sponsors, enterprise buyers — the goal is better targeting, warmer intros, higher-quality engagement, and clearer follow-up. Not "spray and pray."
The strongest version of this course is not "AI Tools for Small Business" as a tour. It is AI for Small Business Execution — and the promise is that participants leave with working assets, not just knowledge.
That structure keeps the course practical, reduces overwhelm, and gives HAE a built-in promotional flywheel — every cohort produces real artifacts, real testimonials, and real demand for the next round.