Head of Technology & Product

About FreightSafe

FreightSafe specializes in risk and claims management at the nexus of logistics, risk control, and technology. We develop and oversee self-funded warranty schemes for transport companies across Australia, handling thousands of claims annually. Our approach leverages technology, data, and creativity, enhancing our models and client outcomes with every claim and insight uncovered. Unlike traditional insurers or claims processors, we create tailored solutions that scale for Australia's major transport firms. Currently, we are experiencing significant commercial expansion, powered by technology, with this role central to that growth.

Role Overview

We seek a Head of Technology & Product to join our Executive Leadership Team, someone who envisions novel possibilities for technology within our business. This senior leader will oversee the development of a next-gen agentic claims management platform, replacing a 12-year-old system and adopting modern infrastructure with effective AI use beyond marketing claims.

Reporting directly to the CEO, this individual will manage a team of four engineers and collaborate closely with commercial leaders and key clients, including external stakeholders like FreightInsure, to ensure technology drives tangible business impact. They will also steward FreightSafe’s valuable data assets to create competitive advantages internally and externally.

Key Responsibilities

• Lead the construction and deployment of the new agentic claims management platform, partnering with third-party developers transitioning ownership in-house and evolving the engineering team onto this platform.
• Define the technical vision, ensuring scalability and longevity of the system.
• Design AI agents to automate claims processes such as triage, assessment, communications, and reporting, increasing efficiency and cutting manual tasks.
• Manage all technical and infrastructure decisions across the business.
• Ensure excellent user experiences for internal staff (claims, operations, commercial teams) and external users (clients, insurers).
• Convert commercial needs into product features and align product roadmap with business objectives and technical feasibility.
• Maintain live product roadmaps reflecting priorities and capabilities.
• Manage FreightSafe’s data portfolio—including claims, loss patterns, carrier behaviors, and risk profiles—and construct data products that provide client value and position the company as a sector authority.
• Apply agentic AI and advanced tools to uncover insights formerly requiring manual analysis.
• Expand AI usage throughout operations, client interactions, compliance, and reporting, while upholding responsible, auditable frameworks meeting governance and regulatory standards.
• Remove manual processes through automation without sacrificing quality or oversight.
• Lead, mentor, and grow a team of four engineers and analysts, fostering a culture of accountability, continuous learning, and care.
• Serve as a key voice on the Executive Leadership Team, contributing insights on technology, data strategy, and operational efficiency.

Candidate Profile

The ideal candidate combines deep technical expertise, commercial savvy, and exemplary interpersonal skills. They should bring minimum five years in senior technology roles, preferably where technology served as the core product rather than a supporting asset. A working knowledge of agentic systems, modern data infrastructure, and pragmatic AI application is essential, along with the ability to engage effectively with engineers and commercial stakeholders alike. High emotional intelligence, humility, direct communication, and team-building focus are vital. Industry experience in logistics, insurance, fintech, or regulated sectors is advantageous but not essential; a visionary mindset is paramount.

What We Offer

• Participation in the Executive Leadership Team with significant influence on company direction.
• Opportunity within a well-funded, commercially operational growth phase, past product-market fit and scaling up.
• Mandate to innovate and build impactful solutions, not just manage existing ones.
• Collaborative, low-ego leadership culture emphasizing clear communication and shared accountability.
• Competitive salary aligned with role seniority and breadth.
• Hybrid working model based in Sydney.