Senior Manager – Project Program Management

This is a fully remote position, open to applicants in Connecticut.

📋 Description

• Lead and manage intricate, multi-workstream transformation and operational initiatives across the organization.

• Convert strategic goals into a comprehensive program roadmap.

• Ensure alignment among interrelated projects and workstreams.

• Oversee program-level milestones, dependencies, risks, decisions, governance, and benefits.

• Deliver executive-ready visibility into progress and results.

• Create structures and operating rhythms to maintain alignment among interconnected efforts.

• Guide programs from definition and planning phases through implementation and stabilization.

• Collaborate with project and workstream leaders on scope, timelines, resources, readiness, and deliverables.

• Identify barriers and tradeoffs across projects, drive issue resolution and escalation, and facilitate decision-making.

• Establish and oversee program governance, decision-making forums, escalation paths, and operational rhythms.

• Maintain program-level RAID (Risks, Assumptions, Issues, Dependencies) management.

• Assess program health using integrated milestones, performance indicators, and outcome measures.

• Compile status, risks, interdependencies, decisions, and outcome signals into executive reports.

• Develop executive-ready updates linking workstream activities to program objectives and business results.

• Collaborate with sponsors, project leaders, and functional leaders to align priorities and address delivery risks.

• Facilitate cross-functional discussions across business, product, technology, and operations teams.

• Present program health, dependencies, decisions, risks, mitigation strategies, and outcomes to senior leadership.

• Influence stakeholders without direct authority and foster shared accountability.

• Coordinate implementation readiness, handoffs, release/go-live dependencies, and stabilization requirements.

• Supervise program-level issue triage, dependency management, and readiness planning.

• Define and monitor program outcomes, value measures, and benefits realization.

⛳️ Requirements

• 8-10 years of experience in project management, program management, PMO, or a related field with increasing responsibility in complex, cross-functional programs.

• PMP, PgMP, or a similar certification.

• Proven experience leading programs composed of multiple interdependent projects or workstreams from planning to implementation and stabilization.

• Expertise in developing integrated program roadmaps and managing cross-project milestones, dependencies, risks, decisions, delivery sequencing, and outcome measures.

• Experience in establishing or supporting program governance, executive reporting, escalation, and leadership decision-making.

• Background in creating executive-facing program materials, integrated reports, dashboards, decision papers, and strategic summaries for senior leadership.

• Skill in translating ambiguous or emerging business needs into program structures, governance, scalable tools, operating approaches, and execution practices.

• Experience coordinating across business, project, product, technology, and operational stakeholders.

• Ability to identify systemic delivery gaps, cross-project dependencies, and program risks.

• Proven track record in defining and tracking program outcomes, value measures, benefits, or other indicators of realization.

• Strong analytical, organizational, strategic planning, and problem-solving capabilities.

• Extensive knowledge of Agile, Waterfall, and Hybrid project management methodologies.

• Proficient in Microsoft Project (MPP), Jira, Asana, Smartsheet, Monday.com, and similar platforms.

• Advanced proficiency in Microsoft Office Suite, including Excel, PowerPoint, Word, and Teams.

• Familiarity with Miro, Mural, Microsoft Whiteboard, or similar collaboration and digital whiteboarding tools.

• Strong systems thinking and business acumen.

• Ability to influence cross-functional leaders and drive alignment without direct authority.

• Exceptional verbal and written communication skills.

• Capable of navigating ambiguity and structuring complex programs.

• Ability to represent program health, decisions, risks, and outcomes in senior leadership and governance contexts.

• Bachelor’s degree required, or equivalent experience, preferably in Business, Healthcare Administration, Operations Management, or a related field.

🏝️ Benefits

• Medical coverage.

• Dental coverage.

• Vision coverage.

• Paid time off.

• Retirement savings options.

• Wellness programs.

• Additional resources supporting physical, emotional, and financial well-being.

• CVS Health bonus, commission, or short-term incentive program.

• Award target in the company’s equity award program.