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Hi folks

This month we're chatting with Leigh Gibson, who's helping SMEs navigate AI safely and has real insights on scaling tech teams. As we head into Q4, we've also rounded up the latest meetups, open roles, and some seriously good reads to help you stay sharp.

Stay curious, keep building 🛠️
Lookahead crew 🐥

 
 

Friends

Let us introduce you to Leigh Gibson:

Leigh Gibson

Introduce yourself

Hi Everyone, my name is Leigh (pronounced Lee), I don't have any nicknames, and I love to read. This got me into trouble as a kid because I would lose myself in fictional worlds and sometimes get in trouble for reading books under my desk at school when I was bored! 😅

What do you do for work?

I'm establishing a new tech consultancy, Tech Exec Australia, to help SME businesses without a full-time CIO/CTO make strategic technology decisions and set them up to use AI safely (practical and adaptable AI governance).

I started out as an engineer. My experience—both as a bootstrapped founder for 3+ years and leading large tech platforms in regulated industries (internet banking for a big 4 bank + global employee tech for Australia's largest telco)—means I know how to own and manage technology in a way that is appropriate to customer needs.

What do you do outside work?

My family enjoy sailing Couta boats through summer in Victoria's Port Phillip Bay. They are vintage-era wooden fishing boats designed for speed at a time when the first boat back to shore would get the best price for their catch. No automated components allowed and the fastest boats are often the ones with a calm skipper, team of people with clearly explained/understood roles, high trust and great communication. Just like tech delivery! 😉

I also enjoy sewing and inventing new houses/toys for my family's pet guinea pigs from recycled materials. It's a win-win because my kids enjoy the creative building process and the guinea pigs find the new inventions entertaining and mentally stimulating.

You led the largest Microsoft Copilot rollout in Asia Pacific for Telstra. What's the biggest misconception you see business owners have about rolling out AI tools like Copilot internally?

The biggest misconception that I see is the assumption that employees understand how to maximise benefit from using the tools without needing any training. Or that AI can support work being transferred to new team members without prior planning. The majority of teams who use tools like Copilot well and enjoy significant benefit have spent time establishing appropriate structural foundations to ensure success. Most beneficial supports to teams have included train the trainer type activities to localise support, weekly prompt ideas shared on the company intranet, and intentionally communicating the 'boring stuff' (information security, data protection, data quality and provenance, and specific legal implications). 

Currently, the people I see who gain the most benefit from creating new AI agents are people who deeply understand the underlying business drivers for their work and can anticipate how to navigate any undocumented rules or processes. Anyone can create a new agent, but those who recognise specific pain points and know how to address them with an agent generate the most benefit.

You've done AI governance for both scale-up and enterprises. What does each end of that spectrum get right that the other could learn from?

When starting to use any new type of technology, it's useful to run structured experiments with new AI tools initially to quickly validate value and effectiveness. Scale-ups are great at experimenting but could benefit from appropriately structured quality checks and establishing controls before launching. The transition from startup to scaleup can be tricky if the team culture does not evolve to accept a baseline level of important checks prior to launching something new. This is critical when a scale-up operates in a regulated industry - shortcuts acceptable in the early years are likely to be frowned upon by their regulator now, especially as potential cyber risks grow quickly.

Enterprises are also experimenting with AI tools and most have extremely rigorous processes to follow due to the catastrophic potential risk triggered by the wrong decision, so the evaluation and deployment speed can feel painfully slow. Senior stakeholders sometimes need bravery and deep breaths to provide final approval when the timeframe is shorter than usual - even after all of the processes have been followed!

You're co-founder of Technology Executive Women (TEW) - what prompted starting it in 2022, and what's changed for women in tech leadership since?

In 2020, I had completed the modernisation of ANZ's internet banking platform and was asked to move to a new part of the bank (outside Digital) to establish a new tech team. There were 6 women leaders in Digital whom I had sponsored into their roles, and they wanted to stay in touch. I established a fortnightly meeting since my new role was quite busy, and invited some other female tech leaders I met at ANZ who expressed interest. Within 6 months, more than 50 women working in tech leadership roles across the bank were actively participating! We realised that the group was useful for connecting people with similar skills and experience so they could support each other.

