Dean Chadwick knows the value of starting from scratch – especially when the stakes are high.

As a driving force behind Solo by MYOB, Chadwick helped conceive and launch a mobile-first solution targeting sole traders, Australia and New Zealand’s largest and most underserved small business segment.

First as CMO and now as COO, Chadwick stepped into the Chief Commercial Officer (CCO) role in November 2024 after 18 months leading marketing, now taking on a full P&L role responsible for 68 per cent of company revenues and its largest customer segments.

Effective marketing strategy

Chadwick posed a bold question early on: How often can a B2B organisation act and behave like a B2C brand, delivering product innovation through a new brand proposition in Australia? His answer: “Welcome to Solo MYOB.”

With 1.9 million sole operators representing 61 per cent of the total addressable market, Chadwick’s strategy combined product innovation, brand creation, and sharp execution with a clear audience focus: tradies, health and wellness, professional services, arts, education and admin.

“These people are the lifeblood of our communities and economy,” Chadwick says. “This is a brand-new product for an underserved audience that is mobile and smart from day one. From a brand  strategy we had a blank canvas allowing us to be highly considered on who and how we want to show up. The  backing of MYOB gave us leverage on existing channels and then freedom to innovate further with the new brand to connect to a younger audience.

“Sole operators face numerous administrative challenges such as invoicing, expense tracking, banking connection, instant payments, and maintaining ATO-ready records. Our new product, Solo by MYOB aims to  simplify these tasks, allowing users to focus more on their primary work rather than administrative burdens.

The Solo creative campaign centres around the theme of "work work," which emphasises the additional administrative tasks sole traders manage.

Using humour and relatability, the ‘Work Work’ campaign featuring comedian Tom Cashman turned tedious admin into a punchline – and MYOB into a hero. It’s Chadwick’s belief in building scalable direct channels that’s guiding the product’s runaway success.

Additionally, under Chadwick’s leadership, MYOB unified its marketing and digital teams into a single, strategically aligned function with a clear mandate: Drive commercial outcomes and reposition MYOB as a modern SaaS company.

With a seat at the executive table, Chadwick led a comprehensive transformation of the marketing function, making it fully accountable for core growth metrics and direct acquisition. Key initiatives included a complete rebuild of MYOB.com, a streamlined operating model to balance business-as-usual efficiency with bold innovation, and the creation of a unified brand proposition supported by a refreshed identity and design system.

Chadwick also championed a high-experimentation culture, leveraging MYOB’s data assets to personalise customer experiences and lift average revenue per user. He oversaw a full-funnel revamp, tracking every lead from marketing qualified to closed won, and brought Sales Development Reps into the marketing team to sharpen pipeline generation. The introduction of a dedicated product marketing function helped clarify value propositions and test new SaaS pricing strategies. All of this was executed with a retail mindset and a daily operating rhythm focused on growth, marking a bold new chapter for the 33-year-old business.

“Given the success of the new operating model, on November 24, the CMO role was expanded to a Chief Customer Officer bringing together our most important customer constituents across accountants, bookkeepers, small businesses and sole operators. A team now of 650 team members across product,  product marketing, design, acquisition, sales, success, retention, support, brand, and digital.” 

Business influence

Chadwick doesn’t see AI as a trend; he sees it as a foundational shift. At MYOB, he’s leading an internal and external AI transformation under the banner ‘AI Everyday’.

At the heart of it all is a belief: AI won’t replace people, but people who don’t use AI may fall behind. Under Chadwick’s leadership, MYOB is making sure its people – and its customers – are ready for what’s next.

He’s championing a vision that “smarter businesses succeed with MYOB AI”, placing artificial intelligence at the core of how the company drives growth, innovation, and efficiency. Internally, that starts with people. AI Everyday isn’t just a slogan; it’s a rallying cry. MYOB has rolled out compulsory training modules on AI Foundations, Responsible Use of AI, and Effective Prompting to equip employees with the tools to confidently explore this new frontier.

Already, the results are material. Within the Customer Enablement team alone, 23 per cent of users reported saving at least three hours in the first week of using Glean’s AI Assistant, with one employee saving 12 hours by automating meeting summaries and follow-ups.

To deepen adoption, Chadwick helped launch a company-wide initiative at the 2025 Kick-Off, introducing AI-focused events and community groups to create safe, supportive spaces for experimentation. Whether an AI pro or complete beginner, every team member is encouraged to explore how using AI every day can supercharge their work.

