Now Booking Q3 & Q4 2026

Bring AI Training
To Your Team

Full-day workshops, executive briefings, keynote speaking and ongoing AI consulting — tailored to your organisation's goals, industry and team.

700+
Students This Year
70+
Countries
200+
Workshops Delivered

Trusted by Teams At

Thomson Reuters Swarovski SAP Toyota Nissan Nike Australian Institute of Management
What We Offer

Training & Consulting Services

Four core offerings designed to meet your team wherever they are on their AI journey — from first steps to full-scale adoption.

$5,000
Starting From

Team Workshop

Full-day, hands-on AI training for your team. Participants leave with practical skills they can apply immediately — not slides they'll forget.

  • Up to 20 participants per session
  • Customised curriculum for your industry
  • Live demos with your actual tools and workflows
  • Post-workshop resource pack and recordings
  • 30-day follow-up support via email
Book Workshop
$2,000
Starting From

Executive Session

A focused 3-hour deep dive designed for leadership teams. Understand the strategic AI landscape, identify high-impact opportunities, and build a roadmap.

  • 3-hour intensive strategy session
  • AI readiness assessment for your organisation
  • Competitive landscape and opportunity mapping
  • Custom AI adoption roadmap document
  • C-suite friendly — no jargon, just clarity
Book Session
Custom
Quote on Request

Keynote Speaking

Energise your conference, summit or company event with a keynote that cuts through the AI hype and delivers actionable insight your audience will remember.

  • 30 to 90-minute keynote presentations
  • Live AI demos that wow audiences
  • Topics tailored to your event theme
  • Available in-person or virtual (worldwide)
  • Attendee takeaway resources included
Enquire Now
Ongoing
Retainer Available

AI Consulting

Long-term AI strategy and implementation support. From identifying automation opportunities to building internal AI champions — I embed with your team.

  • Monthly strategy and review sessions
  • Workflow audit and automation design
  • Train-the-trainer programme for internal champions
  • Tool selection and vendor evaluation
  • Priority Slack/email access between sessions
Discuss Retainer
Popular Workshops

Workshop Topics

Every workshop is customised to your team, but here are the most requested topics. Mix and match, or request something bespoke.

Prompt Engineering Masterclass

From zero to advanced prompting across ChatGPT, Claude, Gemini and more. Structured frameworks your team can use daily.

AI Workflow Automation

Build automated workflows using AI tools, APIs and no-code platforms. Identify and eliminate repetitive tasks across departments.

AI for Creative Teams

Image generation, video AI, copywriting assistance and design workflows. Built for marketing, design and content teams.

AI Governance & Ethics

Build responsible AI policies, understand data privacy risks, and create guardrails that protect your brand and customers.

Building AI Agents

Design, build and deploy custom AI agents for customer service, data analysis, research and internal operations.

AI for Data & Analytics

Natural language querying, automated reporting, predictive insights and AI-enhanced dashboards for data-driven teams.

Don't see your topic? Get in touch — every workshop is built around your needs.

How It Works

From Enquiry to Impact

A clear, straightforward process — designed to deliver maximum value with minimum disruption to your team.

1

Discovery Call

We discuss your goals, team structure, industry context and current AI maturity. 30 minutes, no obligation.

2

Custom Proposal

I design a tailored curriculum with specific exercises, demos and case studies relevant to your organisation.

3

Deliver & Train

Interactive, hands-on delivery — in-person or virtual. Your team works with real tools on real problems, not hypotheticals.

4

Follow Up

30 days of email support, recordings, resource packs and an optional follow-up session to check progress and troubleshoot.

Client Feedback

What Clients Say

“Rupert's up-to-the-minute knowledge of this space is incredibly impressive… This is not someone who learned a set of content once and delivers it on repeat. He is a skilled and experienced facilitator who makes the subject matter fun, interesting, and accessible without ever dumbing it down.

I'd recommend Rupert without hesitation to any individual or organisation looking to genuinely understand and make the most of AI tools.”

Jenny Steadman
TEDx Speaker · National Director, Potential Project
LinkedIn recommendation · Mastering AI Tools, June 2026

“What stood out most was Rupert's ability to simplify AI concepts and turn them into practical, actionable insights. The session was well-structured and interactive.

I would strongly recommend Rupert to professionals and learners who want to understand and apply AI tools like ChatGPT in a meaningful way.”

Taruna Kalra
Senior Business Analyst · Toyota Finance Australia
LinkedIn recommendation · AI for Productivity (Australian Institute of Management), January 2026

“Rupert's sessions are highly interactive, hands-on and filled with real world, real time demonstrations. His enthusiasm is infectious, and his warm, inclusive facilitation style creates an environment where everyone feels comfortable participating and learning.

His commitment to continually explore, test and stay at the forefront of the rapidly changing AI space means every course includes the latest developments and practical insights. If you have the opportunity to attend one of Rupert's courses, I highly recommend it.”

Rachell Berrell
FMS Business Partner · System Adoption & Optimisation
LinkedIn recommendation · AI & Automation in Practice, June 2026

“Rupert makes AI feel practical, useful, and far less mysterious than it first seems. No panic. No doom spiral. Just clear explanations, good examples, and the kind of teaching that makes you want to go and try things straight away.

If you want someone who can help people move from curious-but-confused to actually using AI well, Rupert is absolutely your person.”

Jen Berkley
Application Support Analyst · AI Enablement & Education Systems SME
LinkedIn recommendation · Mastering AI Tools, June 2026
Rupert Chesman
Your Trainer

Meet Rupert

I've taught over 700 students in the past year alone, in practical AI skills. My background spans digital marketing, creative production and technology education — which means I understand how AI fits into real workflows, not just theory.

I've delivered workshops for teams ranging from 5-person startups to large enterprises. Whether your team has never touched ChatGPT or you're building custom AI agents, I meet people where they are and take them further than they expected.

My philosophy is simple: AI training should be practical, human-centred and immediately useful. No jargon. No hype. Just skills your team will actually use on Monday morning.

700+
Students This Year
70+
Countries
Full Bio & Background

Frequently Asked Questions

Ready to Upskill Your Team?

Book a free 30-minute discovery call to discuss your team's needs, or send me a message with your requirements and I'll get back to you within 24 hours.

Response Time
Within 24 hours
Location
Worldwide (in-person & virtual)