Initiate International

Senior Technical Project Manager

  • Initiate International

Job Description

Senior Technical Project Manager 

We are representing a high-growth, Canada-based online sportsbook and casino seeking an experienced Senior Technical Project Manager to lead complex software delivery initiatives in a regulated digital environment.

This is a fully remote opportunity across Canada, ideal for a senior-level Technical Project Manager with strong Agile delivery experience, API integration expertise, and a background in managing cross-functional software development teams.

If you thrive in fast-paced technology organizations and enjoy bringing structure, predictability, and governance to technical delivery, this role offers strong long-term career progression.

What You Will Do

As Senior Technical Project Manager, you will drive end-to-end software project delivery across multiple engineering squads.

Key responsibilities include:

  • Lead Agile sprint planning, roadmap alignment, and release management

  • Own technical project planning, scheduling, and dependency management

  • Coordinate cross-functional teams across Product, Engineering, QA, DevOps, and Compliance

  • Manage third-party and API integrations within defined timelines

  • Track delivery KPIs including velocity, burn-down, capacity, and milestone reporting

  • Identify and mitigate technical delivery risks and bottlenecks

  • Ensure backlog readiness and realistic capacity planning

  • Provide structured status reporting to senior stakeholders

This role requires strong governance, structured execution, and experience delivering complex system-based projects within regulated industries.

All About You

We are looking for a senior-level Technical Project Manager / Delivery Manager with:

  • 10+ years experience in technical project management within software development environments

  • Proven Agile delivery leadership across cross-functional engineering teams

  • Demonstrated success delivering API integrations, platform enhancements, and complex technical initiatives

  • Strong knowledge of SDLC, release management, and dependency planning

  • Experience using Jira or similar project management tools

  • Excellent stakeholder management and communication skills

  • Ability to manage multiple concurrent software projects with competing priorities

Highly desirable:

  • PMP, CSM, or PMI-ACP certification

  • Experience within online gaming, fintech, payments, or other regulated digital industries

  • Experience managing payment systems, transactional platforms, or DevOps-driven release pipelines

Additional Information

  • Fully remote opportunity (Canada-wide)

  • Competitive salary and comprehensive employer-paid benefits

  • High-growth technology environment

  • Strong leadership visibility and career progression opportunities

  • Structured onboarding and collaborative team culture

  • Salary: $115-140k per annum

If you are a results-driven Senior Technical Project Manager looking for your next remote leadership opportunity in a fast-scaling digital business, get in touch.

Disclaimers:

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