Data-driven decision making

Chadwick’s default mode is data-first. In his own words: “Data or creative first? Data.”

His data-first mindset was on full display when Xero – MYOB’s main competitor – announced a controversial pricing change in May. Xero raised the price of its most popular products to $90 per month and removed its Payroll-only product altogether, triggering widespread backlash from small business owners.

Rather than follow suit, Chadwick and his team used market sentiment and customer insights to go in the opposite direction. MYOB dropped the price of its Payroll-only product from $12 to $9 per month – and locked in that price for two years. The move reflected a clear commitment to backing small businesses, especially during times of financial pressure.

The team acted fast, launching a digital campaign that pulled no punches: ‘Why pay $90p/m when you can pay $9? Drop the Xero. $9 vs $90’. It was a rapid-response play that rallied MYOB’s support teams and made switching easy for frustrated Xero customers. The campaign struck a chord, earning praise across social media, widespread community support, and even being hailed as “ad of the year”.

Commercial delivery

Taking MYOB from legacy software to modern SaaS was never going to be easy. But in 2023, Chadwick led a full transformation of the marketing and digital function into a unified, high-performing engine with commercial goals at its core.

“In June 2023, marketing took full ownership of direct acquisition via the website. This was an opportunity rich with a web experience that was clunky and dated, a go-to-market play that had limited operating leverage, and a lack of cohesion and focus across channels,” he says.

Under Chadwick’s leadership, MYOB.com underwent a complete transformation. The team delivered a full CMS migration, redesigned navigation, improved journey management, and embedded experimentation powered by data science – all within six months. The result: A 20 per cent year-over-year increase in channel growth.

To capitalise on this momentum, MYOB launched a dedicated SME Growth Marketing team, operating with a retail mindset and daily acquisition targets. The team rapidly matured performance and influencer marketing capabilities, embracing value-based bidding, customer lifetime value optimisation, branded search, and SEO – all focused on driving more efficient customer acquisition costs that scale.

On the brand front, Chadwick’s team executed a series of integrated brand and retail campaigns to build consideration and drive conversion. The standout: ‘Nothing Beats The OG’ – a bold creative platform that cut through a sea of sameness in the market. It reinforced MYOB’s heritage and value, spotlighting that for just $5 per month, customers get powerful software and the backing of 1700 experts. The campaign was built to scale, split into seven product-focused marketing ads that clearly articulated MYOB’s unique advantages.

Clearly, Chadwick didn’t just market the business – he rewired it.

People leadership

Ask Chadwick how he’d describe his leadership style and you’ll hear three words: “Visionary, executor, and customer-first.” But his expectations for his team are just as clear. Modern marketers, in his view, must be commercially savvy — not just creative or data-fluent.

Certainly, he has helped reshape the culture and cadence of marketing at MYOB, moving it from a transactional ticketing system to a strategic, empowered function with clear direction and purpose.

“Following the marketing organisation coming together we were able to record our baseline engagement of 56 per cent – not great. Over the course of 12 months, we were able to increase this to 77 per cent. We weren’t good at being  organised, communicating how we make decisions, and how marketing collaborated across the company. We had to change, and we did.”

When the unified marketing organisation was first established, employee engagement sat at just 56 per cent. A year later, that figure rose to 77 per cent. The turnaround wasn’t accidental. It came from investing in the fundamentals: clearer communication, better decision-making processes, more in-person connection points, and a genuine focus on learning, development, and craft. The numbers tell the story — decision-making confidence up 26 per cent, belief that action will follow up 21 per cent, teamwork and collaboration up 13 per cent, and L&D favourability at 84 per cent.

The shift was driven by an energised senior leadership team and a clear mandate for marketing’s role in the business. Everyone across the function completed their Clifton Strengths profile and participated in workshops, adopting a shared language to better understand how individuals and teams collaborate.

Two major talent programs were launched to support this people-first vision. The Aspiring Leaders Program enrolled 13 future leaders in a 12-month journey combining external learning with mentorship from senior MYOB leaders. In parallel, 34 high performers were invited into a dedicated High Performance Program, designed to accelerate capability and connection among MYOB’s top marketing talent.

Certainly, Chadwick leads with openness, clarity, and support. The result? Senior leadership engagement is at 90 per cent, and 48 out of 64 survey questions received a 100 per cent favourable response.

It’s a people-first, performance-driven culture – and under Chadwick’s leadership, it’s built to last.