Job Overview

BET99 is Canada's Premiere Online Sportsbook and Casino. Launched in 2020, we have consistently innovated the online gaming landscape every step of the way, exponentially growing our customer base and, in turn, our internal BET99 team! We’re a fast-paced company and are looking for individuals who live and breathe our core values: challenging the status quo, trust, transparency, integrity, and collaboration.

The Senior Technical Project Manager plays a pivotal role in driving structured, predictable, and high-quality technical delivery across cross-functional teams. This position is responsible for planning, prioritizing, and coordinating technical initiatives while ensuring alignment between Product, Engineering, Compliance, and external partners.

With a strong focus on execution discipline, dependency management, and delivery governance, you will ensure that technical deliverables are sequenced effectively, risks are proactively mitigated, and teams remain aligned throughout the development lifecycle. You will work closely with Stakeholders, Technical Analyst and QA during refinement and planning sessions to ensure initiatives are clearly defined, properly estimated, and realistically scheduled.

You will be part of a collaborative, high-performing team that values accountability, transparency, and operational excellence.

Vacancy Status: New

Day In the Life

You will lead sprint planning and roadmap alignment sessions to ensure deliverables are properly prioritized and sequenced Collaborate daily with Stakeholders, Engineering, and Technical Analysts to align scope, timelines, and resource allocation Own release planning and ensure dependencies across multiple squads are identified and managed Facilitate refinement sessions and support backlog readiness prior to development commitment Track delivery progress, velocity, and milestone adherence across concurrent initiatives Proactively identify risks, bottlenecks, and cross-team blockers, driving resolution in a timely manner Coordinate technical releases, ensuring readiness across Engineering, QA, DevOps, and Compliance Align 3rd party integrations with internal delivery schedules and manage timeline expectations Ensure Jira boards and reporting tools accurately reflect project status and priorities Support post-release reviews and continuous improvement initiatives to optimize delivery performance

Responsibilities

Own end-to-end planning and coordination of technical initiatives across multiple teams Develop and maintain delivery roadmaps, sprint plans, and release schedules Prioritize technical deliverables in alignment with business objectives and regulatory timelines Facilitate sprint ceremonies including planning, backlog grooming, stand-ups (as needed), and retrospectives Partner closely with Technical Analysts during refinement to ensure scope clarity and readiness Manage cross-team dependencies and ensure proper sequencing of technical workstreams Monitor project health using defined KPIs (velocity, burn-down, capacity, milestone tracking) Identify delivery risks, constraints, and resource conflicts, implementing mitigation strategies proactively Coordinate internal stakeholders and external vendors to ensure timely completion of integration and platform initiatives Ensure development teams are not overcommitted and capacity planning aligns with realistic throughput Drive accountability across teams while fostering a collaborative and solution-oriented environment Provide regular status reporting to leadership with clear visibility into progress, risks, and upcoming milestones Contribute to process optimization, delivery governance improvements, and Agile maturity initiatives

Skills and Qualifications

Minimum 10 years of experience in Technical Project Management, Delivery Management, or similar role within a software development environment Strong experience managing cross-functional technical teams in Agile environments Demonstrated ability to manage multiple concurrent initiatives with competing priorities Proven track record of delivering API integrations and complex system-based projects Strong understanding of software development lifecycle (SDLC), release management, and dependency planning Experience facilitating Agile ceremonies and managing sprint planning activities Strong organizational and prioritization skills with high attention to detail Excellent stakeholder management skills across Product, Engineering, Compliance, and third-party vendors Strong analytical mindset with the ability to identify risks early and drive structured mitigation Excellent verbal and written communication skills Experience using Jira or equivalent project management tools Comfortable operating in fast-paced, high-growth environments

Nice to Have

Agile (PMI-ACP, CSM) or Project Management (PMP) certification Background in software engineering, systems architecture, or technical analysis Experience within online gaming, fintech, or other regulated digital industries Familiarity with compliance-driven delivery across multiple jurisdictions Experience managing payment integrations or transactional systems Strong understanding of DevOps workflows and release pipelines Experience scaling delivery processes in growing technology organization

Why Join BET99? Come for the career… stay for the culture. Canada-wide remote freedom - your office is anywhere you want it to be. Time off that feels good - paid vacation, paid sick days, plus your birthday off on us. Early access to leadership - meet the CEO in your first 30 days and see how your work truly makes an impact. Open-door leadership style - transparency and collaboration are core to how we operate. Premium benefits - 100% employer paid, for you and your family. Built-in career acceleration - Mentorship Programs led by industry veterans. A community you’ll want to be part of - book clubs, monthly employee events, cross-team fun, and more. Bring a friend, earn a bonus - our referral program rewards great connections. Regular recognition programs - so your great work never goes unnoticed. Modern tools and tech - making your job smoother, not harder. A streamlined onboarding process - hit the ground running with confidence. A company that invests in long-term relationships, not quick wins.

Disclaimers

This position does not use artificial intelligence during the hiring process.