SENIOR PRODUCT MANAGER

We’re hiring a Senior Product Manager to join a growing digital platform business operating in a highly regulated consumer space. This role is ideal for someone who is confident leading complex initiatives independently and knows how to bring structure, clarity, and momentum to quick-moving product environments.

You’ll take ownership of key areas across our platform, working closely with engineering, design, legal, compliance, operations, and leadership teams to deliver features and experiences that improve player engagement, retention, onboarding, and monetization.

We’re looking for someone who is proactive, detail-oriented, and comfortable making decisions in environments where not everything is fully defined. You should be able to balance strategic thinking with hands‑on execution and know how to move projects forward without constant direction.

Key Responsibilities

Product Ownership & Strategy

Own the roadmap and day-to-day product direction for key platform areas

Take initiatives from discovery and planning through launch and post-release iteration

Translate business needs into clear product documentation including PRDs, user stories, workflows, and acceptance criteria

Identify opportunities to improve player experiences across onboarding, payments, promotions, gamification, loyalty, and retention

Use product insights, stakeholder feedback, and performance data to prioritize features and improvements

Delivery & Execution

Work closely with engineering and QA teams to manage sprint planning, backlog grooming, and release coordination

Keep projects moving by managing timelines, dependencies, risks, and shifting priorities

Provide clear requirements and resolve ambiguity quickly to support efficient development





Make thoughtful product decisions even when information is incomplete or evolving

Ensure releases are delivered on time and meet both user and business expectations

Cross-Functional Collaboration

Partner with legal, compliance, operations, brand, and leadership teams throughout the product lifecycle

Communicate project updates, trade-offs, risks, and timelines clearly to stakeholders

Manage competing priorities while maintaining focus on delivery and product quality

Lead product reviews, demos, and stakeholder discussions in a clear and structured way

Build alignment across teams while confidently pushing back when necessary

UX & Product Quality

Review user flows and designs with a strong attention to usability and player experience

Collaborate with design teams on wireframes and prototypes before development begins

Catch inconsistencies, edge cases, and friction points early in the process

Advocate for intuitive and high-quality user experiences across all touchpoints

Maintain a high standard for product quality and usability

Compliance & Regulatory Considerations

Work closely with legal and compliance teams to ensure product features meet regulatory requirements from the start

Support initiatives involving responsible gaming, sweepstakes mechanics, payments, and jurisdiction‑specific requirements

Navigate compliance considerations across regulated markets, including the US and Ontario

Balance innovation with operational and legal requirements in a fast‑changing environment





Required Experience

5+ years of product management experience, including experience operating at a senior level

Proven ability to independently own and deliver complex product initiatives

Strong experience working closely with engineering teams in agile environments

Excellent organizational and project management skills

Ability to manage multiple stakeholders and priorities across different teams

Strong written communication skills with experience creating structured product documentation

High attention to detail, especially around UX, workflows, and edge cases

Comfortable working in a scale‑up or fast‑paced environment where priorities can shift quickly

Preferred Background

Experience in iGaming, sweepstakes gaming, fintech, or another regulated digital product environment

Familiarity with gamification systems, loyalty programs, bonus mechanics, payment flows, or retention features

Understanding of sweepstakes compliance frameworks and/or Ontario iGaming regulations

Experience using tools such as Jira, monday.com, or Linear

Comfortable reviewing Figma files and collaborating closely with design teams

Exposure to KYC, identity verification, responsible gaming, or multi‑currency systems

Nice to Have

Experience working with PAM (Player Account Management) platforms

Familiarity with CRM and lifecycle marketing tools such as Smartico or Optimove

Experience supporting multi‑brand or white‑label products

This is an opportunity to play a key role in shaping products within a fast-growing and evolving digital industry. If you enjoy solving complex product challenges, working cross‑functionally, and building experiences that genuinely improve the customer journey, we’d love to hear from you.

📌 Senior Product Manager (East Gwillimbury)
🏢 Webcomconnect
📍 East Gwillimbury