Head of Data & Analytics

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.

• 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.

• 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.

• 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).

• 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

We’re a tight-knit team that’s been simplifying travel insurance since 2003. We built Squaremouth to be a great place to work and the easiest way for travelers to find coverage that fits. In 2014, we launched Tin Leg, our own travel insurance brand focused on real traveler needs. It quickly became one of the most popular options on squaremouth.com.

Today, we’re more than 50 people who still move fast and care deeply about customers and teammates. We’ve been recognized as one of the Best Workplaces in America by Inc. Magazine and take pride in building both a great product and a great culture.

In 2023, we joined Specialty Program Group (SPG), giving us the resources to grow while keeping our startup spirit. So far, we’ve helped over 4 million travelers find coverage that gives them peace of mind, and we’re just getting started.

Salary Transparency:

Disclosure required under applicable state or municipality regulations: The expected draw range for this position will be $120,000 - $170,000 with additional bonus opportunity. This compensation will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as their historical book of business. A variable compensation package will be offered to enable the position to have high income earning capability. SPG is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.

#SPG

HUB International Limited is an equal opportunity employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations.

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