Jagged Peaks Travel Club

AI workshops for teams
at any stage

From curiosity to capability
explore what's possible with AI

Joshua Crowley
Joshua Crowley LinkedIn
Workshop locations map

Hey, I'm Josh, an AI educator passionate about making AI accessible to everyone. The landscape is moving incredibly fast, and I believe people deserve honest, practical information about these tools, not just the hype.

Through hands-on workshops, I create space for your team to experiment, play, and build genuine confidence with tools like ChatGPT, Claude, Cursor, and Lovable. I love the challenge of unpacking AI's "jagged intelligence": showing people where it's brilliant, where it stumbles, and how to navigate both. This framing helps teams see the real opportunities and challenges, which makes the investment in learning these skills feel worthwhile.

Maybe you've heard about these tools but aren't sure where they fit, or you're already using them and want to level up how your team works with them. Perhaps you're a leader trying to bring everyone along, or you've got a mix of beginners and power users who need a shared foundation. Wherever your team's at, I adapt the workshop to meet you there.

My workshops bring people together to explore what actually works for your context. We identify risks early, build shared understanding, and discover how these tools can align with your team's values. The goal isn't just competency. It's making AI feel effective, enjoyable, and genuinely useful for everyone.

Book a Discovery Call

No pressure, let's chat about whether a workshop is right for your team

Mountain crackMountain grotto

Testimonials

Jesse Yuen

"Josh brought a refreshing level of honesty, humility, deep curiosity, immediately made us all feel safe and led a workshop which we all loved. I can't recommend Josh enough if you suspect your team might need a gentle nudge into a space that seems kind of scary from the outside looking in."

Jesse Yuen
Head of Product Design – Hireup

Alessio Somma

"Joshua facilitated a great workshop as part of Design Outlook on using Cursor to develop Multimodal apps. His practical tips gave me more confidence both in getting started and in what I was doing!"

Alessio Somma
Senior Experience Designer

Elizabeth

"Josh successfully tailored his AI training to our building-industry team. He kept it practical and relevant (without being overly technical), and the hands-on format had everyone engaged. The impact was immediate: the team started using what they'd learnt right after the session. We're now setting up 1:1 coaching sessions with Josh and planning regular team check-ins to keep the momentum going. Highly recommend for any team looking for practical use cases, engaging content, and training that genuinely delivers value."

Elizabeth
Director – Greensmith & Co.

Watch my approach

Companies I've Worked With

Easy Agile

Professionals at Easy Agile

HireUp

Designers at HireUp

Greensmith & Co

Architectural Builders at GS and Co

Workshops

I can help your team find and adopt the AI tools that genuinely fit your workflow and needs.

ChatGPT

ChatGPT Workshop

I ran a ChatGPT workshop for the team at Easy Agile to give everyone a detailed understanding of ChatGPT's features, including the subtle, hard-to-discover ones. We established a shared framework and language for successful AI interaction, equipping the team with practical day-to-day strategies. 88% of participants felt more confident using ChatGPT after the session.

Cursor

Cursor Workshop

Engaged by Hire Up to onboard their design team to Cursor, a real challenge as the tool can initially feel quite hostile to non-developers. By carefully explaining the interface and scaffolding our tasks, we had designers building sophisticated AI prototypes with frontier models from Google. This gave the team confidence to experiment at the cutting edge and helped leadership understand how to best utilise these advanced capabilities.

Lovable

Lovable Workshop

In my community Lovable workshop, I showed designers and product managers how to go from zero to one with prototypes. We unpacked my approach to prompting using voice input, how to leverage API documentation for better code generation, and specific techniques for iterating through Lovable's built-in editor. Participants walked away understanding how to get genuinely powerful results from the tool.

Claude

Claude Workshop

Construction documentation and paperwork can be overwhelming. I worked with Greensmith and Co to show how Claude Projects could help them analyse and produce documents for site visits, work estimates, and trade schedules. By explaining AI best practices and how Projects work, the team discovered time-saving efficiencies that would let them spend less time at their computers. By lunch's end, they were buzzing with ideas for a more effective workplace.

What Makes Jagged Peaks Different

🎯 Tool-Agnostic Approach

I'm not a vendor or paid by any companies to promote their app. When I introduce a tool to your team, it's because I genuinely think it's a good fit and meets your requirements.

🤝 Hands-On Learning

In class, people get to see their approach working or not working in real-time, and we adjust together. This collaborative problem-solving builds confidence, not confusion.

✨ Customized for Your Team

I adjust the workshop content and delivery to meet your team's specific requirements. This ensures the material is accessible and everyone can see a real pathway to mastery.

🎓 Experienced Educator

I've taught at UTS and General Assembly. I'm an educator first with a passion for teaching, and AI is probably the most interesting subject I've had the opportunity to teach.

🏔️

Why "Jagged Peaks"?

We're in a unique phase of AI called "jagged intelligence," where systems can achieve olympiad-level mathematics but fail to count letters in "strawberry." AI's capabilities rise and fall unpredictably, like a mountain range. Understanding this jagged frontier is essential for deploying AI safely and effectively.

Read the full story

Who I Work With

🔍 Curious Explorers

You've heard about ChatGPT and AI coding tools, but don't know where to start or if they're relevant to your work. Perfect, that's exactly where most people begin.

🚀 Forward-Thinking Leaders

You see the potential but need help introducing AI to your team in a way that's empowering, not overwhelming. You want everyone on board, not just the tech-savvy few.

📊 Partial Adopters

Some team members are using AI tools informally, but there's no shared understanding or best practices. You want to level everyone up and establish good habits.

