Head of Finance - Calico AI

Location: Toronto (Hybrid)
Reports to: Chief Executive Officer (Canada HQ)
Experience Level: 5–8 years

Calico AI is transforming how consumer brands bring products to life — we are the agentic AI copilot for sourcing, production, and global supply-chain orchestration.

Calico serves as the intelligence layer for global manufacturing, automating design-to-delivery decisions for leading apparel and accessories brands.

We’re building a global business with strong foundations: operational rigor, real-time financial visibility, and trusted relationships with customers, suppliers, and investors. This is a role for a hands-on architect who can automate financial workflows, integrate data pipelines, and build a finance function that runs as efficiently as our technology.

Calico AI is seeking a Head of Finance (Canada HQ / U.S. Revenue Operations) to lead financial operations, reporting, and planning across our global structure.

This is a hands-on systems-builder role — ideal for someone who enjoys architecting processes, implementing automation, and connecting financial data across borders. You’ll oversee all aspects of finance for Calico’s Canadian HQ while ensuring the company’s U.S. revenue operations run with clarity, compliance, and efficiency.

You’ll partner directly with the CEO and cross-functional teams spanning Operations, Commercial, and Technology to deliver clean financial data, actionable insights, and scalable infrastructure.

• Lead the company’s FP&A function, including quarterly and annual budgeting, forecasting, and performance tracking.

• Build financial models and earnings projections that inform strategic decision-making for both Canadian HQ and U.S. commercial teams.

• Partner with leadership to align operational goals with financial objectives, ensuring spending discipline and ROI visibility.
  

• Collaborate with Commercial and Brand Management teams to translate U.S. customer forecasts into accurate revenue projections.

• Drive analysis of revenue performance, cost-to-serve, and customer-level profitability.

• Support Business Development by modeling new customer scenarios, pricing strategies, and lifetime value assessments.
  

• Oversee all accounting, tax, and treasury operations for Calico’s Canadian HQ, ensuring compliance with Canadian and U.S. regulations.

• Manage cash flow forecasting, banking relationships, and working capital requirements across entities.

• Ensure accurate, timely payroll and expense processing for multi-currency, cross-border operations.

• Coordinate intercompany transactions and revenue repatriation from U.S. operations to Canada, optimizing for compliance, efficiency, and tax effectiveness.
  

• Design and implement a modern finance stack that automates data flow between systems like QuickBooks, Ramp, Carta, and Monday.com.

• Integrate financial reporting with operational and CRM data to create real-time visibility across departments.

• Develop repeatable, automated workflows for closing, variance analysis, and management reporting.

• Continuously identify new tools and integrations that improve accuracy and reduce manual workload.
  

• Serve as the financial anchor for Calico’s Canadian HQ, ensuring all reporting, controls, and systems align with global policies.

• Partner with technology, operations, and customer teams to drive data consistency and improve reporting accuracy.

• Support investor relations, board reporting, and due-diligence preparation for future fundraising rounds.

• Provide actionable insights that connect financial performance with business strategy.
  

• 5–8 years of progressive experience in finance, accounting, or FP&A roles, ideally within high-growth, multi-entity organizations.

• Experience with U.S.-based revenue operations and familiarity with cross-border financial structures.

• Proven ability to implement automation and system integrations across finance, CRM, and operations tools.

• Strong understanding of GAAP/IFRS, tax, and treasury management in both Canadian and U.S. contexts.

• Advanced analytical and financial modeling skills, with the ability to translate data into clear insights.

• Highly organized, self-sufficient, and motivated by building lean, scalable systems rather than managing large teams.

• CPA, CFA, or relevant accounting designation preferred but not required.