Lead, Finance Analytics & Enablement AI/ML

Hopper Inc.

Job Overview

Location

Toronto - Remote

Job Type

Full-time

Full Job Description

📋 Description

• Lead, Finance Analytics & Enablement AI/ML at Hopper Inc. to own data warehouse, business intelligence, GCP/AI optimization, and Finance AI enablement strategy, reporting directly to the CFO and serving as a key business partner across the organization.
• Provide actionable insights to drive business decisions, own data warehouse strategy and governance, build and lead a Center of Excellence for reporting, and create and implement the Finance AI automation roadmap in partnership with FP&A, accounting, and data teams.
• Establish data pipeline and AI model foundation, optimize GCP infrastructure costs with engineering and Financial Operations, establish Finance as the single source of truth for financial and business performance, and manage a team of 4 engineers and 1 finance and strategy manager.
• Drive internal controls, support external audits related to data governance, and enable self-service analytics for key stakeholders while fostering a culture of first-principles thinking and clear communication with senior leadership and external partners.

🎯 Requirements

• 15+ years of work experience in travel and/or SaaS
• Bachelor's Degree with strong preference for Master's degree or equivalent experience
• Engineering background preferred
• Fluency in SQL, Python, GCP and Data Science with 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)
• Strong data reconciliation skills across large, multi-source datasets
• Bias toward first-principles thinking — questioning assumptions, stress-testing processes, and asking why
• Clear communicator with senior leadership and external partners
• Comfort with ambiguity and ground-zero building

🏖️ Benefits

• 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
• 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

Skills & Technologies

Python

GCP

Datadog

Senior

Remote

Degree Required

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Hopper Inc.

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About Hopper Inc.

Hopper is a travel technology company that uses predictive analytics and machine learning to forecast flight and hotel prices, allowing consumers to book travel at optimal times. Founded in 2007 and headquartered in Montréal, Canada, it operates mobile-first booking platforms and provides fintech products like price freeze, cancel-for-any-reason, and rebooking guarantees to reduce travel risk.

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