Project Delivery Director - Fare Payment Modernization

Masabi • New York, NY

9d • Remote

About The Position

Masabi is seeking an experienced delivery leader to lead the end-to-end implementation of a major, multi-year transit technology modernization program in North America. The program includes 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 role begins with establishing the baseline plan, governance, and partner onboarding, then translating program objectives and contractual commitments into a clear delivery plan. The director coordinates internal and external teams, manages dependencies and challenges, and guides delivery through each phase. This is a hands-on role combining program management discipline with practical experience in complex technical implementations. It involves working closely with technical teams, subcontractors, and customer stakeholders, as well as representing Masabi in senior conversations and participating in the executive steering group. The role is an individual contributor position, with approximately 70% hands-on delivery leadership and 30% program leadership.

The position reports to the VP Strategic Programs and is available remotely to candidates based in the Eastern United States.

Requirements

• Many years of senior program or delivery leadership experience 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 another person'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 accountable to their commitments.
• Comfort 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 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, sound judgment, and confidence to make or escalate decisions appropriately.
• Curiosity about AI tools and some experimentation with them; 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 critical paths, 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; follow up to ensure partners meet agreed timing and quality standards.
• Build working relationships among 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.
• 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.
• Manage 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.
• Represent Masabi in senior conversations and participate in the program's executive steering group.
• Apply lessons from past programs to improve practices through playbooks, coaching, or setting program delivery standards.

Benefits

• 20 days of vacation per year, in addition to public holidays, with the option to buy 5 additional days annually; the office is also closed between Christmas and New Year, totaling more than 28 days of vacation.
• 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 home office expenses.
• 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 in the world.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed