A woman and man standing outside, smiling at the camera near a gray tiled wall, wearing business casual attire.

A young woman with long dark hair, wearing a dark blazer and a necklace with a cross pendant, smiling at the camera against a plain light gray background.

Behind the screens

The Software Coach is run by us, Josh and Courtney Wilson.

We started our careers in very different corners - Josh as a Chartered Accountant, and Courtney as a freelance Graphic Designer, working in fast-paced print and branding projects. But over time, our paths converged around a shared belief: business software should make life easier, not harder.

Josh was shoulder-tapped to lead Sidekick Cloud, the software and systems arm of Sidekick Chartered Accountants. As demand for hands-on help with implementation and integration grew, that division evolved into its own business -The Software Coach.

Since then, we’ve doubled down on what we do best: helping business owners streamline their systems, improve team processes, and get the best out of tools like Xero, WorkGuru, and Projectworks.

Who you’ll be working with

Josh dives into the strategy, numbers, and systems that make sense for your business.
Courtney leads the project from start to finish, making sure your team is clear, supported, and moving forward.

Camille analyses data, designs templates, identifies problems

Together, we’re here to help you find more insight, more structure - and more freedom in your business.

Team Bios

Director | Software Consultant
Josh is a member of the Xero Partner Advisory Council (XPAC), holds a BA and a BCom from the University of Otago and is a full member of Chartered Accountants Australia and New Zealand (CAANZ). He has specialised in accounting software since 2014 and is a registered partner with products such as Unleashed, WorkGuru and Xero.
Josh’s longterm expertise as both a software specialist and Chartered Accountant as well as his genuine commitment to his clients, makes him one of the best people to entrust with the long term health of your business.
Managing Director | Communications
Courtney holds a BA in Design Studies from the University of Otago, with a particular focus on print, brand identity and marketing.
She now manages the business and communications for The Software Coach, overseeing our wider team and managing our onboarding and discovery sessions.
She will be your main point of contact over the course of your project and is constantly researching and implementing new tools, products and processes to help us help our clients.
Camille is our fabulous off-shore worker who supports us behind the scenes with software and data management. She has been rapidly upskilling in job and stock systems and is working on a new project to develop custom designed document templates.