Head of Strategic Initiatives, CX & Ops

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Logo of Holafly

Holafly

501 - 1000 employees

Founded 2017

✈️ Travel

📡 Telecommunications

👥 B2C

💰 $112.9k Seed Round - Holafly on 2019-06

Travel • Telecommunications • B2C

Holafly is a travel connectivity provider that sells eSIMs and prepaid international SIM cards to travelers, enabling mobile data access across multiple countries without relying on traditional roaming plans. It operates primarily through an online storefront and targets consumers such as tourists and digital nomads who need short-term, flexible mobile data while abroad.

📋 Description

• Lead Holafly’s highest-priority Customer Experience and Operations initiatives • Own end-to-end execution from scoping and stakeholder alignment through measurable delivery • Build data-backed frameworks, ROI models, and investment proposals • Use SQL and financial modelling to validate hypotheses, diagnose friction points, and track transformation success • Orchestrate delivery across Product, Tech, Marketing, and Operations through influence • Create executive presentations, board updates, strategic proposals, and post-mortems • Diagnose and redesign underperforming processes for global scale • Report directly to the Chief Customer Experience Officer • Translate CX and Operations leadership vision into execution and measurable impact

🎯 Requirements

• 5–7 years of experience • Experience in top-tier management consulting (MBB), internal strategy or transformation at a high-growth scale-up, or senior operations/chief of staff roles • Demonstrable P&L or delivery accountability • Advanced SQL proficiency • Ability to build analytical models from scratch • Exceptional executive presentation and written communication skills • Track record of delivering measurable impact from ambiguous briefs in fast-moving environments • Comfort with spreadsheets and steering committees • Ability to identify and apply generative, agentic, or analytical AI tools • Ability to build the case for AI adoption and engage non-technical stakeholders • Bonus: digital transformation, product-led growth, or travel-tech experience • Bonus: hands-on AI experience transforming contact centre operations • Bonus: fluency in Spanish • Bonus: exposure to CX metrics such as NPS, CSAT, CES, and churn

🏖️ Benefits

• Competitive salary, benchmarked to experience and the market • 100% remote work with full flexibility • High-trust ownership culture • Direct exposure to C-suite decision-making • Growth trajectory toward owning a line function or domain leadership position • Opportunity to work on problems shaping the experience of millions of travellers worldwide • Inclusive environment and equal opportunity employment

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