Director, Product Management (Payments)

Accountabilities:: Define product strategy and business outcomes: Develop and communicate a multi-year Payments product vision and roadmap aligned with corporate objectives, OKRs, and profit-and-loss targets. Own commercial performance: Drive key business metrics, including Gross Payment Volume (GPV), payments penetration and share of checkout, new paid sales, merchant onboarding conversion, and payments revenue. Lead and develop product teams: Manage, coach, and empower Group Product Managers and Senior Product Managers across Retail and Hospitality platforms, establishing clear expectations and accountability. Build organizational capability: Recruit high-performing product talent, develop internal leaders, create career progression opportunities, and establish succession plans. Strengthen product management excellence: Raise standards across product discovery, commercial modeling, pricing and packaging, prioritization, and data-driven execution. Drive cross-functional alignment: Partner with Engineering Directors, Design leaders, Product Marketing, Sales, Operations, and Finance to align product strategy, commercial objectives, and delivery priorities. Manage strategic payment partnerships: Build and maintain relationships with payment processors and acquiring partners, contributing to decisions about which capabilities to build internally, purchase, or develop through partnerships. Consolidate and evolve the payments platform: Bring fragmented payment capabilities together into a coherent, scalable platform that delivers consistent experiences across product lines. Balance strategic and operational priorities: Manage long-term platform investments alongside quarterly commitments, making clear and timely trade-offs in complex or uncertain situations. Represent product strategy at executive level: Communicate product direction, performance, key metrics, and strategic recommendations to C-suite leaders and the Board. Establish effective product governance: Improve discovery and delivery practices, promote systems thinking, and support continuous improvement across multiple product teams. Requirements: Leadership experience: At least 2–3 years in a Director-level or equivalent product leadership position, managing larger teams through direct and indirect reports, including Group Product Managers. Business ownership: Demonstrated ownership of a complete line of business or major product vertical, such as payments, billing, or point-of-sale (POS), with clear accountability for commercial performance. Talent development: Proven ability to recruit, coach, develop, and promote product leaders while building strong, accountable teams. Organizational transformation: Experience leading significant structural, technical, or strategic change within a mature technology organization. Executive communication: Strong presence and credibility when working with Vice Presidents, C-suite executives, and other senior stakeholders. Commercial and financial expertise: Deep understanding of business models, unit economics, pricing strategies, and the impact of product decisions on profit and loss. Payments industry knowledge: Strong understanding of payment ecosystems, including acquiring, interchange, settlement, reconciliation, and compliance. Technical platform expertise: Solid knowledge of platform architecture, APIs, and microservices, with experience leading platform consolidation and migration initiatives. Data-driven decision-making: Familiarity with data infrastructure, conversion funnels, analytics, and reporting pipelines to guide product strategy and measure outcomes. Operational reliability: Experience overseeing business-critical, high-availability customer journeys and payment flows. Product delivery methodologies: Familiarity with lean product development, agile frameworks, and continuous delivery across multi-team organizations. Systems and portfolio thinking: Ability to understand how products and capabilities interact across a broader ecosystem rather than treating features as isolated initiatives. Leadership through others: Skilled at achieving results by coaching and empowering product leaders rather than focusing on individual squad-level execution. Strategic judgment: Able to navigate ambiguity, anticipate business needs, make high-impact decisions, and define long-term direction aligned with company strategy. Customer orientation: Strong merchant empathy and an understanding of the needs of both retail and hospitality businesses. Results-driven mindset: Demonstrated ability to deliver ambitious outcomes, overcome obstacles, and maintain accountability for execution. Candidates are encouraged to apply even if they do not meet every listed requirement, as relevant experience and transferable skills are valued. Benefits: Annual base salary: CA$220,000–CA$250,000 for candidates hired to work in Ontario, depending on qualifications, skills, experience, and market conditions. Performance-based bonus, with the role's compensation package indicating a bonus opportunity of approximately 70%–80%. Equity options. Flexible paid time off. Remote work flexibility. Medical, dental, and wellness benefits. Life and disability insurance. Retirement savings contributions through an RRSP plan with employer matching. Enhanced paid parental leave. Health and wellness credit. Professional development and continuous learning opportunities. Global mobility opportunities. Paid time off for volunteering and community involvement. Employee interest groups, employee-led networks, social committees, and sponsored sports teams. Computer purchase program, including the opportunity to purchase a personal MacBook. An inclusive and collaborative work environment with opportunities for career growth and meaningful impact.