Lead, Finance Analytics & Enablement AI/ML

About The Role

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 strong 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

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 with massive impact.

Compensation Range: CA$400K – CA$500K