Head of CX Automation & AI

Company Overview

Holafly is a high-growth scale-up revolutionising how businesses and travellers connect to the internet abroad. Since 2018, we’ve empowered travellers in over 200 destinations worldwide with secure and reliable eSIM solutions. With a team of 500+ professionals across multiple countries, we are scaling globally to support travellers with seamless, unlimited data connectivity.

We’re not just connecting people-we’re enabling freedom and peace of mind, ensuring our users stay connected from the second they land, wherever their journey takes them.

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As the Head of CX Automation & AI, own and scale the comprehensive AI and automation strategy across the CX landscape, refining current infrastructures while uncovering high-impact opportunities to embed AI into internal processes and customer journeys. You will lead and develop a dedicated team with strong analytical foundations, maximizing automated resolution and driving global brand loyalty for millions of travelers through superior customer satisfaction.

Key Responsibilities

• 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.

Qualifications

• 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.

Nice to Have

• Background in travel-tech, global mobility, or hyper-growth e-commerce.

• Familiarity with predictive analytics for intent recognition, churn modeling, and automated data tracking.

• Experience mentoring and upskilling technical talent into stronger engineering practice.

Benefits & 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.