Technical Project Manager

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the comprehensive planning and execution of strategic technology initiatives, including platform consolidation, Secure Retail-to-Solutions migration, database modernization, unified reporting, reliability enhancements, integrations, and AI-driven projects.

• Convert business objectives and product roadmaps into project charters, workstreams, milestones, dependencies, resource allocations, delivery forecasts, and acceptance criteria.

• Create and sustain integrated project plans involving Engineering, Product, Architecture, Data, Quality, Infrastructure, Customer Success, Support, Sales, and external partners.

• Lead kickoffs, planning meetings, weekly execution evaluations, risk and dependency assessments, decision forums, retrospectives, and executive status reports.

• Monitor scope, timelines, capacity, budgets, risks, assumptions, issues, decisions, and changes; facilitate resolutions and escalate with context and recommendations.

• Generate reports on planned versus delivered work, milestone health, delivery confidence, resource limitations, quality, readiness for release, and business outcomes.

• Organize release and migration readiness, including validation, cutover, rollback, communications, training, support preparedness, and post-launch stabilization.

• Collaborate with Product Managers and Engineering leaders regarding priorities, backlogs, commitments, customer requirements, architecture specifications, and delivery capacity.

• Enhance the technology delivery operating model, incorporating project intake, prioritization, status reporting, dependency management, RAID logs, decision records, and lessons learned.

• Manage and refine project-management workflows within Asana, Jira, or comparable platforms.

• Oversee vendor and contractor deliverables, including statements of work, milestones, invoices, risks, performance, and return on investment.

• Build trustworthy relationships, navigate ambiguity, and clarify decisions, ownership, next steps, and delivery tradeoffs.

⛳️ Requirements

• Bachelor's degree in Computer Science, Engineering, Information Systems, Business, Project Management, or a related field, or equivalent practical experience.

• Over 7 years of experience managing technology projects or programs, including complex initiatives that involve multiple engineering and business teams.

• Proven success in delivering SaaS software, platforms, data, cloud, integration, infrastructure, or migration projects throughout the entire lifecycle.

• Strong understanding of Agile and hybrid delivery methodologies, software development lifecycles, release management, and production-readiness practices.

• Experience in creating integrated project plans and managing scope, schedules, dependencies, resources, risks, budgets, vendors, and organizational change.

• Proficient in Asana, Jira, Azure DevOps, Smartsheet, or other similar project and work-management tools.

• Capable of defining delivery metrics and communicating status, risks, decisions, and forecasts to technical teams and senior leadership.

• Excellent skills in facilitation, organization, written communication, stakeholder management, and conflict resolution.

• Must be able to pass a background check prior to becoming a final candidate.

🏝️ Benefits

• Comprehensive health insurance starting on the first day of employment.

• 401K plan (US) with employer match: 1:1 for the first 3% of contributions and 0.5:1 for the next 2%; pre-tax and Roth options available; eligible the first of the month following 90 days of employment; immediately vested.

• RRSP (CAN) with employer match: 1:1 for the first 3% of contributions and 0.5:1 for the next 2%; pre-tax and Roth options available; eligible the first of the month following 90 days; immediately vested.

• Flexible paid time off: unlimited paid leave.

• 12 weeks of paid parental leave for all employees.

• Monthly remote work stipend of $75 USD / $140 CAD for phone and internet expenses.

• Generous holiday schedule.