Senior Lead Enterprise Program Manager (RapidScale)

The Senior Lead Enterprise Program Manager is accountable for the orchestration and successful delivery of large-scale, complex cloud transformation programs.  

The role is a critical resource that bridges the gap between pre-sales team and post sales/delivery teams, including partnering closely with Engineering, Architecture, Operations, Delivery, and Customer Success teams to drive technical program execution, mitigate risk, and ensure seamless delivery for enterprise clients undergoing major cloud transformations. 

You will lead multiple concurrent programs (typically $10M–$50M+), establish program governance, manage executive stakeholders, and ensure technical and commercial outcomes are achieved. The ideal candidate combines deep program management expertise with strong technical acumen in VMware, hybrid cloud, and infrastructure modernization. 

Key Responsibilities 

• Lead complex cloud migration programs from planning through execution, including assessment, design, migration, validation, and stabilization phases. 

• Oversee all aspects of VMware-to-cloud migrations (vSphere, vSAN, NSX, Aria), ensuring alignment with architecture blueprints and enterprise standards. 

• Develop and manage comprehensive program plans, schedules, and budgets; track progress against milestones, dependencies, and deliverables. 

• Establish and enforce program governance and decision gates to manage scope, quality, risk, and change control. 

• Collaborate cross-functionally with engineering, architecture, security, finance, and operations teams to drive alignment and accountability. 

• Serve as the primary customer interface, facilitating steering committees, executive briefings, and program-level reporting. 

• Identify and proactively manage and document program risks and issues, ensuring mitigation strategies are defined and executed. 

• Partner with Finance and Operations to manage program financials, forecasts, and variance reporting. 

• Drive continuous improvement through the development of repeatable migration frameworks, playbooks, and delivery templates. 

• Mentor and coach project managers and technical leads to elevate overall program management maturity within the organization. 

• Engage and manage third-party vendors, partners, and hyperscaler alliances to ensure delivery excellence. 

Required / Minimum Qualifications 

• Bachelor’s degree in a related discipline and 10+ years’ experience in program or project management within IT, cloud, or professional services environments. 

• PMP or equivalent certification (or demonstrable equivalent experience). 

• Proven experience leading large, complex cloud or data center migration programs ($10M+), including multi-region and multi-tower initiatives. 

• Demonstrated success in governing enterprise-scale programs, including risk, change, and stakeholder management. 

• Expertise in program financial management including budgeting, forecasting, and variance analysis. 

• Exceptional communication and executive presentation skills, with the ability to distill complex technical information into business-oriented narratives. 

Preferred / Nice-to-Have Qualifications 

• Experience in data center exit, data center consolidation, or M&A IT integration programs. 

• Experience with Walk-in Takeover ( WITO) or similar transaction models is a strong plus.  

• Background in Managed Services Provider (MSP), Cloud Service Provider (CSP), or Systems Integrator (SI) environments. 

• Familiarity with service transition frameworks (ITIL, SIAM) and delivery excellence practices. 

• Experience managing global, distributed delivery teams and vendor ecosystems. 

• Experience operating within a Transition & Transformation function or Office of the CTO is a plus.