Introduction About Us At Prevail, we believe success isn’t given, it’s built. We stand alongside discerning customers to protect what they’ve created in life and business; with the same care and commitment they put into building it. We deliver crafted insurance solutions across niche segments: High Net Worth, Specialty (specialised small business), and Lifestyle & Leisure. These are customers with unique and complex needs, and we design coverage that fits, removes friction, and takes risk off their plate. Everything we do aims at the best experience and the best outcome for the end customer: clear processes, fast decisions, reliable coverage, and measurable results. We act with integrity, own our outcomes, and get 1% better every day, progressive, energetic, and forward-thinking by design About the Opportunity As the Head of Operations your role is about lifting the performance, maturity, and rhythm of our business building an operation that’s sharper, faster, and easier to scale. It leads our core operating functions business operations, technology platforms, offshoring, and operational compliance to deliver consistently high standards for brokers, partners, and customers. Reporting directly to the CEO, this role ensures our service engine and technology backbone run as one, creating the foundation for long-term growth and scalability. Key Responsibilities Operational Leadership – Lead and coordinate all core operational functions across underwriting support, service delivery, and workflow improvement. Technology & Platform Oversight – Work with our BA team and vendors to enhance system performance, simplify processes, and ensure tech aligns with strategic priorities. Operational Compliance – Oversee the operational compliance function, ensuring strong governance, insurer reporting, and adherence to authority frameworks. Offshore Team Management – Lead and support our Manila-based team as a fully integrated extension of our business, maintaining performance and cultural alignment. Data-Driven Operations – Use data insights to monitor daily performance, turnaround times, error rates, and rework; partner with data teams to continually improve service outcomes. Process & Performance Improvement – Identify and remove friction across workflows, embed automation, and lift the maturity and consistency of how we operate. Expense & Vendor Management – Maintain expense discipline, ensuring operational and platform costs remain within budget. Leverage procurement and group partnerships to secure cost efficiency and delivery excellence. Workplace & Culture – Ensure the physical and digital workplace supports collaboration, brand presence, and employee engagement. Continuous Improvement – Embed a mindset of ongoing optimisation, ensuring both employee and customer experiences improve with every iteration. Skills and Qualifications Minimum 10 years’ experience in underwriting, insurance operations, or broader financial services, with a proven track record in operational leadership. Demonstrated experience leading end-to-end operational functions within an underwriting or insurance environment. Strong capability in operational improvement, process optimisation, and change management. Proven experience as a senior operations leader or head of function, ideally within an underwriting agency or insurer. Solid understanding of underwriting systems, technology platforms, and digital transformation initiatives that drive operational efficiency and scalability. Strong commercial acumen with experience in budgeting, forecasting, and financial performance management. Exceptional communication, negotiation, and stakeholder management skills, with the ability to influence and build alignment across senior levels. Advanced problem-solving and analytical abilities with a focus on continuous improvement and data-driven decision-making. In-depth knowledge of industry regulations, compliance standards, and risk management practices relevant to underwriting operations. Benefits As a valued member of Prevail, we believe that when people thrive, performance follows. That’s why we’ve built a benefits offering that supports your wellbeing, growth, protection, and purpose—not just at work, but in life. We back our team with real flexibility, meaningful development, and a culture where accountability, integrity, and contribution matter We believe in hybrid working, purposeful time together to build strong connections, spark ideas and move faster, while giving you the space and flexibility to focus and perform at your best. You’ll grow through structured development, mentoring and tuition support, with ANZIIF accreditation pathways that convert learning into real capability. You're backed by company-paid Life, TPD, Salary Continuance and Travel insurance, with access to additional discounted cover. Your wellbeing is supported through annual health checks, skin checks, flu shots, holistic wellness programs and confidential counselling. You’ll thrive in a collegiate, high-trust culture where integrity and accountability matter, your ideas land quickly, and your contribution counts. Why Join Prevail This is more than a role it’s your chance to help shape one of Australia’s most forward-thinking specialist underwriting agencies. At Prevail, you’ll work on complex, meaningful risks across High Net Worth, Specialty, Lifestyle & Leisure for customers who expect more and value precision. You’ll be part of a high-performance, no-ego culture where ideas move fast, ownership is real, and the team succeeds together. We’re modernising how we work from better systems and digital platforms to refreshed, purpose-built office spaces designed to energise and connect. And we back what matters to you with volunteer leave, a genuine focus on wellbeing, and a working rhythm that supports both your ambition and your life. If you’re ready to grow with a business that’s moving fast, shape something meaningful, and help set a new benchmark for what great looks like in specialist insurance — this is your moment. Our Culture & Values At Prevail, our values aren’t just words they’re behaviours we live every day. They guide how we work, how we show up for each other, and how we deliver results. P – Problem-Solving We lean into challenges with creativity, energy, and action. R – Relationships We build trust through genuine connection and shared success. E – Easy to Deal With We make life easier for customers, partners, and colleagues. V – Value We focus on what matters and deliver with integrity. A – Accountability We take responsibility and follow through — no excuses. I – Integrity We do the right thing — even when no one’s watching. L – Learning We challenge ourselves to improve — every day, in every way. To Apply We are always on the lookout for great talent, if you are interested in a confidential conversation regarding career opportunities, please email talent@steadfast.com.au We believe that our people are our greatest asset. Our people are chosen for their personalities, their ethics and professional qualities without any exclusion, preferential treatment, or discrimination. We are proud to be an equal opportunities employer and do not discriminate by reason of age, gender, gender identity, race, sexual orientation, nationality, religion or disability or any other difference. We encourage applications from all individuals and will provide appropriate assistance for candidates with disabilities or special needs throughout the recruitment process upon request.
