Head of Product Engineering & AI

About H&L

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.

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

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.

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.

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

• Own the end-to-end product and platform strategy and roadmap
• Drive product discovery and validation through structured customer research, rapid prototyping, and market testing
• Oversee the full product lifecycle from ideation through commercialisation and scaling, with a clear prioritisation framework
• Set strategic objectives and measurable success metrics for all product initiatives
• Balance the evolution of the core platform with client-specific custom development
• Establish capacity visibility across the product and engineering pipeline so that client commitments are made with confidence and delivery delays become the exception
• 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

• Build working product solutions using AI as the primary execution medium, moving from problem framing to working solution without reliance on legacy SDLC rituals
• Rapidly prototype, iterate, and refine solutions to validate ideas early
• 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
• Leverage AI across the full development loop (requirements analysis, design exploration, implementation, and testing) to move faster and with greater precision
• Identify and develop new revenue streams driven by AI capabilities, evaluated on impact, feasibility, and learning velocity

3. Customer Engagement & Commercial Validation

• Engage directly with hospitality customers to understand operational challenges and validate product assumptions
• Measure and report on adoption, satisfaction, and commercial impact of new features
• Support pricing and packaging strategies for product offerings in partnership with Sales and the Managing Director

4. AI Innovation Lead Across the Organisation

• Lead the cultural shift toward AI-first thinking across the organisation: this is about fundamentally changing how people work, make decisions, and solve problems
• 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
• Partner with team leaders across the business to set function-specific AI adoption goals, track progress, and create accountability

5. Internal AI Transformation

• Audit business functions for high-value automation opportunities and prioritise by impact, feasibility, and learning velocity
• Build and deploy working AI agents and automated workflows that eliminate repetitive manual work. Not plans or recommendations, but live solutions.
• Build AI capability across teams through hands-on enablement
• Define clear success metrics for every internal AI initiative across the business; report measurable outcomes

6. Cross-Functional AI Leadership & Organisational Alignment

• Act as the bridge between executive direction and ground-level product and engineering execution
• Collaborate closely with all functions to maintain alignment on product direction and delivery commitments
• Align teams around clearly defined AI business outcomes; influence through credibility, evidence, and shipped results rather than hierarchy
• Communicate product and AI strategy clearly and regularly to all stakeholders
• Represent H&L externally in discussions relating to product capability and AI innovation

7. People & Team Leadership

• Build, lead, and mentor high-performing product and engineering teams, instilling a culture of ownership, experimentation, and customer-centricity
• Hire, develop, and retain product and engineering talent; build a team capable of scaling with the Company’s ambitions
• Set clear performance expectations, conduct regular reviews, and actively support career development and progression
• Operate as a founder-like leader: take accountability for outcomes from ideation through to scale

What This Role Is Not

To set clear expectations:

• Not a backlog or roadmap-only role. This role builds, ships, and measures.
• Not a handoff-based product manager. Requirements do not get thrown over the fence to engineering
• Not a requirements writer detached from execution. You move from problem understanding to working solution
• Not an AI theorist or strategist disconnected from commercial impact. Every initiative must demonstrate measurable value
• 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
• Not a passenger on the technology shift. You are leading it
• This is a business transformation role with full commercial accountability. Bias toward action is non-negotiable

Required Skills & Experience

Background

• Started your career in software engineering and worked as an engineer for at least 3 years before moving into product leadership
• 8+ years combined across engineering and product, with at least 4 years leading product or product engineering teams in B2B SaaS or enterprise software
• You still write code. You use modern AI coding tools (Claude Code, Codex, Cursor, or equivalents) as part of your daily work. You can show us what you have built recently
• You have led engineering teams through a platform modernisation or technology shift, including environments with legacy or on-premise constraints

Technical & AI Capability

• Demonstrated ability to design, prototype, and ship working AI-enabled solutions in a commercial environment.
• Strong understanding of modern software architecture, APIs, cloud services, and AI/ML technologies and their practical applications
• Experience with agentic workflows, automation tooling, and AI governance frameworks
• Ability to think across systems, integrate multiple workflows, and engage engineering teams with precision

Product & Commercial Acumen

• Experience managing both a core product roadmap and client-specific custom development, with the discipline to balance and prioritise across both
• Strong commercial instincts: you build business cases, deprioritise low-ROI work
• Familiarity with hospitality technology, POS systems, or adjacent verticals is an advantage
• Experience driving operational or digital transformation initiatives with measurable commercial outcomes

Leadership & Communication

• Proven ability to drive change in established environments and influence across functions without formal authority
• Able to write a tight spec, run a sprint, hold engineering accountable to timelines, and communicate clearly to clients and executives
• Experience engaging directly with customers or end users; ability to explain AI systems clearly and responsibly
• Strong bias toward action: you ship things, measure them, and improve based on what you learn

Success Profile

The successful candidate will be:

• Commercially pragmatic and outcome-driven, motivated by measurable improvement rather than theoretical innovation
• Technically fluent yet business-focused, comfortable moving between a customer conversation and an engineering spec
• A confident decision-maker in environments with ambiguity and competing priorities
• Comfortable working across functional boundaries and influencing senior stakeholders
• A hands-on leader who models the bias toward action they expect from their team
• 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

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.

The role offers:

• Direct access to and support from the Managing Director and leadership team
• Real organisational scope: both product and internal transformation sit within this mandate
• A global customer base and a platform with decades of domain depth to build on
• A small, senior team where your decisions have outsized impact
• Competitive compensation and the opportunity to shape how AI is embedded across an entire operating model

#AspireSoftware #H&L