Head of Strategic Initiatives (CX & Ops) - H027

About Holafly

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, reliable eSIM solutions. With a team of 600+ professionals across multiple countries, we are scaling globally to ensure our users stay connected from the second they land - wherever their journey takes them.

We're not just selling eSIMs. We're building the infrastructure of trust and experience that turns first-time buyers into lifelong travellers.

The Role

Reporting directly to the Chief Customer Experience Officer (CCXO), you'll be their strategic right hand - translating vision into execution and driving the highest-priority challenges across CX and Operations to measurable impact.

This isn't a coordination role. You'll own problems end-to-end: diagnosing them with data, building the case for change, orchestrating cross-functional teams to deliver, and communicating progress to leadership with clarity and conviction.

Think of it as the best parts of management consulting - sharp thinking, high-stakes problems, real variety - with the added dimension of genuine ownership and long-term impact. This role starts as an individual contributor and is built to grow: as you prove impact, there's a clear path to owning a broader mandate, potentially including people leadership, as Holafly scales.

What You'll Do

Drive Strategic Initiatives Own end-to-end execution of the CCXO's highest-priority projects - from initial scoping and stakeholder alignment through to measurable delivery. You step in where leadership presence is required but bandwidth is limited.

Build the Business Case Architect data-backed frameworks, ROI models, and investment proposals that justify and prioritise operational and commercial decisions. Your work gives leadership the confidence to move fast.

Work Independently with Data Use SQL and financial modelling to validate hypotheses, diagnose friction points, and track the success of transformation initiatives - without waiting for someone else to run the numbers.

Orchestrate Cross-Functional Delivery Manage by influence across Product, Tech, Marketing, and Ops. You know how to get teams aligned and moving without formal authority.

Communicate with Impact Turn complex, ambiguous problems into crisp executive narratives. Whether it's a board update, a strategic proposal, or a post-mortem, your decks and written communications set the standard.

Fix What's Broken Deep-dive into underperforming processes and redesign them for global scale. You're comfortable getting into the operational weeds when the situation calls for it.

What We're Looking For

• 5-7 years of experience, with a strong foundation in one or more of: top-tier management consulting (MBB), an internal strategy or transformation function at a high-growth scale-up, or a senior operations/chief of staff role with demonstrable P&L or delivery accountability

• Analytical rigour: advanced SQL proficiency and comfort building analytical models from scratch. You don't wait for a report - you build it, and draw the insight yourself

• Storytelling & communication: exceptional ability to craft compelling executive presentations and written narratives. You can take a messy, multi-stakeholder problem and distil it into a clear recommendation a board can act on

• Execution track record: a demonstrable history of taking projects from ambiguous brief to measurable impact in fast-moving environments. You're as comfortable in a spreadsheet as you are in a steering committee

• AI fluency & advocacy: you don't just follow AI trends - you know how to apply them. You're comfortable identifying where AI tools (generative, agentic, or analytical) can replace manual effort, improve customer outcomes, or unlock operational leverage. Critically, you can build the case for AI adoption and bring non-technical stakeholders along with you

Bonus Points

• Experience in digital transformation, product-led growth, or travel-tech environments

• Hands-on experience leveraging AI to transform contact centre operations

• Fluency in Spanish

• Exposure to customer experience operations or CX metrics (NPS, CSAT, CES, churn)

Compensation & Benefits

• Salary: Competitive, benchmarked to your experience and the market

• Remote-First: 100% remote with full flexibility and a high-trust ownership culture

• Leadership Access: Direct exposure to C-suite decision-making on the most critical challenges in the business

• Growth Trajectory: As Holafly scales, this role is built to grow with you, with a natural path toward owning a line function or domain leadership position

• Impact: You will work on problems that directly shape the experience of millions of travellers worldwide

Holafly is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive environment for all employees.