Project Delivery Director - Fare Payment Modernization

About Us_ // 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.  Your own journey is important to us too. Choosing a role here means joining a network of innovators from all walks of life; a group of passionate individuals who consistently deliver. Here, you’ll find the tools you need to build the career you want. Whether you’re taking the direct route or trying a new path, we’ll support you no matter what.  The Role_ // Masabi is seeking an experienced Lead Program Manager 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. We’re looking for a delivery leader who combines strong program management discipline with practical experience of complex technical implementations end to end. This isn’t a governance-only role. You’ll be comfortable moving between strategy and detail, working closely with technical teams, subcontractors and customer stakeholders to keep delivery moving. 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. This role offers a chance to shape how Masabi runs large programs in North America, on a flagship program that will set the standard for how we deliver moving forward. Location_ // This role is available in a remote model for candidates based 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 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 slow testing down. 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, and follow up so partners deliver what they’ve agreed, on time and to the right quality. - Build strong working relationships with organizations that have different priorities and obligations. Testing, deployment and operational transition - Oversee system and user acceptance testing, defect resolution and readiness reviews. - Coordinate phased deployments, making sure technical, operational, customer-service and third-party teams are ready. - Lead planning for legacy coexistence, account migration, cutover, reconciliation and stabilization. - Base every go-live on evidence, agreed readiness criteria and contingency plans, then guide 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 clear, concise reporting that helps leaders make timely decisions. About You - Deep experience delivering complex technology programs, with many years 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 (not a workstream or project inside someone else’s program), from mobilization through go-live and handover. - Experience setting up a program from day one: the baseline plan, governance and partner onboarding. - A track record of bringing vendors, integrators, suppliers and customer teams together around one shared plan, and keeping partners true to what they’ve agreed. - Comfortable 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. - Great commercial sense, including program budgets, contractual deliverables, supplier performance and change control. - Credibility at executive level, building trust with senior customers and partners through clear communication and thoughtful negotiation. - A habit of turning lessons from past programs into better ways of working for others, whether through playbooks, coaching or setting the standard for how programs are run. - Hands-on and steady under pressure, with the quiet confidence to hold firm when it matters, and sound judgment about when to make the call and when to bring others in. Nice to Have_ - Experience in transit, fare collection or payments. Banking and SaaS backgrounds are very welcome too. - Contactless payments, payment gateways, acquiring, certification and financial reconciliation. - Integration of software platforms with physical devices, validators, fare gates, ticket vending machines or other field equipment. - Large public-sector technology modernization programs. AI at Masabi_ // AI is becoming part of how we work at Masabi. You don’t need professional experience using AI tools, but we’d expect you’ve experimented with them and are curious about how they can help you learn, solve problems, and work more effectively. Some Of Our Benefits_ • 20 days of vacation per year (in addition to public holidays), plus the option to buy an additional 5 days of vacation each year. On top of this, our office is shut every year between Christmas and New Year, totalling a whopping 28+ days of vacation • Private Healthcare and Life Insurance via Trinet • Monthly team bonding allowance • Up to CAD$1300 training bugdet per year • CAD$325 per year to spend on your home office • CAD $50 per month team building • Menopause support • Choice of a workstation • Ability to work for up to 3 months per year from any country in the world • Enhanced family leave   Careers at Masabi are for people going places - driven by a mission to make transit fair and accessible for all. // We are a network of innovators from all walks of life, passionate about making a difference. At Masabi, we operate with openness and trust, creating an environment where everyone feels empowered to bring their whole, authentic selves to work. Whoever you are, just be yourself. // We welcome applications from underrepresented groups, including disabled and neurodivergent people, and can make adjustments at any stage of the process. You’re also welcome to share your pronouns whenever you feel comfortable. Together, we simplify journeys, remove barriers, and improve daily life for millions. Why Join Masabi? - Driven by Purpose – We believe in journeys made simple. The work isn’t always easy, but the best things never are. - Encouraged to Accelerate – Masabi is going places and our people are in the driving seat. Whether you’re taking the direct route or exploring new paths, we support your journey. - Advancing with Empathy – We put people first and foster a culture of learning, not blame. No matter your cargo, we share the load. We’re already powering journeys - are you ready to join us?