Courses for small and medium businesses

AI, minus the complexity

Live, hands-on AI courses for small-business leaders and their teams. No jargon, no coding — you work on your own tasks and leave with results you can use Monday morning.

76%

of small businesses now use AI

Goldman Sachs 10,000 Small Businesses Voices, 2026

73%

say more training would help them get results from AI

Goldman Sachs 10,000 Small Businesses Voices, 2026

91%

of small businesses using AI say it boosts revenue

Salesforce SMB Trends Report, 2025

10%

of small-business workers have been offered formal AI training

U.S. Chamber of Commerce Foundation, 2026

79%

become regular AI users after 5+ hours of hands-on training

BCG AI at Work, 2025

Most small businesses use AI. Few get real results from it.

76% of small businesses now use AI in some form — but only 14% have it working inside their core operations. That gap is where time and money leak, and closing it takes training, not another tool. Our courses are live and plain-language: you and your team practice on your own real work, and every session ends with something running — a workflow, a policy, or a working AI agent.

The courses

Two tracks. One for the corner office, one for the whole team.

Leaders decide where AI pays off and set the rules. Teams put it to work on the daily grind. Take one course or run the tracks side by side — every session is live, and every session ends with something your business keeps.

For executives

AI Essentials for Business Owners

Owners, partners, and senior managers — no technical background needed

Length
Half day (4 hours)
Format
Live workshop · small leadership cohort
What AI can and can’t do todayThe tools worth knowingSpotting use cases in your operationsJudging results without the hype
You leave with
  • A plain-language map of what today’s AI tools actually do — and what they cost
  • A shortlist of 3–5 use cases matched to your own business, ranked by payoff and effort
  • A one-page brief you can share with your team about where you’re heading
Book this course

Your AI Playbook: Policy, Rollout, Results

Leadership teams ready to move from trying AI to running on it

Length
One day (6 hours)
Format
Live working session with your leadership team
Which data never goes into an AI toolUsage guidelines people followChoosing tools without a consultantMeasuring time saved and return
You leave with
  • A written AI usage policy and data-safety rules your staff can actually follow
  • A 90-day rollout plan with owners and milestones
  • A simple way to measure whether AI is paying off in hours and money
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AI Agents for Decision Makers

Leaders deciding what to automate next

Length
Half day (4 hours)
Format
Live workshop · in person or virtual
Agents in plain termsWhich processes are ready to automateStaying accountable for agent outputWhat agent projects really cost
You leave with
  • A clear grasp of what AI agents are — software that completes multi-step tasks — and where they fail
  • A ranked list of processes in your business worth automating first
  • A build-or-buy decision framework with realistic cost and effort estimates
Book this course

For your team

AI Foundations at Work

Everyone on the team, whatever their role — no experience assumed

Length
Half day (4 hours)
Format
Live team workshop · cohorts of 11–25
How these tools work, without the mathPrompts that get useful answersJudging output: trust, question, fixData safety basics
You leave with
  • Your first real task completed with AI before the session ends
  • A personal prompt kit built for your actual role
  • Clear rules on what’s safe to share with AI tools — and what never is
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AI in Your Daily Workflow

Teams who know the basics — sales, admin, service, finance, marketing

Length
One day (7 hours)
Format
Live hands-on workshop · everyone works on their own job
Role-by-role workflowsTurning a recurring task into an AI routineChaining steps: draft, check, refine, sendQuality control that keeps a human in charge
You leave with
  • 2–3 of your own recurring tasks rebuilt with AI, working before you leave
  • Reusable templates and checklists for your role
  • A realistic estimate of hours saved per week, measured on your own work
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Build Your First AI Agent

Teams who use AI weekly and want routine work handled for them

Length
One day (7 hours)
Format
Live build session with an instructor at your side
What makes a task agent-readyBuilding an agent step by step — no codingConnecting it to tools you already useTesting, guardrails, and human sign-off
You leave with
  • One working agent, built by you, handling a real recurring process — think inbox triage or weekly report prep
  • The skills to adjust and maintain it after the workshop
  • A shortlist of your next two automation projects
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Monthly AI Coaching

Teams that finished a course and want the habits to stick

Length
90 minutes per month, ongoing
Format
Live group coaching · virtual
Fixing workflows that stalledNew tool features worth your timeFresh use cases from businesses like yoursKeeping prompt kits and agents up to date
You leave with
  • One new or improved workflow every session
  • Answers to the questions that piled up since last time
  • Steady progress without pulling anyone off the job for full days
Book this course

Why it sticks

Built the way training research says it works

Your work, not demos

Every exercise runs on your own quotes, inboxes, reports, and schedules. Training sticks when it changes how your Tuesday goes — not when it shows someone else’s slides.

Live, in plain language

Live cohort courses get finished — 64% completion versus about 13% on big self-paced marketplaces. An instructor in the room, no jargon, questions answered as they come up.

One focused day, not a semester

BCG found five or more hours of hands-on training is the threshold where people become regular AI users. Each course clears that bar in a single half or full day.

Follow-up built in

One-off demos fade. Monthly coaching keeps workflows improving, answers the questions that pile up, and turns a good workshop into a lasting habit.

Straight answers

The questions every owner asks first

We’re not a tech company. Is this really for us?

Yes — that’s exactly who these courses are for. 95% of small-business decision makers say they need more AI training (TeamViewer, 2025), and 41% of small-business workers point to a skills gap as a barrier (U.S. Chamber of Commerce Foundation, 2026). Nothing here requires coding or a technical background. You practice on your own real work — quotes, invoices, customer emails, schedules — in plain English, with an instructor in the room.

We don’t know where to start.

You’re in good company: 41% of small-business workers say it’s unclear how AI applies to their specific business (U.S. Chamber of Commerce Foundation, 2026). That’s what the first executive course is for. In half a day we map what AI can genuinely do against how your business actually runs, and you leave with a shortlist of three to five use cases ranked by payoff and effort. Start there; everything else builds on it.

Is our data safe in these tools?

That worry is healthy — and common. Data privacy and security is the top barrier for small businesses still testing AI, cited by 38% (Reimagine Main Street / PayPal, 2025). Every course covers the ground rules: what should never be pasted into a public AI tool, how to set up business accounts so your data isn’t used to train anyone’s models, and which tools meet which standards. The AI Playbook course goes further — your leadership team leaves with a written data-safety policy your staff can follow.

What does this cost in time and money?

Each course is a half day or one day — on purpose. BCG found that five or more hours of hands-on training, with live sessions and coaching, is what turns people into regular AI users: 79% versus 67% for those who got less (BCG, 2025). One focused day clears that bar. On budget: live team AI workshops in this market run $3,000–$12,000 per session for 10–25 people — roughly $200–$1,000 a head (Pertama Partners, 2026), compared with $3,850 for a single seat in MIT Sloan’s online AI program. We price per team session, so your whole team trains for around the cost of sending one or two executives to a business school.

Couldn’t we just learn this from YouTube?

You can get some distance that way — 57% of small businesses name YouTube and social media as their main AI training source (Thryv, 2026). The problem is follow-through. Self-paced courses finish at 48%, big course marketplaces average about 13%, while live cohort courses finish at 64% — and well-run cohorts with coaching reach 85–96% (Ruzuku, 2026). BCG’s research names live instruction, in-person sessions, and coaching as the parts of training that actually work (BCG, 2025). Videos explain AI. A workshop changes how your Tuesday goes.

Will this end with AI replacing my team?

The evidence points the other way. 87% of small-business owners say AI supports their employees rather than replacing them (Goldman Sachs, 2026), and 82% of small businesses using AI grew their workforce over the past year (U.S. Chamber of Commerce, 2025). The point of training is to hand the repetitive work to software so your people spend more time on the work your customers actually pay for.

Bring the first course to your team

Tell us about your business and we’ll suggest where to start — usually a single half day.

contact@tailoored.com

Sources — every number on this page

  • Goldman Sachs 10,000 Small Businesses Voices survey, 2026
  • Salesforce, Small & Medium Business Trends Report (6th edition), 2025
  • U.S. Chamber of Commerce Foundation, Main Street AI Monitor, 2026
  • BCG, AI at Work 2025: Momentum Builds, but Gaps Remain, 2025
  • TeamViewer SMB AI survey, 2025
  • Reimagine Main Street / PayPal, Beyond Efficiency survey, 2025
  • Thryv, 2026 AI and Small Business Adoption Survey
  • Ruzuku, Cohort vs Self-Paced Courses data report, 2026
  • U.S. Chamber of Commerce / Teneo, Empowering Small Business report, 2025
  • Pertama Partners, Corporate AI Training Cost benchmark, 2026
  • MIT Sloan Executive Education, AI: Implications for Business Strategy, 2026

Taught by the team behind this agent workshop kit — we build with this stuff every day.