AI Training That
Actually Sticks
I run hands-on AI workshops for teams at organisations like Thomson Reuters, Downer, Just Eat Takeaway, and the Australian Institute of Management. No slides-and-theory — your people leave using AI the same day.
Trained teams at Thomson Reuters · Downer · Just Eat Takeaway · AIM · West London Business
I wasn't early to AI because of ChatGPT — I was selling AI-made work eight months before it launched.
In February 2022, nine months before ChatGPT existed, I was running AI image pipelines on rented cloud GPUs and building a business around the results. By June 2022 OpenAI had invited me into their DALL·E 2 early artist access programme. When ChatGPT arrived that November, I'd already done the confused-beginner phase — so I could start teaching almost immediately.
That head start matters for one practical reason: I've watched this cycle before, and I know the difference between what's hype and what your team can actually use on Monday morning.
Founded an AI art business running CLIP-guided generation pipelines — nine months before ChatGPT.
Invited into OpenAI's DALL·E 2 early artist access programme.
Sold AI artwork through Art Lovers Australia — from a practice built long before ChatGPT.
First corporate AI briefing (West London Business) ten weeks after ChatGPT launched. Teaching continuously since.
On stage at Getty Images' Prompt Battle, SXSW Sydney.
Corporate AI training for Downer, Just Eat Takeaway, Thomson Reuters and the Australian Institute of Management.
See It, Don't Take My Word For It
Two minutes on what the work looks like — twenty years of production, and where AI fits now.
Plays via YouTube's privacy-enhanced player — nothing loads until you press play.
Why Your Team Needs This Now
Your team is already using AI
68% of Australian workers are using AI tools at work, many without training or policy. The question is not whether to adopt — it is whether to adopt safely.
Generic training doesn't work
One-size-fits-all webinars don't change behaviour. Your team needs practice with their actual tools on their actual problems.
The risk of waiting
Every month without training is a month of unguided AI use, data leaks to consumer tools, and productivity left on the table.
Three Steps to Impact
Discovery Call
We talk for 20 minutes. I learn what tools your team uses, what problems they face, and what outcome you need.
Tailored Workshop
I build a session around your team's actual workflows — not generic demos. Three hours or a full day, in-person or virtual.
Ongoing Access
Every participant gets access to the full interactive course portal with 40+ lessons, tools, and resources they can revisit.
Workshops Available
Each workshop is tailored to your team. These are the core programmes I deliver most often.
Mastering AI Tools
46 interactive lessons covering AI fundamentals, prompt engineering, strategic thinking with AI, and productivity workflows. Perfect for any professional team.
Book This WorkshopAI for Defence & Government
Built for DISP members, Defence APS staff, and government contractors. Covers the Australian policy stack, ISM-2074, approved providers, shadow AI risks, and data sovereignty. Fully offline delivery available.
See the Government PageAI for HR Teams
Recruitment automation, performance analytics, L&D transformation, employee experience, and workforce planning with AI.
Book This WorkshopCustom / Industry-Specific
Tailored to your sector. Previous custom builds include creative teams, educators, corporate leadership, and technical teams.
Discuss Your NeedsWhat Makes This Different
Author, not aggregator
I wrote The AI-Native Playbook. This is not repackaged content — it is built from first principles by someone who builds with AI daily.
Filmmaker's eye for engagement
20 years in creative production means every workshop is designed to hold attention, not just deliver information.
AIM partnership
I deliver through the Australian Institute of Management — one of Australia's most respected training institutions.
Interactive, not passive
Every lesson has hands-on tools, quizzes, decision trees, and exercises. Participants do, not just watch.
Clear, Simple Pricing
All prices in AUD, ex GST. Every engagement is tailored on a discovery call first — these are honest starting points, not surprises.
3-Hour Workshop
- Up to 15 participants
- Hands-on training built around your team’s actual tools and workflows
- Full course portal access for every participant
- Virtual or in-person
Full-Day Workshop
- Up to 15 participants
- 8 hours of deep-dive, hands-on training
- Full course portal access for every participant
- Virtual or in-person
Executive 1:1 Session
- 90 minutes, one-on-one
- Strategic AI roadmap and risk briefing — no jargon
- 5-session package available
- Virtual or in-person
Keynote
- 30–60 minute keynote for conferences and company events
- Tailored to your audience and industry
- The pre-ChatGPT story, told with receipts — see the Speaking page
- Plus travel
Guest Lecture
- Universities and industry associations
- 1–2 hours, lecture plus Q&A
- Practical, current, and honest about what AI can’t do
- Virtual or in-person
Additional participants around $1,000 per extra 10 people. Travel billed at cost outside Sydney. Virtual and in-person options for everything. Volume and multi-session discounts available — and community and non-profit rates by discretion. Just ask.
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.”
“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.”
“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.”
“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.”
Trusted Across 20 Years of Production and Training
Two careers, one skill set. I say exactly which is which — because you'll ask in procurement anyway.
Thomson Reuters · Downer · Just Eat Takeaway · Australian Institute of Management · West London Business
SAP · Getty Images · KPMG · Deloitte · Fujitsu · Swarovski · Nike · Nissan · Toyota
750+ videos delivered, filmed in 30+ countries — including an 11-year relationship with SAP.
The Things People Actually Ask
How many people can attend?+
Workshops are priced for up to 15 people, which is the size where everyone still gets hands-on attention. Beyond that, additional participants are around $1,000 per extra 10 people — larger groups work well for keynote-style sessions, less well for hands-on training.
Virtual or in-person?+
Both, and both work. I'm based in the Blue Mountains and deliver in-person across Sydney at no extra cost; elsewhere, travel is billed at cost. Virtual sessions are run properly — interactive, hands-on, cameras optional — not a webinar you can leave running in another tab.
How customised is the session, really?+
Genuinely customised. The discovery call tells me which tools your team already uses, what they're allowed to use, and what problems eat their week. The exercises are then built on workflows they'll recognise. Nobody learns AI from someone else's use cases.
What about the privacy of our data and examples?+
Nothing confidential goes into an AI tool during training. Exercises use sanitised or synthetic versions of your workflows, and part of every session covers exactly this: what your team should and shouldn't paste into which tools. Happy to sign an NDA before the discovery call if that's easier.
How does invoicing work? Can you handle our PO process?+
Yes — I work with procurement and purchase-order processes regularly. Standard terms are 50% on booking, balance net 14 after delivery. Invoices come from Film Me Pty Ltd (ABN 57 512 132 395), which holds business insurance through NRMA.
Film Me Pty Ltd
ABN 57 512 132 395
NRMA Business Insurance
POs, vendor onboarding and NDAs — all fine
50% on booking,
balance net 14
One page. Made to be forwarded to whoever signs things off.
Let's Talk
The best way to find out if this is right for your team is a 20-minute call. No pitch deck, no pressure — just a conversation about what you need.
Book a Discovery CallOr email ru@rupertchesman.com