About the Role
Hopper is looking for a Lead, Finance Analytics & Enablement AI/ML to own our data warehouse, business intelligence, GCP/AI optimization, and Finance AI enablement strategy. You will be a key business partner across the organization, managing partner relationships across a broad range of commercial arrangements, reporting directly to the Chief Financial Officer.

What would your day-to-day look like

Provide actionable insights to drive business decisions based on finance and data analytics

Own the data warehouse strategy, governance and execution of the finance ledger

Build and lead a Center of Excellence for reporting including owning infrastructure and metrics across finance and the business units

Create, own, implement and track success of the Finance AI automation roadmap in partnership with FP&A;, accounting and data

Establish data pipeline and AI model foundation

Understand and optimize our GCP infrastructure costs in partnership with engineering and Financial Operations

Establish Finance as the single source of truth for financial and business performance and create self‑service analytics for key stakeholders

Manage a team of 4 engineers and 1 finance and strategy manager

Establish internal controls and support external audits related to data governance

An ideal candidate has

Work experience 15+ years in travel and/or SaaS

Bachelor's Degree, with a solid preference for a Master's degree or equivalent experience

Engineering background preferred

Fluency in SQL, Python, GCP and Data Science, hands on coding ability

Understanding of LLM‑based systems, prompt design,



and AI model evaluation frameworks

Familiarity with automation frameworks and observability tools (Amplitude, Datadog, Looker) to assess reliability and performance

Strong data reconciliation skills across large, multi‑source datasets

A bias toward first‑principles thinking — questioning assumptions, stress‑testing processes, and always asking why something works the way it does

Clear communicator with senior leadership and external partners

Comfort with ambiguity and ground‑zero building

Nice to Have

Background at a high‑growth technology or marketplace company

Experience working cross‑functionally with data engineering or warehouse teams

Perks and benefits of working with us

Well‑funded and proven startup with large ambitions, competitive salary and upsides of pre‑IPO equity packages.

Hopper covers 100% of the premiums for group insurance plan.

Hopper offers life, short term and long term disability coverage.

HSA that covers eligible medical and dental expenses.

All employees and dependents have access to Dialogue’s telemedicine services, anytime, anywhere.

All employees have access to an RRSP plan with automatic pre‑tax withdrawals per pay.

Please ask us about our very generous parental leave, much above industry standards!

Unlimited PTO.

Carrot Cash travel stipend.

Access to co‑working space on demand through FlexDesk AND Work‑from‑home stipend.

Entrepreneurial culture where pushing limits and taking risks is everyday business.

Open communication with management and company leadership.

Small, dynamic teams = massive impact.

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📌 Lead, Finance Analytics & Enablement AI/ML (Ontario)
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📍 Ontario