Head of Strategic Initiatives, CX & Ops

Holafly

Head of Strategic Initiatives leading CX and Operations transformation at Holafly, a global eSIM provider. Using SQL, financial modelling, AI, and cross-functional influence to deliver measurable impact.

Posted 8/17/2026full-timeRemote • 🇮🇪 IrelandLeadWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in Customer Experience and Operations leadership, with a strong focus on data-driven decision-making, advanced SQL proficiency, and the ability to deliver measurable impact in fast-paced environments. Proven track record in building analytical models, creating executive presentations, and orchestrating cross-functional collaboration.

Highest-signal resume keywords

Advanced SQL ProficiencyP&L AccountabilityExecutive Presentation SkillsAnalytical Model DevelopmentExperience in Management Consulting

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

SQLFinancial ModellingData AnalysisProcess RedesignAnalytical Model Building

Soft Skills

Written CommunicationStakeholder EngagementInfluenceProblem-SolvingAdaptability

Tools & Technologies

AI ToolsSpreadsheetsSteering Committees

Industry Keywords

Customer ExperienceDigital TransformationProduct-Led GrowthTravel-TechCX Metrics

Tech Stack

Tools & technologies

SQL

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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