Head of Product and AI Innovation

About H&L

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.

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 Opportunity

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.

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 Responsibilities

1. Product Strategy & Roadmap

• Own the end-to-end product strategy and roadmap, aligned with company objectives
• Drive product discovery and validation through structured customer research, rapid prototyping, and market testing
• Oversee the full product lifecycle from ideation through commercialization and scaling, with a clear prioritization 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

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 Organization

• Lead the cultural shift toward AI-first thinking across the organization: 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 prioritize 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 & Organizational 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 a high-performing product team, instilling a culture of ownership, experimentation, and customer-centricity
• Hire, develop, and retain product 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
• This is a business transformation role with full commercial accountability. Bias toward action is non-negotiable

Required Skills & Experience

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

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

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 organizational 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

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