Head of Data & Analytics

HUB International•St. Petersburg, FL

1d•$120,000 - $170,000•Remote

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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