Matt Fairhurst, co-founder and CEO of Skedulo, shares the journey of building one of Australia’s most successful under-the-radar tech companies. From a small-town upbringing in Queensland to leading an enterprise SaaS company that powers deskless workers worldwide, Matt’s story is one of creativity, adaptability, and leadership. He discusses his transition from music and graphic design into tech, the early days of Skedulo, and the evolution of the product to serve mission-critical operations across healthcare, field services, and beyond. Matt reflects on scaling globally, navigating U.S. expansion, raising venture capital, and steering Skedulo through the pandemic where the company played a pivotal role in COVID testing and vaccination scheduling. His insights into culture, leadership, and founder dynamics provide valuable lessons for entrepreneurs at any stage. This episode is essential listening for anyone building in enterprise SaaS, workforce management, or scaling a startup internationally.

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Matt Fairhurst’s journey into tech entrepreneurship began in an unlikely place: a small town in Queensland, Australia. Raised in a disciplined but conservative household, Matt was always drawn to creativity and problem-solving. His early interests in music and graphic design led him to self-teach web development, a skill that later became instrumental in his career.

After university, Matt took on various marketing and design roles which exposed him to different industries. He eventually landed in the Salesforce consulting space where he met his future co-founder, James. Together, they built an internal product that addressed the inefficiencies of scheduling and managing deskless workers. When their consulting company was acquired, the acquirers weren’t interested in their product—but Matt and James saw its potential. They spun it out as Skedulo.

The early days of Skedulo were intense. With no background in venture capital, Matt initially struggled to raise funds, even mistaking a non-relevant website for Blackbird Ventures when first introduced to them. However, by focusing on customer traction and the real-world pain points Skedulo was solving, they secured Blackbird’s investment in 2014. This marked the beginning of Skedulo’s growth from an Australian startup into a global SaaS company.

Skedulo’s core value proposition is optimizing how companies manage deskless workers—people who operate outside of traditional office environments such as healthcare professionals, field service technicians, and mobile workforces. Unlike existing solutions which were either too rigid or designed for specific industries, Skedulo aimed to be a flexible platform that could serve a broad range of companies.

As Skedulo scaled, Matt navigated the complexities of expanding into the U.S., establishing a presence in North America to access larger markets and enterprise customers. He reflects on the cultural differences, the importance of hiring the right talent, and the challenges of managing a global team. Despite early struggles, Skedulo gained traction with major clients including healthcare organizations and enterprise service providers.

Then came COVID-19. The pandemic created both a crisis and an opportunity for Skedulo. Many of their customers in field services paused operations but healthcare and government organizations needed urgent scheduling solutions for COVID testing and vaccinations. Recognizing the importance of the moment, Matt and his team rapidly built a scheduling system for mass testing and vaccine administration, partnering with governments and agencies worldwide. This accelerated Skedulo’s impact and growth, positioning it as a critical infrastructure player during the pandemic.

Beyond product and scaling challenges, Matt delves into leadership and company culture. He emphasizes the role of founders in shaping an organization’s DNA, the evolution of company values as a team grows, and the necessity of adjusting leadership styles at different stages. He also touches on the importance of resilience, staying calm under pressure, and continuously evolving to meet market demands.

Looking ahead, Matt envisions Skedulo evolving into a platform that not only manages workforce logistics but also enhances training, engagement, and overall job satisfaction for deskless workers. His advice to founders? Define your core values early, stay adaptable, and always be prepared to evolve both personally and as a company.

This episode is packed with insights on enterprise SaaS, international expansion, and leadership through crisis, making it essential listening for startup founders, investors, and business leaders.

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