I accepted a redundancy from ANZ in 2022 and decided to co-found Technology Executive Women with Sam Davies that year so we could keep the group going outside ANZ. Forming an independent body allowed us the freedom to focus specifically on supporting, connecting and empowering our members. We don't meet often, but the energy in the room is magical when we do! :) While progress is being made on technology leadership diversity, there are peaks and troughs to navigate as the work continues.

Any podcast you are currently listening to, or a book you are reading?

Here are two books I've enjoyed in the past year, both written by members of Tech Exec Women :)

"The Quality Coach's Handbook" by Anne-Marie Charrett - super useful guide for technology leaders wanting to ensure their engineering teams maintain a focus on quality and a fantastic resource for anyone seeking to continuously improve how they build software.

'Win the Night to Win the Day' by Penelope Barr - a thoughtful personal productivity strategy book based on her experience as a senior technology leader.

What is your favourite tool or resource, and why?

Claude is my favourite at the moment because it helps in various contexts. Tools and resources are constantly evolving, so I don't typically get too attached.

Your one-sentence work-related advice

The best way to tackle a really HUGE change is by ensuring every small daily decision supports it. This effect expands exponentially when teams focus this way because many more minds are involved in achieving the shared goal.

 
 
 

Coming up

Sydney Tech Leaders: Crucial Conversations
Thursday, Sep 3, Sydney

In-person discussion on having difficult yet important conversations, featuring speakers Molly Rowe, Gabriel Wainmann, and Sam Elderfield, with networking and food provided.

Python WA Meetup
Thursday, Sep 3, Perth

Learn about MicroPython and migrating documentation from Sphinx to Markdown, hosted by Bankwest.

Hack For Humanity
Saturday, Sep 5, Sydney

A no-code hackathon where student teams from multiple unis partner with real non-profits to solve genuine challenges, with ongoing support and $2,000 prize pool for winning projects.

Cicada x Tech23 
Wednesday, Sep, Sydney

Australia's biggest deep tech festival showcasing 23 promising startups across AI, quantum, biotech, sustainability, and advanced manufacturing, with 400+ investors and industry leaders. 

Claude for Developers Meetup
Thursday, Sep 10, AWS Sydney

Enjoy lightning talks, have a slice of pizza, a beverage, and mix and mingle. Meet your local community.

Elixir Sydney: Hack Night
Wednesday, Sep 16, Sydney

A small, in-person-only interactive Hack Night. Bring your ideas, projects and your laptop and be ready to code.

Founders Unfiltered
Thursday, Sep 17

Fireside chat with Francois Henrion, co-founder of Paytron (a fintech that raised $4.35M to help SMBs manage finances), sharing unfiltered growth stories and lessons learned.

NSW AI Bonanza 2026
Sep 23 - 25, Sydney

A multi-day festival celebrating technical and creative AI innovation, featuring the NSW AI Awards, with events at iconic venues including Bondi Icebergs.

MongoDB User Group
Thursday, Sep 24, Sydney

Developer meetup featuring talks on MongoDB Atlas Search internals and cost-efficient LLM applications with MongoDB, plus networking and pizza.

 
 

Featured Jobs

Founding Engineer
Founding Engineer at an early-stage, well-funded AI startup. Sydney hybrid. Competitive base + founding-team equity.

Product Designer
Product Designer (3–5 yrs) to join a small, remote-first design team at a fast-growing consumer app. Mobile app design experience essential.

Forward Deployed AI Engineer
Build AI-native businesses. As a Forward Deployed Engineer, you'll apply frontier AI, ML, & LLM tech to real-world operations, delivering impact fast.

For more opportunities head to our website or sign up for our job alerts.

 
 

Worth Sharing

Beyond Benchmarks
From the team at Cadence, a live dashboard tracking how AI coding models perform in real sessions, not lab benchmarks. Worth a scroll if you want a sense of which models are actually holding up day-to-day, including which ones frustrate developers the most.

Judgment Has to Travel Without Us
A good read on what happens to design quality when product managers and engineers start building without a designer in the room. Makes the case that design judgment needs to be built into the system and process, not just held by one person.

A Fresh Definition of the Product Role
Marty Cagan on what actually separates a strong product manager in the AI era. Useful if you’re hiring product people right now and trying to pin down what matters versus what’s just noise.

How I Built This — Exploding Kittens
The story of how a Sharpie-modified deck of cards turned into a $9 million Kickstarter and 60 million games sold — a good listen if you want a break from the usual tech headlines.

 
 
 
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