Head of Product Engineering & AI

Job Description

Overview

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H&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.

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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.

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The Opportunity

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H&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.

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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.

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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.

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Key Responsibilities

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• Product Strategy & Roadmap\n
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  • Own the end-to-end product strategy and roadmap, aligned with company objectives
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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 commercialization and scaling, with a clear prioritization 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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• AI-Powered Product Development\n
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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
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• Customer Engagement & Commercial Validation\n
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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
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• AI Innovation Lead Across the Organization\n
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  • Lead the cultural shift toward AI-first thinking across the organization: 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
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• Internal AI Transformation\n
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  • Audit business functions for high-value automation opportunities and prioritize 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
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• Cross-Functional AI Leadership & Organizational Alignment\n
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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
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• People & Team Leadership\n
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  • Build, lead, and mentor a high-performing product team, instilling a culture of ownership, experimentation, and customer-centricity
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  • Hire, develop, and retain product 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
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What This Role Is Not

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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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• This is a business transformation role with full commercial accountability. Bias toward action is non-negotiable
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Required Skills & Experience

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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
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Product & Commercial Acumen

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• 8+ years in product management or product leadership in B2B SaaS or enterprise software
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• Experience managing both a core product roadmap and client-specific custom development, with the discipline to balance and prioritize across both
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• Strong commercial instincts: you build business cases, deprioritize 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
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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
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Success Profile

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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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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 organizational 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