Senior Product Manager

Webcomconnect; Newmarket; On-site; CAD 120,000 - 160,000; Full time

Job summary

Webcomconnect is seeking a Senior Product Manager to lead the roadmap and drive complex product initiatives across a regulated digital platform.

You will collaborate with engineering, design, legal, compliance, operations, and leadership to improve player engagement, onboarding, and monetization while balancing strategic thinking with hands-on execution.

Qualifications

• 5+ years of product management with senior-level responsibilities.
• Proven ability to own and deliver complex product initiatives independently.
• Experience collaborating with engineering in agile environments.
• Excellent organizational and project management skills.

Responsibilities

• Own the roadmap and day-to-day product direction for key platform areas.
• Translate business needs into PRDs, user stories, and acceptance criteria.
• Collaborate with engineering, design, and compliance to deliver features.
• Ensure timely releases and align with user and business expectations.
• Lead cross-functional product reviews and stakeholder discussions.

Skills

Product ownership

Stakeholder management

Agile methodologies

Cross-functional collaboration

Strategic thinking

Decision making

Tools

Jira

monday.com

Linear

Job description

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 fast-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.