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.

📌 Lead, Finance Analytics & Enablement AI/ML (Toronto)
🏢 Hopper
📍 Toronto