Head of CX Automation, AI

Holafly

Leading AI and automation strategy for Holafly's customer experience. Championing traveler journeys and mentoring a high-impact team to ensure seamless connectivity.

Posted 7/27/2026full-timeRemote • 🇮🇪 IrelandLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in AI and automation strategy within customer experience, focusing on conversational AI, automation architecture, and vendor management. Proven ability to lead and develop technical teams while optimizing complex data workflows and ensuring high-quality user interactions.

Highest-signal resume keywords

AI Strategy DevelopmentNLP MasteryConversational ArchitectureVendor Relationship ManagementTeam Leadership and Upskilling

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

LLM DeploymentChatbot DevelopmentAI-Driven AutomationPrompt EngineeringData Workflow OptimizationCX Metrics TrackingIncident ManagementAutomation ArchitectureContext-Driven Human-Agent FallbackConversational Platform Optimization

Soft Skills

CoachingCommunicationCollaborationProblem-SolvingLeadership

Tools & Technologies

CX PlatformsAgent Assist ToolsQA Automation ToolsAI Technology Providers

Industry Keywords

Customer ExperienceAI GovernanceData PrivacyEU AI ActSLA Management

About the role

Key responsibilities & impact

Own and scale Holafly's AI and automation strategy across the entire CX landscape, spanning both customer-facing and agent-facing experiences, identifying and prioritizing high-impact opportunities to embed conversational AI and automation into key user journeys, not limited to any single tool or channel.
Lead the team's roadmap and project planning, prioritizing initiatives and resourcing; collaborate with Product and Project Managers when they lead specific initiatives that require this team's execution.
Lead and grow an elite AI & Automation team (currently [X people]), including working closely with the team's current manager as part of the broader team, building on the team's strengths, and raising the technical bar in engineering practices, automation architecture, and AI implementation.
Architect and continuously refine the CX automation infrastructure, from chatbot and CX platform to agent-facing tools (e.g., agent assist, QA automation), ensuring frictionless, context-rich handovers between bots and human agents.
Track and act on essential CX and automation metrics on a regular basis, including CCR (containment rate), deflection rate, escalation rate, FCR, CSAT, drop-off rate, repeat contact rate, and intent recognition accuracy, combining quantitative interaction logs and qualitative Voice of Customer insights to proactively eliminate journey friction.
Report on cost-per-contact and containment-driven savings as the business outcome of this work, alongside quality trade-offs, to leadership.
Establish robust AI governance frameworks aligned with data privacy, responsible AI practices, and international regulatory baselines like the EU AI Act.
Own incident management across the CX automation stack, covering both technical issues (outages, bugs) and customer-impacting incidents (e.g., problematic automated responses), ensuring fast triage, resolution, and clear communication.
Own the relationship with CX platform and AI technology providers, managing vendor performance, contract and commercial terms, product roadmap influence, and escalations, and evaluating vendor fit as the business evolves.
Act as a hands-on AI advisor and stakeholder on self-service and cross-functional initiatives led by Product, IT, and Customer Journeys teams, ensuring AI strategy stays consistent and high-quality across the entire CX ecosystem, even where execution sits outside this team.

Requirements

What you’ll need

Proven track record of defining, deploying, and scaling sophisticated LLM, chatbot, and AI-driven automation projects across a broad CX ecosystem, in live production environments.
Demonstrated experience leading and upskilling technical teams, someone who can coach and elevate capability, not just direct.
Deep technical mastery of NLP, prompt engineering, complex data workflows, and conversational architecture, with the ability to translate that expertise into practical guidance for the team.
Expertise in conversational platform optimization, agent-facing AI tools, and context-driven human-agent fallback loops.
Experience managing technology vendor relationships, including commercial negotiations and holding providers accountable to SLAs and roadmap commitments.

Benefits

Comp & perks

100% remote flexibility, open to candidates based in EMEA, Northern Europe, or Africa.
Flexible working hours that support work-life balance and well-being.
Real ownership and autonomy to shape the technical future of a global market leader.