⚡ Ready to Scale

Your team is already using AI, but you want to ensure everyone's using it effectively, safely, and in line with company values.

Frameworks

Three Cs Framework: Context, Capabilities, and Consent

My workshops introduce participants to different frameworks for thinking about working with AI. The first one is the three Cs: context, capabilities, and consent.

Having a shared language to describe good AI is one of the first steps for unpacking how the better user utilizes these tools and be able to verify their outputs.

Community Workshops

Workshop badges

Join one of my free workshop for the community. Here's a list of my upcoming ones. Come along and join. I'd love to show you what I've been playing around with recently.

About Josh

Josh Crowley

Josh is a seasoned designer and educator with over 10 years of experience building digital services and products for organisations like the ABC, CHOICE, Time Out and the University of Canberra – and teaching experience with General Assembly and UTS.

Josh started Jagged Peaks Travel Club to serve as a guide in this emerging AI landscape, running community workshops helping people unpack new tools and best practices for AI apps: Cursor, Lovable, ChatGPT, and Claude. Josh uses his skills as an educator to help individuals learn from each other, and to demonstrate best practice thinking and techniques.

Josh is also a Cursor Ambassador learning from expert users globally, whilst organising the Sydney Cursor meetup locally. Josh has his own AI app for Dads called tinytalkingtodos.com .

Learn more at joshuacrowley.com .

Frequently Asked Questions

What kind of services do you offer?

We'll start with a quick call to understand where you're at and what tools you're currently using or have in mind. From there, I'll send you a proposal with a clear outline of what I'll deliver and my costs.

For most teams, this means a workshop focused on onboarding your team to a particular tool and ensuring everyone can use it effectively. After the workshop, I can offer one-to-one support sessions to help team members apply what they've learnt to their day-to-day work.

What's included: Full workshop recording, all materials and resources shared via a FigJam board, custom prototypes built during the session, and the opportunity to review workshop content with me prior to delivery.

Some teams also request a report at the end that sums up the engagement, analyses your team's current AI capabilities, and provides actionable goals for moving forward.

What tools do you teach?

I work with a broad range of AI tools: developer-focused ones like Cursor, general-purpose tools like ChatGPT, Claude, Gemini, and Microsoft Copilot, as well as AI-enhanced apps like Airtable, Granola, and Notion. While the specific tools vary depending on your workplace policies, my workshop approach and strategies remain consistent, built on what I've learnt actually works.

Will you sign an NDA?

Yes, of course. I'm happy to sign an NDA and keep any confidential information about your business private.

What are your rates?

I offer transparent pricing to help you plan your budget. All prices are in AUD and include GST. Sydney metro area travel is included; other locations may incur additional travel costs.

💡 Single Workshop (Most Popular)

$2,500 - $4,500 AUD

3-hour hands-on workshop for up to 20 people. Includes all materials, full recording, FigJam resources, and follow-up support. Best for teams wanting to onboard to a specific tool.

🎯 Workshop + Coaching Package

$5,000 - $7,500 AUD

Initial 3-hour workshop plus 5 x 1-hour individual coaching sessions. Includes custom support materials tailored to your team's needs. Best for teams wanting sustained support and skill development.

🚀 Multi-Workshop Program

$12,000 - $20,000 AUD

Series of workshops over 4-8 weeks covering multiple tools (ChatGPT, Cursor, Claude, etc.). Includes ongoing Slack/email support and final capability assessment report. Best for organizations building comprehensive AI capabilities.

Not-for-Profit & Small Business: I offer flexible pricing for NFPs and small businesses. Let's have a conversation about what works for your budget.

How long are your typical workshops?

Most workshops run for three hours, though I can structure multiple sessions over a week depending on what works best for your team's schedule and learning goals.

Do you offer remote workshops or only in-person?

I'm set up for both remote and in-person delivery, though most workshops are conducted remotely. This makes it easy to work with distributed teams or fit sessions around busy schedules.

What size teams do you work with?

I work with groups ranging from small teams through to 40+ participants. I'm able to scaffold the workshop content to meet your team's specific requirements, regardless of size.

What if our team has mixed skill levels (some beginners, some advanced)?

My workshops are designed assuming no prior knowledge, so beginners get a well-scaffolded experience that builds in complexity. Advanced users benefit from my framework for thinking about AI and foundational techniques they may not have encountered despite knowing the features. Everyone walks away with something valuable.

What industries or types of teams do you typically work with?

I work across any industry. These tools are accessible to any team that uses computers. So far, I've run workshops for office professionals, remote designers, construction teams, and more. The principles translate regardless of your field.

How hands-on are your workshops?

Very hands-on. This is my secret sauce. We actively use AI tools during the session, compare results, and share what we're discovering in real-time. This generates organic conversations about what's working, what's not, and we exchange tips and tricks as we go. Participants should bring laptops and have access to paid accounts for whichever AI tool we're focusing on.

Can we record the workshops?

Yes, I always provide a Zoom recording afterwards, along with access to a FigJam board that contains all the material from the workshop. This means you can revisit concepts and share resources with team members who couldn't attend.

How do I measure success after the workshop?

Through the one-to-one support sessions I offer after the workshop, I work directly with your team members to document how they're adapting based on the content provided in class. This creates clear, measurable insights into skill development and practical application. You'll see exactly how your team is progressing and where additional support might be valuable.

What's your cancellation or rescheduling policy?

I understand that schedules can change. Please contact me as early as possible if you need to reschedule, and I'll work with you to find a new time that suits your team.

Ready to Get Started?

Book a quick discovery call to discuss your team's needs, or connect via LinkedIn.