Program Manager

a large-scale decommissioning initiative to retire six legacy applications that have supported business operations for more than 70 years. This program requires a senior program manager capable of navigating deeply intertwined legacy systems, coordinating diverse stakeholder groups, and driving a structured approach to risk, sequencing, and progress reporting. This is a highly cross-functional effort involving engineering, product, operations, sales, and marketing teams.
Key Responsibilities
Lead the end-to-end planning, execution, and delivery of a multi-year legacy systems decommissioning program.
Manage complex program dependencies across decentralized systems, including PowerBuilder applications and hardware-based solutions.
Partner closely with engineering, architecture, and product teams to assess technical trade-offs and ensure high-quality decision-making.
Coordinate two-week sprint planning, backlog prioritization, program reporting, and overall program hygiene.
Establish and maintain clear communication channels with a matrixed group of stakeholders across business and technology.
Evaluate program risks, create mitigation plans, and provide transparent updates to leadership.
Guide the unraveling of historical system integrations and support teams in untangling undocumented dependencies.
Drive alignment on phased decommission sequencing while managing constraints around concurrent work.
Utilize program management tools to track milestones, resources, and progress across multiple workstreams.
Support organizational change management efforts as systems transition or sunset.
Required Skills & Experience
10+ years of program management experience with large-scale technology initiatives.
Experience managing decommissioning, modernization, or transformation programs involving multiple legacy systems.
Strong understanding of cloud and software architecture principles, including AWS microservices, event-driven systems, REST APIs, CI/CD, and modern integration patterns.
Familiarity with mainstream data stores such as Postgres.
Ability to operate in environments with high ambiguity and evolving plans.
Proven strength in cross-functional leadership, stakeholder negotiation, and executive communication.
Experience guiding teams through complex architectural and operational trade-offs.
Deep proficiency with program management tools and agile methodologies.


Benefits:

York Solutions Offers a generous benefits package for eligible full-time employees:

• BCBS Medical with 3 Plans to choose from (PPO and High deductible PPO plans with Health Savings Program)
  
• Delta Dental plan with 2 free cleanings and insurance discounts
  
• Eye Med Vision with annual check-ups and discounts on lens
  
• Life and Accidental Death Insurance paid by company
  
• John Hancock 401(k) Retirement Plan with discretionary company match
  
• Voluntary Insurance programs such as: Hospital Indemnity, Identity Protection, Legal Insurance, Long Term Care, and Pet Insurance.
  
• Flexible work environment with some remote working opportunities
  
• Strong fun and teamwork environment
  
• Learning, development, and career growth