Job Description
Description
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About H&L;
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H&L; is a leading hospitality technology platform serving the food & beverage and hospitality sectors across Australia and New Zealand. With more than 30 years of industry experience, H&L; delivers an integrated platform spanning commerce, payments, operations, inventory, workforce management and reporting that helps hotels, pubs, restaurants, bars, clubs, cafes, liquor retailers and event venues operate efficiently and profitably.
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Our platform aggregates transactions across every sale point (terminal, mobile, QR, online ordering, and increasingly voice and agentic channels), connects front-of-house commerce with back-of-house operations, advanced reporting, and integrates with more than 150 hospitality technology partners. H&L;'s deep sector expertise enables operators to focus on delivering exceptional guest experiences while we focus on the platform underneath that makes it possible.
The Opportunity
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H&L; is entering its next phase of growth. We have a strong customer base, deep sector expertise, and decades of platform capability behind us. The work ahead is to modernise the technology, sharpen how we operate as a hospitality platform, and make AI core to how we build and what we ship.
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We are seeking a senior, hands-on technical leader who came up through engineering and grew into product leadership. This is not a research, strategy, or advisory role. It is a dual mandate: lead the platform forward technically while shipping AI-powered products and capabilities that customers value and pay for, and that make H&L; measurably faster, leaner, and more competitive.
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The Head of Product Engineering & AI will work directly with the Managing Director and leadership team to set platform direction, lead engineering through a meaningful technology shift, validate and launch AI-powered features, redesign internal workflows, and deliver tangible business outcomes. Success is measured by impact: product adoption, customer retention, margin improvement, and faster execution across the organisation.
Key Responsibilities
1. Product Strategy & Roadmap
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• Own the end-to-end product and platform strategy and roadmap
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• Drive product discovery and validation through structured customer research, rapid prototyping, and market testing
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• Oversee the full product lifecycle from ideation through commercialisation and scaling, with a clear prioritisation framework
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• Set strategic objectives and measurable success metrics for all product initiatives
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• Balance the evolution of the core platform with client-specific custom development
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• Establish capacity visibility across the product and engineering pipeline so that client commitments are made with confidence and delivery delays become the exception
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• Make architecture and build/partner/AI delivery decisions that balance commercial outcomes, technical debt, and constraints of an on-premise footprint. Lead the team through a sustained technology shift without sacrificing velocity to customers today.
2. AI-Powered Product Development
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• Build working product solutions using AI as the primary execution medium, moving from problem framing to working solution without reliance on legacy SDLC rituals
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• Rapidly prototype, iterate, and refine solutions to validate ideas early
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• Conduct structured discoveries with customers to identify the highest-value opportunities; build a clear business case quantifying revenue uplift, cost savings, or retention impact before committing to development
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• Leverage AI across the full development loop (requirements analysis, design exploration, implementation, and testing) to move faster and with greater precision
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• Identify and develop new revenue streams driven by AI capabilities, evaluated on impact, feasibility,



and learning velocity
3. Customer Engagement & Commercial Validation
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• Engage directly with hospitality customers to understand operational challenges and validate product assumptions
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• Measure and report on adoption, satisfaction, and commercial impact of new features
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• Support pricing and packaging strategies for product offerings in partnership with Sales and the Managing Director
4. AI Innovation Lead Across the Organisation
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• Lead the cultural shift toward AI-first thinking across the organisation: this is about fundamentally changing how people work, make decisions, and solve problems
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• Establish clear expectations for AI adoption and embedding AI into day-to-day operating processes across every function and create practical enablement programs that meet people where they are
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• Partner with team leaders across the business to set function-specific AI adoption goals, track progress, and create accountability
5. Internal AI Transformation
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• Audit business functions for high-value automation opportunities and prioritise by impact, feasibility, and learning velocity
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• Build and deploy working AI agents and automated workflows that eliminate repetitive manual work. Not plans or recommendations, but live solutions.
