About H&LH;&L; POS (Hospitality & Leisure) is a leading provider of point-of-sale and integrated business management solutions purpose-built for the hospitality and food & beverage sectors.
With more than 30 years of industry experience, H&L; delivers flexible POS, back-of-house, inventory, workforce management and reporting systems that help hotels, pubs, restaurants, bars, clubs, cafés, liquor retailers and event venues operate efficiently and profitably.Our platform connects front-of-house sales with stock control and data management, supports online ordering, table service, reservations and advanced reporting, and integrates with more than 150 hospitality technology partners.
H&L;'s customer-centric approach and deep sector expertise enable operators to focus on delivering exceptional guest experiences while maintaining visibility, control and sustainable growth across their businesses.The OpportunityH&L; is entering its next phase of growth.
As a well-established hospitality technology provider with a strong customer base and a respected product suite, we have a significant opportunity to modernize how we operate and compete, and AI is at the center of that ambition.We are seeking a senior, hands‐on product and AI leader to own both the evolution of our product platform and the practical integration of AI across the business.
This is not a research or advisory role.
It is a dual mandate: build and ship products that customers value and pay for, and deploy AI in ways that make H&L; measurably faster, leaner, and more competitive.The Head of Product & AI Innovation Lead will work directly with the Managing Director and the leadership team to drive product strategy, validate and launch AI‐powered features, redesign internal workflows, and deliver tangible business outcomes.
Success in this role is measured by impact: product adoption, customer retention, margin improvement, and faster execution across the organization.Key Responsibilities1.
Product Strategy & RoadmapOwn the end-to-end product strategy and roadmap, aligned with company objectivesDrive product discovery and validation through structured customer research, rapid prototyping, and market testingOversee the full product lifecycle from ideation through commercialization and scaling, with a clear prioritization frameworkSet strategic objectives and measurable success metrics for all product initiativesBalance the evolution of the core platform with client‐specific custom developmentEstablish capacity visibility across the product and engineering pipeline so that client commitments are made with confidence and delivery delays become the exception2.
AI‐Powered Product DevelopmentBuild working product solutions using AI as the primary execution medium, moving from problem framing to working solution without reliance on legacy SDLC ritualsRapidly prototype, iterate, and refine solutions to validate ideas earlyConduct 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 developmentLeverage AI across the full development loop (requirements analysis, design exploration, implementation, and testing) to move faster and with greater precisionIdentify and develop recent revenue streams driven by AI capabilities, evaluated on impact, feasibility, and learning velocity3.
Customer Engagement & Commercial ValidationEngage directly with hospitality customers to understand operational challenges and validate product assumptionsMeasure and report on adoption, satisfaction, and commercial impact of new featuresSupport pricing and packaging strategies for product offerings in partnership with Sales and the Managing Director4.
AI Innovation Lead Across the OrganizationLead the cultural shift toward AI‐first thinking across the organization: this is about fundamentally changing how people work, make decisions, and solve problemsEstablish 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 arePartner with team leaders across the business to set function‐specific AI adoption goals, track progress, and create accountability5.
Internal AI TransformationAudit business functions for high‐value automation opportunities and prioritize by impact, feasibility, and learning velocityBuild 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 enablementDefine clear success metrics for every internal AI initiative across the business; report measurable outcomes6.
Cross‐Functional AI Leadership & Organizational AlignmentAct as the bridge between executive direction and ground‐level product and engineering executionCollaborate closely with all functions to maintain alignment on product direction and delivery commitmentsAlign teams around clearly defined AI business outcomes; influence through credibility, evidence, and shipped results rather than hierarchyCommunicate product and AI strategy clearly and regularly to all stakeholdersRepresent H&L; externally in discussions relating to product capability and AI innovation7.
People & Team LeadershipBuild, lead, and mentor a high‐performing product team, instilling a culture of ownership, experimentation, and customer‐centricityHire, develop, and retain product talent; build a team capable of scaling with the Company's ambitionsSet clear performance expectations, conduct regular reviews, and actively support career development and progressionOperate as a founder‐like leader:



take accountability for outcomes from ideation through to scaleWhat This Role Is NotNot 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 engineeringNot a requirements writer detached from execution.
You move from problem understanding to working solutionNot an AI theorist or strategist disconnected from commercial impact.
Every initiative must demonstrate measurable valueThis is a business transformation role with full commercial accountability.
Bias toward action is non‐negotiableRequired Skills & ExperienceTechnical & AI CapabilityDemonstrated 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 applicationsExperience with agentic workflows, automation tooling, and AI governance frameworksAbility to think across systems, integrate multiple workflows, and engage engineering teams with precisionProduct & Commercial Acumen8+ years in product management or product leadership in B2B SaaS or enterprise softwareExperience managing both a core product roadmap and client‐specific custom development, with the discipline to balance and prioritize across bothStrong commercial instincts: you build business cases, deprioritize low‐ROI workFamiliarity with hospitality technology, POS systems, or adjacent verticals is an advantageExperience driving operational or digital transformation initiatives with measurable commercial outcomesLeadership & CommunicationProven ability to drive change in established environments and influence across functions without formal authorityAble to write a tight spec, run a sprint, hold engineering accountable to timelines, and communicate clearly to clients and executivesExperience engaging directly with customers or end users; ability to explain AI systems clearly and responsiblyStrong bias toward action: you ship things, measure them, and improve based on what you learnSuccess ProfileCommercially pragmatic and outcome‐driven, motivated by measurable improvement rather than theoretical innovationTechnically fluent yet business‐focused, comfortable moving between a customer conversation and an engineering specA confident decision‐maker in environments with ambiguity and competing prioritiesComfortable working across functional boundaries and influencing senior stakeholdersA hands‐on leader who models the bias toward action they expect from their teamWhy Join HAI 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 teamReal organizational scope: both product and internal transformation sit within this mandateA global customer base and a platform with decades of domain depth to build onA small, senior team where your decisions have outsized impactCompetitive compensation and the opportunity to shape how AI is embedded across an entire operating model
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📌 Head Of Product And Ai Innovation (Sydney)
🏢 Valsoft Corporation
📍 Sydney