Project Delivery Director – Fare Payment Modernization

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

📋 Description

• Lead the implementation process from mobilization through design, integration, testing, rollout, migration, and handover.

• Manage the integrated master schedule involving internal teams, subcontractors, the customer, and third parties.

• Convert contractual milestones into explicit commitments, assign owners, and establish acceptance criteria.

• Proactively identify risks and develop recovery plans when milestones are at risk.

• Coordinate software, hardware, and third-party integrations, including APIs, payment services, field equipment, and customer-facing platforms.

• Collaborate with engineering, product, architecture, QA, and implementation teams during design, integration, and testing phases.

• Address cross-vendor dependencies and resolve technical blockers.

• Ensure alignment between Masabi, subcontractors, technology and payment partners, and the customer around a unified delivery plan.

• Establish ownership, commitments, escalation paths, and monitor partner delivery.

• Supervise system and user acceptance testing, defect resolution, and readiness reviews.

• Coordinate phased deployments and ensure readiness across technical, operational, customer service, and third-party teams.

• Lead planning for legacy coexistence, account migration, cutover, reconciliation, and stabilization.

• Base go-live on evidence, readiness criteria, and contingency plans, then oversee hypercare and ongoing support.

• Manage scope, schedule, resources, budget, risks, issues, and changes effectively.

• Monitor subcontractor performance and support commercial commitments and change requests.

• Provide forecasts and concise reporting to assist leadership decisions.

• Represent Masabi in senior-level discussions and engage in the executive steering group.

• Contribute to shaping Masabi’s strategy for large programs in North America.

⛳️ Requirements

• Extensive experience in delivering complex technology programs, with many years in senior program or delivery leadership roles.

• Personal, end-to-end accountability for at least one large, multi-year systems implementation as the program lead, from mobilization to go-live and handover.

• Proven experience in establishing a program from the outset: baseline plan, governance, and partner onboarding.

• Demonstrated success in uniting vendors, integrators, suppliers, and customer teams around a unified plan.

• Proficient in managing complex schedules, critical paths, resource plans, and recovery strategies.

• Practical understanding of software implementation, SaaS platforms, enterprise systems integration, APIs, technical testing, and production deployment.

• Strong commercial acumen, including awareness of program budgets, contractual deliverables, supplier performance, and change control.

• Credibility at the executive level, fostering trust with senior customers and partners through effective communication and negotiation.

• Experience in transit, fare collection, or payments is preferred.

• Familiarity with contactless payments, payment gateways, acquiring, certification, and financial reconciliation is advantageous.

• Experience integrating software platforms with physical devices, such as validators, fare gates, ticket vending machines, or other field equipment is a plus.

• Background in managing large public-sector technology modernization programs is beneficial.

• Candidates should be based in Eastern Canada.

• An interest in AI experimentation and a sense of curiosity are expected.

• CV in English is required for application.

🏝️ Benefits

• 20 days of vacation annually (in addition to public holidays), with the option to purchase an additional 5 vacation days each year.

• Office closure between Christmas and New Year, totaling over 28 days of vacation.

• Private Healthcare and Life Insurance provided through Trinet.

• Monthly team bonding allowance.

• Up to CAD$1300 training budget per year.

• CAD$325 annually to invest in your home office.

• CAD $50 per month for team-building activities.

• Support for menopause-related issues.

• Choice of workstation.

• Opportunity to work remotely for up to 3 months each year from any country worldwide.

• Enhanced family leave policies.