Director, Product Management - Expansion, Retention & Payments

Accountabilities:

• 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.

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