Project Delivery Director - Fare Payment Modernization

Masabi

8d•Remote

About The Position

Masabi is seeking an experienced Project Delivery Director to lead end-to-end implementation of a major, multi-year transit technology modernization program in North America. The hands-on delivery leadership role brings together a complex, multi-vendor transformation involving account-based ticketing, contactless payments, integrations with existing and new technology infrastructure, customer-facing digital services, phased production deployment, legacy-system migration, and operational transition. The director will shape the baseline plan, establish governance, onboard partners, and translate program objectives and contract commitments into a delivery plan. They will coordinate internal and external teams, manage dependencies, and work through challenges with partners to deliver each phase successfully. This is an individual-contributor position, approximately 70% hands-on delivery leadership and 30% program leadership. The director leads the program independently, participates in the executive steering group, and represents Masabi in senior-level discussions. The role reports to the VP Strategic Programs and is available remotely to candidates based in Eastern Canada.

Requirements

Many years of senior program or delivery leadership delivering complex technology programs.
Personal end-to-end ownership, as the accountable program lead, of at least one large, multi-year systems implementation from mobilization through go-live and handover; workstream or project-level ownership within another program does not meet this requirement.
Experience setting up a program from day one, including the baseline plan, governance, and partner onboarding.
Track record of bringing vendors, integrators, suppliers, and customer teams together around a shared plan and ensuring partners meet their commitments.
Comfort with 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.
Commercial acumen, including program budgets, contractual deliverables, supplier performance, and change control.
Ability to build trust with senior customers and partners through clear communication and thoughtful negotiation.
Hands-on approach, steadiness under pressure, sound judgment, and the ability to hold firm when needed while knowing when to involve others.
Curiosity about AI tools and some experimentation with them; professional experience using AI tools is not required.

Nice To Haves

Experience in transit, fare collection, or payments; banking and SaaS backgrounds are also welcome.
Experience with contactless payments, payment gateways, acquiring, certification, and financial reconciliation.
Experience integrating software platforms with physical devices such as validators, fare gates, ticket vending machines, or other field equipment.
Experience with large public-sector technology modernization programs.

Responsibilities

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; manage the critical path, priorities, and interdependencies.
Translate contractual milestones into clear commitments, owners, and acceptance criteria.
Identify risks early and agree on recovery plans when milestones are at risk.
Coordinate software, hardware, and third-party integrations, including APIs, payment services, field equipment, and customer-facing platforms.
Work with engineering, product, architecture, QA, and implementation teams to sequence design, integration, and testing appropriately.
Resolve cross-vendor dependencies and technical blockers before they delay testing.
Align Masabi, subcontractors, technology and payment partners, and the customer around a shared delivery plan.
Set ownership, commitments, and escalation paths, and follow up to ensure partners deliver on time and to the required quality.
Build working relationships across organizations with different priorities and obligations.
Oversee system and user acceptance testing, defect resolution, and readiness reviews.
Coordinate phased deployments and ensure technical, operational, customer-service, and third-party teams are ready.
Plan legacy coexistence, account migration, cutover, reconciliation, and stabilization.
Base go-live decisions on evidence, agreed readiness criteria, and contingency plans, then guide the transition into hypercare and ongoing support.
Control scope, schedule, resources, budget, risks, issues, and changes.
Track subcontractor performance and support commercial commitments and change requests.
Provide accurate forecasts and clear, concise reporting to support timely leadership decisions.
Participate in the program’s executive steering group and represent Masabi in senior conversations.
Turn lessons from prior programs into improved practices through playbooks, coaching, or program standards.

Benefits

20 days of vacation per year in addition to public holidays, with the option to buy 5 additional days annually.
Office closure between Christmas and New Year; the posting describes total annual vacation as 28+ days.
Private healthcare and life insurance via Trinet.
Monthly team bonding allowance.
Up to CAD$1,300 per year for training.
CAD$325 per year for a home office.
CAD$50 per month for team building.
Menopause support.
Choice of a workstation.
Ability to work from any country in the world for up to 3 months per year.
Enhanced family leave.