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• Build AI capability across teams through hands-on enablement
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• Define clear success metrics for every internal AI initiative across the business; report measurable outcomes
6. Cross-Functional AI Leadership & Organisational Alignment
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• Act as the bridge between executive direction and ground-level product and engineering execution
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• Collaborate closely with all functions to maintain alignment on product direction and delivery commitments
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• Align teams around clearly defined AI business outcomes; influence through credibility, evidence, and shipped results rather than hierarchy
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• Communicate product and AI strategy clearly and regularly to all stakeholders
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• Represent H&L; externally in discussions relating to product capability and AI innovation
7. People & Team Leadership
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• Build, lead, and mentor high-performing product and engineering teams, instilling a culture of ownership, experimentation, and customer-centricity
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• Hire, develop, and retain product and engineering talent; build a team capable of scaling with the Company's ambitions
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• Set clear performance expectations, conduct regular reviews, and actively support career development and progression
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• Operate as a founder-like leader: take accountability for outcomes from ideation through to scale
What This Role Is Not
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To set clear expectations:
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• Not a backlog or roadmap-only role. This role builds, ships, and measures.
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• Not a handoff-based product manager. Requirements do not get thrown over the fence to engineering
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• Not a requirements writer detached from execution. You move from problem understanding to working solution
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• Not an AI theorist or strategist disconnected from commercial impact. Every initiative must demonstrate measurable value
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• Not a non-technical product leader. You have engineering depth, have shipped production code, and can hold your own in architecture, code review, and trade-off conversations with senior engineers
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• Not a passenger on the technology shift. You are leading it
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• This is a business transformation role with full commercial accountability. Bias toward action is non-negotiable
Required Skills & Experience
Background
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• Started your career in software engineering and worked as an engineer for at least 3 years before moving into product leadership
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• 8+ years combined across engineering and product, with at least 4 years leading product or product engineering teams in B2B SaaS or enterprise software
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• You still write code. You use up-to-date AI coding tools (Claude Code, Codex, Cursor, or equivalents) as part of your daily work. You can show us what you have built recently
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• You have led engineering teams through a platform modernisation or technology shift, including environments with legacy or on-premise constraints
Technical & AI Capability
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• Demonstrated ability to design, prototype, and ship working AI-enabled solutions in a commercial environment.
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• Strong understanding of modern software architecture, APIs, cloud services, and AI/ML technologies and their practical applications
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• Experience with agentic workflows, automation tooling, and AI governance frameworks
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• Ability to think across systems, integrate multiple workflows, and engage engineering teams with precision
Product & Commercial Acumen
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• Experience managing both a core product roadmap and client-specific custom development, with the discipline to balance and prioritise across both
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• Strong commercial instincts: you build business cases, deprioritise low-ROI work
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• Familiarity with hospitality technology, POS systems, or adjacent verticals is an advantage
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• Experience driving operational or digital transformation initiatives with measurable commercial outcomes
Leadership & Communication
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• Proven ability to drive change in established environments and influence across functions without formal authority
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• Able to write a tight spec, run a sprint, hold engineering accountable to timelines, and communicate clearly to clients and executives
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• Experience engaging directly with customers or end users; ability to explain AI systems clearly and responsibly
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• Strong bias toward action: you ship things, measure them, and improve based on what you learn
Success Profile
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The successful candidate will be:
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• Commercially pragmatic and outcome-driven, motivated by measurable improvement rather than theoretical innovation
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• Technically fluent yet business-focused, comfortable moving between a customer conversation and an engineering spec
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• A confident decision-maker in environments with ambiguity and competing priorities
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• Comfortable working across functional boundaries and influencing senior stakeholders
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• A hands-on leader who models the bias toward action they expect from their team
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• Comfortable making architecture and product trade-offs publicly: you explain the call, name what you are giving up, and bring the team with you
Why Join H&L;
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This is an opportunity to lead a meaningful transformation within a well-established hospitality technology business at a genuine inflection point. AI has changed what is possible in how software is built, what it can do for end users, and how businesses like H&L; can operate.
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The role offers:
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• Direct access to and support from the Managing Director and leadership team
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• Real organisational scope: both product and internal transformation sit within this mandate
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• A global customer base and a platform with decades of domain depth to build on
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• A small, senior team where your decisions have outsized impact
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• Competitive compensation and the opportunity to shape how AI is embedded across an entire operating model
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#AspireSoftware #H&L;

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