MyTrucking introduces the sector to Ollie, its own AI helper, and how the technology is helping operators receive immediate support.
It’s 4:30 pm and the dispatcher’s phone is ringing with last minute updates and driver queries. They spot a cancelled job on tomorrow’s day sheet but can’t recall how to remove it. They don’t have time to call for support, so they jump into the systems chat box to ask for help.
Across Australia, AI chatbots are stepping in to provide vital answers and instant support about job management software. Ready to see what’s possible? Let’s dive into MyTrucking’s top tips from more than eight years of working with our AI helper – Ollie.
Shaping Australian trucking, one chatbot at a time
Firstly, what is an AI chatbot? An AI chatbot is a computer program that can chat with people in a way that feels natural (using text or voice) by understanding what is said and then replies.
With technology and automation developing at a rapid pace, we’re seeing more AI chatbots stepping in to enhance the customer experience (when done well).
Common AI chatbot types used in the transport industry:
- Generative AI Chatbots
Enables customers to ask complex, open-ended questions in plain language.
- Keyword Recognition Chatbots
These can be set up for fast, automated replies to common queries.
- Voice Chatbots
These can be set up to allow drivers to interact safely while on the road.
- Conversational AI Chatbots
These can be set up to diagnose issues and offer solutions.
Case study: Smart tech, human heart – the MyTrucking story
MyTrucking is simple, powerful job management software for transport operators. We’ve chosen to use a conversational AI chatbot, Ollie, to engage with our customers via the chat box within MyTrucking.
Ollie is smart, personable, and named after our founder’s much-loved Jack Russell. Ollie is a conversational, retrieval‑augmented AI chatbot that guides users to solutions step‑by‑step.
He draws only on up‑to‑date, company‑specific information from our Help Articles, so always sounds distinctly ‘MyTrucking’.
The benefits of Ollie are that he replies immediately, offers simple, straightforward guidance and provides links to more detail if needed.
We value transparency, so we always state when it’s Ollie behind the chatbox. If a customer prefers to talk to a real person, they can simply click the ‘Talk to a person’ button (and during office hours, one of our support team will jump straight in).
In July 2025, Ollie was involved in 36.6 per cent of new conversations from MyTrucking customers.
Advice for ‘employing’ an AI chatbot
Ollie’s skills haven’t just happened overnight. Our team of real people have been training him for years!
Like a proud dog-Mum, Nicole Yee (MyTrucking’s customer support specialist) is a proud AI chatbot trainer. Nicole has been with MyTrucking since 2021 and shares the positive impact Ollie has had.
“Integrating an AI chatbot into our support workflow has been a game-changer. It saves us a tremendous amount of time, delivers faster responses to customers, and scales effortlessly with our growing customer base, without the need to constantly expand our team. Plus, managing it is genuinely fun and rewarding,” Yee says.
Any advice for companies thinking of ‘employing’ a conversational AI chatbot?
“Give it a go! It is great and can provide 24/7 support. Just ensure help content is up to date and monitor the responses to make sure any incorrect responses are looked into to see if help content needs to be adjusted. It’s so easy to use once you get the hang of it,” Yee says.
Step into the future of transport management. Trial MyTrucking for free.
*This article was originally published in Owner Driver – August 2025.
