About Holafly
Holafly is a high-growth scale-up revolutionizing how businesses and travelers connect to the internet abroad. Since 2018, we've empowered travelers in over 200 destinations worldwide with secure and reliable eSIM solutions. With a team of 500+ professionals across multiple countries, we scale globally to support seamless, unlimited data connectivity.
Role Overview
As Head of CX Automation & AI, you will own and scale Holafly's comprehensive AI and automation strategy across the entire CX landscape. You'll refine current infrastructures, uncover high-impact opportunities to embed AI into internal processes and customer journeys, and lead a dedicated team to maximize automated resolution and drive global brand loyalty for millions of travelers.
Key Responsibilities
- Own and scale AI and automation strategy across customer-facing and agent-facing experiences, identifying high-impact opportunities to embed conversational AI into key user journeys.
- Lead team roadmap and project planning, prioritizing initiatives and resourcing in collaboration with Product and Project Managers.
- Lead and grow an elite AI & Automation team, building on strengths and raising the technical bar in engineering practices and AI implementation.
- Architect and refine CX automation infrastructure, from chatbots and CX platforms to agent-facing tools, ensuring frictionless handovers between bots and human agents.
- Track and act on essential CX metrics including CCR, deflection rate, FCR, CSAT, and intent recognition accuracy to eliminate journey friction.
- Report on cost-per-contact and containment-driven savings to leadership, alongside quality trade-offs.
- Establish robust AI governance frameworks aligned with data privacy, responsible AI practices, and regulatory baselines like the EU AI Act.
- Own incident management across the CX automation stack, ensuring fast triage and resolution of technical and customer-impacting issues.
- Manage relationships with CX platform and AI technology providers, overseeing vendor performance, contracts, and product roadmap influence.
- Act as hands-on AI advisor on cross-functional initiatives, ensuring AI strategy consistency across the CX ecosystem.
Required Qualifications
- Proven track record defining, deploying, and scaling sophisticated LLM, chatbot, and AI-driven automation projects in live production environments.
- Demonstrated experience leading and upskilling technical teams with coaching and capability-building expertise.
- Deep technical mastery of NLP, prompt engineering, complex data workflows, and conversational architecture.
- 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 SLA accountability.
Nice to Have
- Background in travel-tech, global mobility, or hyper-growth e-commerce.
- Familiarity with predictive analytics for intent recognition and churn modeling.
- Experience mentoring technical talent in stronger engineering practices.
Benefits & Perks
- 100% remote flexibility, open to candidates in EMEA, Northern Europe, or Africa.
- Flexible working hours supporting work-life balance and well-being.
- Real ownership and autonomy to shape the technical future of a global market leader.
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