Director, Product Management – Expansion, Retention & Payments

This is a fully remote position, open to applicants in Canada.

📋 Description

• Manage our global payments platform, focusing on enhancing checkout conversion rates, subscription renewals, and fraud/risk management strategies.

• Lead the Product-Led Growth (PLG) strategy aimed at self-service retention, account expansion, and effectively connecting high-value product users with our SME and Enterprise sales teams.

• Oversee, mentor, and expand a high-achieving team of Growth and Payments Product Managers to meet key revenue objectives across the company.

• Take ownership of the PLG Expansion Strategy by defining and implementing the roadmap for self-service upgrades, cross-sells, and seat expansion to optimize customer lifetime value (LTV) within the self-service segment.

• Create the Self-Serve-to-Enterprise connection by designing and refining Product-Qualified Lead (PQL) funnels.

• Propel Global Retention and manage the entire subscriber retention lifecycle.

• Direct the roadmap for a scalable, compliant, and adaptable global payments platform.

• Oversee experimentation frameworks, KPIs, and strategic analyses to guide executive decision-making regarding monetization structures and customer LTV.

⛳️ Requirements

• A minimum of 7 years of Product Management experience, with at least 3 years in a leadership or people management role.

• Extensive knowledge in Product-Led Growth (PLG), particularly in optimizing SaaS funnels, retention loops, and self-serve-to-enterprise (sales-assisted) pipelines.

• Expertise in Billing, Payments, and Monetization platforms (e.g., checkout optimization, global payment methods, compliance, and fraud prevention).

• Highly analytical with a proven history of managing revenue-focused metrics (GRR, NRR, Conversion) and executing rigorous A/B testing frameworks.

• Capability to navigate complex cross-functional settings while influencing stakeholders across Engineering, FP&A, Legal, and Sales.

• Outstanding communication skills, capable of translating complex architectural or financial concepts into clear strategic narratives for executive leadership.

🏝️ Benefits

• Medical, dental, vision, life, and disability insurance

• RRSP matching

• Flexible spending & health savings account

• Paid holidays

• Paid time off

• Employee assistance program

• Other company benefits