Head of Data & Analytics
About The Position
At Squaremouth, our mission is simple: make travel insurance easy. We take complicated insurance products and turn them into a clear, simple comparison experience so travelers can find the coverage that gives them peace of mind. Our engineers play a huge role in making that possible. We’re looking for a Data & Analytics Lead to join our small, fast-moving team and help us level up how we measure and understand the business. You’ll own our core metrics and reporting, partner closely with Execs to answer high-impact questions quickly, and start shaping the roadmap for a modern data stack (warehouse, ETL/ELT, semantic layer) as we scale. This is a fully remote role. We’re based on US Eastern Time, and we welcome candidates who can collaborate during those hours.
Requirements
- 5+ years in analytics/BI/product analytics/analytics engineering (exact mix flexible).
- Proven experience building a metrics foundation and resolving “numbers don’t match” situations.
- Strong SQL + strong analytical judgment (you can be dropped into messy schemas and make order).
- Experience planning and/or implementing core data foundations (warehouse + ETL/ELT + modeling/semantic concepts).
- Early/first data hire experience; comfortable with ambiguity and ownership.
- Comfortable working independently in a distributed team.
Nice To Haves
- Experience with Introducing a transformation layer / semantic layer / modern warehouse approach.
- Marketplace/e-commerce funnels + attribution familiarity.
- Supporting experimentation programs.
- Defining the next data hires (roles, sequence, scope).
Responsibilities
- Build and own our data source of truth (canonical KPIs, definitions, reconciliation).
- Deliver fast, reliable insights for Exec, with a clear reporting cadence.
- Run the analytics operating system (intake, prioritization, stakeholder alignment).
- Raise dashboard trust (QA, validation, clear ownership).
- Enable measurement & experimentation (readouts, guardrails) as needed.
- Define the data platform roadmap (ETL/ELT, warehouse, semantic layer) and drive the first steps.
- Player/coach: ship work and mentor others to help them grow.
Benefits
- Salary: $120,000–$170,000 + bonus, depending on experience
- 401(k) match
- You’ll have a voice: we involve engineers in major decisions
- Remote-first: work from wherever you do your best work
- Small team, big impact: your work directly shapes a product used by millions of travelers
- Generous PTO: flexibility to take the time you need to rest and recharge
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
High school or GED
