Director, Product Management - Expansion, Retention & Payments

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, Product Management - Expansion, Retention & Payments based in Canada.

This role offers the opportunity to lead high-impact product strategies that directly influence revenue growth, customer retention, and business expansion.
You will oversee critical product areas spanning payments, monetization, product-led growth, and customer lifecycle optimization.
The position combines strategic leadership, data-driven decision-making, and close collaboration with engineering, finance, sales, and growth teams.
You will shape the future of self-service experiences by improving conversion, reducing churn, and creating scalable pathways for enterprise growth.
As a product leader, you will manage and mentor talented teams while influencing company-wide priorities and executive decisions.
This is an opportunity to drive measurable business impact by building innovative solutions that improve customer value and long-term growth.

• Lead and scale product teams focused on growth, payments, monetization, and customer lifecycle initiatives, ensuring alignment with strategic business objectives.
• Define and execute the product-led growth strategy, including self-service upgrades, cross-sell opportunities, and account expansion initiatives to maximize customer lifetime value.
• Own the strategy and roadmap for global billing and payments platforms, enabling scalable monetization models, flexible pricing structures, and enterprise-ready billing capabilities.
• Drive improvements across checkout conversion, subscription renewals, payment experiences, and revenue optimization initiatives.
• Develop and optimize self-service-to-enterprise growth pathways by improving product-qualified lead funnels and creating seamless transitions for high-value customers.
• Lead retention strategies by designing product experiences, lifecycle interventions, and win-back programs that improve customer loyalty and reduce churn.
• Establish experimentation frameworks, analytics practices, and key performance indicators to guide monetization and growth decisions.
• Partner closely with Engineering, Finance, Sales, Growth, Tax, and Legal teams to deliver scalable and compliant product solutions.
• Communicate product strategy and business impact to executive stakeholders, influencing decisions through clear insights and strategic recommendations.

Requirements:

• 7+ years of Product Management experience, including at least 3+ years leading product teams or managing product leaders.
• Proven expertise in Product-Led Growth (PLG), SaaS business models, customer retention strategies, and self-service growth funnels.
• Strong experience with billing, payments, monetization platforms, checkout optimization, subscription models, and revenue-focused product strategies.
• Demonstrated ability to own and improve revenue-driving metrics such as conversion rates, gross retention, net retention, and customer lifetime value.
• Strong analytical mindset with experience using experimentation, A/B testing, and data insights to guide product decisions.
• Ability to navigate complex cross-functional environments and influence teams across engineering, finance, legal, sales, and business operations.
• Exceptional leadership and communication skills with the ability to translate technical and financial concepts into clear strategic narratives.
• Experience building scalable product strategies in fast-moving technology environments.
• Strong customer-focused mindset with the ability to identify opportunities that improve user value and business outcomes.

Benefits:

• Competitive annual compensation range of CAD $178,500 - $210,000 depending on location, experience, skills, and qualifications.
• Additional bonus and compensation opportunities as part of the total rewards package.
• Fully remote work environment with flexibility to support different working styles.
• Comprehensive health benefits, including medical, dental, vision, life, and disability insurance.
• Retirement savings plan and financial wellness benefits.
• Flexible spending and health savings account options.
• Paid holidays and paid time off to support work-life balance.
• Employee assistance programs and wellness resources.
• Opportunities for professional growth and leadership development.
• Inclusive culture focused on collaboration, innovation, and meaningful impact.