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Job Title


Head of Product – iGaming & Sports Betting


Company : Initiate International


Location : windsor, Ontario


Created : 2025-12-17


Job Type : Full Time


Job Description

Own the product vision for a high-growth iGaming and sports betting brand and decide what gets built, why, and in what order.Our client is a fast-scaling online betting and gaming operator with big plans across North America. They are looking for a Head of Product who can blend strategic thinking with ruthless prioritisation and hands-on leadership someone who can turn an ambitious roadmap into live, revenue-generating features at pace.If you live at the intersection of customer, data, and delivery and you want a real mandate to shape a product used every day by passionate players this is the role.As Head of Product, you will own the end-to-end product strategy and roadmap across sportsbook, casino, and player experience. You will lead a team of Product Managers and work closely with Engineering, Design, Data, CRM, and Trading to deliver a world-class platform that balances excitement, usability, and regulatory rigour.You will be responsible for setting direction, making trade-offs, killing weak ideas quickly, and doubling down on what moves the needle.What You Will Do:Define and own the product vision, strategy, and roadmap for sportsbook, casino, and player journeys across Canada and other key markets.Lead and develop a team of Product Managers, setting clear objectives, standards, and ways of working.Translate company objectives into concrete product goals, initiatives, and releases with clear success metrics.Work closely with Engineering and Design to deliver features that are feasible, scalable, and delightful to use.Prioritise ruthlessly: balance player impact, commercial value, regulatory requirements, and technical constraints.Champion a data-driven product culture using analytics, experimentation, and customer feedback to guide decisions.Own the backlog at a strategic level: ensure the right bets are being made, and that delivery squads are focused on the highest-impact work.Partner with Compliance, Risk, and Responsible Gambling teams to ensure products meet regulatory and licensing obligations in all jurisdictions.Collaborate with Marketing, CRM, and Operations to ensure seamless campaigns, promotions, and lifecycle journeys are supported in-product.Drive continuous optimisation of the core flows: registration, KYC, deposit, bet placement, gameplay, withdrawal, and reactivation.Monitor competitive landscape, market trends, and emerging features in iGaming and sports betting and use them to sharpen strategy.Report to senior leadership on product performance, trade-offs, and progress against roadmap with clear, actionable insight.What You Bring:Significant experience in product leadership roles (e.g. Head of Product, Product Lead, Senior Product Manager) within iGaming, sports betting, online casino, or a closely related high-scale B2C digital product.Proven track record owning a product roadmap and delivering impactful features from concept through to launch and iteration.Strong understanding of sportsbook and/or casino products, player behaviour, and what differentiates a great iGaming experience from a mediocre one.Deep familiarity with experimentation and analytics A/B testing, funnel analysis, cohorts, retention, LTV, etc.Experience working in cross-functional squads with Engineering, Design, Data, and Marketing.Comfortable making hard prioritisation calls with incomplete information and defending them with clear logic.Strong stakeholder management and communication skills able to align execs, engineers, and commercial teams around the same plan.Experience operating in regulated environments (e.g. Ontario and other regulated markets) and working closely with Compliance and Risk.Leadership skills: coaching and developing Product Managers, setting standards, and building a strong product culture.Relevant skills and exposure: Product strategy and roadmap ownership, sportsbook/casino UX, customer research, experimentation, KPI definition, funnel and cohort analysis, backlog management, agile methodologies, stakeholder management, product discovery and delivery.Whats In It For You?End-to-end ownership: You will set the vision and decide where the product goes next across multiple verticals and markets.Direct commercial impact: Product decisions are tightly linked to acquisition, retention, and revenue you will see the results of your work clearly.Build and scale: Shape how product is done team structure, rituals, toolset, and culture in a business that is still growing fast.Strategic seat at the table: Work closely with C-level leadership on growth, market expansion, and long-term product bets.Remote flexibility: Work from anywhere in Canada, with occasional travel for on-site workshops, planning sessions, and key events.Attractive package: Competitive salary, performance-based incentives, and benefits aligned with a senior leadership role.Interested?If you are a product leader who understands iGaming and sports betting, and you want the mandate to shape a platform at scale across Canada and beyond, we would like to hear from you.Please submit your CV along with a concise overview of a product or product area you led that drove meaningful growth including the problem, your approach, and the impact delivered.