Project Delivery Director - Fare Payment Modernization

About Masabi

At Masabi, we’re driving the fare payment revolution, powering the journeys of millions all over the world. We build fare collection platforms that allow riders to seamlessly buy and present tickets for public transport either on their mobile phones, from a ticket machine, or even by tapping their bank card to travel.

Our Justride platform is used in over 250 locations globally, including some of the largest cities in the world. With our industry-first mobile ticketing SDK, we’ve partnered with large players in the transport space, including Uber, Moovit, and Transit.

The Role

Masabi is seeking an experienced Lead Program Manager / Project Delivery Director to lead the end-to-end implementation and delivery of a major, multi-year transit technology modernization program in North America. This is a hands-on delivery leadership role bringing together a complex, multi-vendor technology transformation. The program involves account-based ticketing, contactless payments, integration with existing and new technology infrastructure, customer-facing digital services, phased production deployment, legacy system migration, and operational transition.

You’ll be there from the start, shaping the baseline plan, setting up governance, and bringing partners on board. From there, you’ll turn program objectives and contract commitments into a clear delivery plan, bring internal and external teams together, stay ahead of critical dependencies, and work through challenges with your partners so every phase lands well.

Reporting to our VP Strategic Programs, you’ll lead the program independently, be part of its executive steering group, and represent Masabi in senior conversations. This is an individual contributor role, with around 70% hands-on delivery leadership and 30% program leadership.

Note: This role is open to candidates based remotely in Eastern Canada.

Responsibilities

End-to-End Program Delivery

• Lead implementation from mobilization through design, integration, testing, rollout, migration, and handover.
• Own the integrated master schedule across internal teams, subcontractors, the customer, and third parties, keeping the critical path, priorities, and interdependencies on track.
• Turn contractual milestones into clear commitments, owners, and acceptance criteria.
• Spot risks early and agree on recovery plans with the team when milestones are at risk.

Technical Implementation and Systems Integration

• Coordinate software, hardware, and third-party integrations, including APIs, payment services, field equipment, and customer-facing platforms.
• Work closely with engineering, product, architecture, QA, and implementation teams so design, integration, and testing happen in the right order.
• Help clear cross-vendor dependencies and technical blockers before they impact delivery.

Multi-Vendor and Stakeholder Management

• Bring Masabi, subcontractors, technology and payment partners, and the customer together around one delivery plan.
• Set clear ownership, commitments, and escalation paths, ensuring partners deliver agreed scopes on time and to the right quality.
• Build strong working relationships with organizations that have varying priorities and obligations.

Testing, Deployment, and Operational Transition

• Oversee system and user acceptance testing, defect resolution, and readiness reviews.
• Coordinate phased deployments, ensuring technical, operational, customer-service, and third-party teams are aligned.
• Lead planning for legacy coexistence, account migration, cutover, reconciliation, and stabilization.
• Base every go-live on evidence, agreed readiness criteria, and contingency plans, guiding the move into hypercare and ongoing support.

Program Controls and Commercial Delivery

• Keep scope, schedule, resources, budget, risks, issues, and changes under control.
• Track subcontractor performance and support commercial commitments and change requests.
• Share accurate forecasts and concise reporting that enables executive decision-making.

About You

• Deep experience delivering complex technology programs, with substantial experience in senior program or delivery leadership.
• Personal, end-to-end ownership of at least one large, multi-year systems implementation as the accountable program lead from mobilization through go-live and handover.
• Proven experience establishing a program from day one: baseline plan, governance, and partner onboarding.
• Demonstrated track record aligning vendors, integrators, suppliers, and customer teams around a shared plan.
• Expertise handling 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 program budgets, contractual deliverables, supplier performance, and change control.
• Executive-level communication, negotiation, and stakeholder management skills.
• Habit of codifying learnings into playbooks, coaching, and repeatable standards.

Nice to Have

• Experience in transit, fare collection, or payments (banking and SaaS backgrounds are also welcomed).
• Knowledge of contactless payments, payment gateways, acquiring, certification, and financial reconciliation.
• Experience integrating software platforms with physical devices, validators, fare gates, ticket vending machines, or field hardware.
• Experience with large public-sector technology modernization programs.

Benefits

• 20 days of vacation per year (in addition to public holidays), plus the option to buy 5 additional days, and company shutdown between Christmas and New Year (totaling 28+ days off)
• Private Healthcare and Life Insurance via TriNet
• CAD $1,300 annual training budget
• CAD $325 annual home office allowance
• CAD $50 per month team building allowance
• Choice of workstation
• Ability to work up to 3 months per year from any country globally
• Enhanced family leave
• Menopause support