Location: Toronto, ON (Hybrid)

Position: Full-Time, Permanent

Seniority Level: Senior level

About the Role

Webware.ai is looking for a high-performance strategic Finance Director to lead

and execute all financial operations and elevate the company’s financial strategy

as we scale the business. The role is a combination of tactical execution and

strategic planning in a highly entrepreneurial environment.

This is a critical leadership role, reporting directly to the CEO/Integrator.

The ideal candidate is both a builder and an operator: someone who is strong at

project management but also can roll up their sleeves and go deep. The ideal

candidate also possesses strong financial acumen but can also work across

departments and support sales, marketing and operations.

Key Responsibilities

Strategic Reporting, Financial Planning & Profitability Analysis

• Lead stakeholder reporting, including investors, partners, banking relationship etc.
• Lead annual budgeting processes at both strategic and operational levels.
• Own forecasting and modelling.
• Develop reporting frameworks that highlight channel CAC, LTV, cohort margins,

and contribution margins

• Partner cross-functionally with Marketing, Product, and Operations teams to enhance unit economics and drive sustainable, profitable growth.
• Support board-level meetings, including planning and presentation.

Accounting and Financial Management

• Oversee the preparation and accuracy of financial statements, including income statements, balance sheets, and cash flow reports.
• Oversee and optimize Accounts Payable (AP) and Accounts Receivable (AR) processes.
• Perform monthly variance analysis against the budget and forecasts.
• Lead year-end review.
• Oversee payroll administration and tax compliance

Cash Flow and Treasury Management

• Design and maintain short, mid, and long-term cash flow forecasts.
• Manage cash strategically to optimize working capital and fund operational and strategic initiatives.

Lead other items as assigned

✅ You’ll Crush This Role If You…

• 10+ years of progressive experience in financial leadership roles in startup, scale-up, or D2C environments.
• CPA or equivalent financial credential preferred.
• Experience with QuickBooks, Stripe, financial modelling, etc.
• Love taking ownership and moving fast without waiting for permission
• Demonstrated success in a high-growth, tech, or startup environment, preferably

with experience in digital marketing.

✨ Perks & Culture

• EOS-driven company with strong systems and clear Rocks
• Collaborative, positive, and high-performance team
• Opportunity to shape finance and operations in a rapidly growing AI company