Project Delivery Director - Fare Payment Modernization

Masabi•New York, NY

8d•Remote

About The Position

Masabi is seeking an experienced 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 hands-on delivery leadership role brings together a complex, multi-vendor transformation involving 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. The director will shape the baseline plan, establish governance, onboard partners, and turn program objectives and contractual commitments into a clear delivery plan. They will coordinate internal and external teams, manage critical dependencies, and address delivery challenges with partners. The role calls for strong program management discipline and practical experience leading complex technical implementations end to end; it is not governance-only. Reporting to the VP Strategic Programs, the director will lead the program independently, participate in its executive steering group, and represent Masabi in senior conversations. This is an individual contributor role, approximately 70% hands-on delivery leadership and 30% program leadership. The position is remote for candidates based in the Eastern United States.

Requirements

Many years of experience in 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 leadership within someone else’s program does not meet this requirement.
Experience establishing a program from day one, including the baseline plan, governance, and partner onboarding.
A track record of aligning vendors, integrators, suppliers, and customer teams around a shared plan and holding partners to 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 judgment, 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, and sound judgment about when to make decisions and when to involve others.
Experience experimenting with AI tools and curiosity about how they can support learning, problem-solving, and effective work; professional AI-tool experience is not required.

Nice To Haves

Experience in transit, fare collection, or payments; banking and SaaS backgrounds are also welcomed.
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 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 one delivery plan.
Establish 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 differing 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.
Lead planning for legacy coexistence, account migration, cutover, reconciliation, and stabilization.
Base go-live decisions on evidence, agreed readiness criteria, and contingency plans; guide 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 help leaders make timely decisions.
Represent Masabi in senior conversations and participate in the executive steering group.
Apply lessons from past programs to improve ways of working through playbooks, coaching, or program standards.

Benefits

20 days of vacation per year in addition to public holidays, with the option to buy an additional 5 days each year.
Office closure between Christmas and New Year, bringing stated annual vacation to 28+ days.
Private healthcare and life insurance via Trinet.
Menopause support.
Training allowance of up to $1,000 per year.
Choice of a workstation.
$250 per year for a home office.
Ability to work from any country in the world for up to 3 months per year.
Enhanced family leave.
Fun and collaborative environment focused on making a difference.