Managing Director, Strategic Initiatives, Transformation & PMO

Florida Cancer Specialists•Florida - Remote, FL

4d•Remote

About The Position

The Managing Director, Strategic Initiatives, Transformation & PMO serves as an enterprise execution partner to the Chief Executive Officer and Executive Leadership Team (ELT), responsible for translating approved strategic priorities into coordinated enterprise execution. The role leads the Enterprise Transformation Office (ETO) and Program Management Office (PMO), overseeing portfolio governance, prioritization, organizational transformation, executive governance processes, enterprise change management standards, and strategic initiative execution. The position ensures enterprise initiatives are appropriately governed, resourced, sequenced, monitored, and aligned to organizational priorities while supporting successful implementation and benefit realization. The role partners with business leaders, functional teams, Business Development, diligence teams, a separate integration team, and operational stakeholders to coordinate execution, manage dependencies, monitor risks, support organizational readiness, and facilitate successful implementation from planning through stabilization. The position operates with a high degree of independence, discretion, and influence and achieves results primarily through collaboration, facilitation, governance, accountability, and executive stakeholder management rather than direct organizational authority. Business leaders retain ownership of operational decisions, business outcomes, and benefit realization; this role owns governance, visibility, coordination, accountability processes, escalation, and execution support.

Requirements

Bachelor's degree in business administration, healthcare administration, organizational leadership, operations management, or a related field; or an equivalent combination of education and progressive work experience.
10+ years of progressive leadership experience in enterprise transformation, strategic initiative execution, portfolio governance, PMO leadership, organizational change management, or large-scale operational transformation.
Demonstrated experience establishing or leading an Enterprise Transformation Office, PMO, or comparable governance function.
Proven success leading enterprise-scale implementations, organizational transformations, large technology deployments, integration initiatives, operational improvement programs, or complex cross-functional initiatives.
Experience coordinating execution across multiple executive leaders and business functions without direct authority.
Experience developing executive-level reporting, board materials, governance processes, and performance dashboards.
Demonstrated success influencing executive stakeholders and driving accountability through governance, facilitation, and relationship management.
Experience managing highly confidential leadership, organizational, board, and strategic initiative matters.
Enterprise transformation leadership, portfolio governance, prioritization, program management, project management, and benefit-realization governance.
Ability to convert approved strategic priorities into clear, sequenced, resourced, and measurable execution plans.
Demonstrated ability to lead complex enterprise initiatives through influence, facilitation, governance, accountability, and executive stakeholder management rather than direct organizational authority.
Executive-level written communication, presentation development, board-material preparation, and reporting capability.
Strong facilitation, conflict-resolution, and stakeholder-management skills for executive, physician, clinical, and cross-functional settings.
Strong analytical, critical-thinking, problem-solving, risk-management, and escalation judgment.
Ability to prioritize and advance multiple concurrent initiatives under deadline in a fast-changing, regulated environment.
Discretion, sound judgment, professionalism, and unquestioned integrity in handling confidential information.
Proficiency with project, collaboration, and dashboarding tools, including Smartsheet and Microsoft 365 applications such as Excel, PowerPoint, Word, Teams, and SharePoint.

Nice To Haves

Master's degree (MBA, MHA, MPH, or equivalent).
PMP, PgMP, Lean/Six Sigma, Prosci, CCMP, and/or an equivalent project, program, process-improvement, or change-management certification.
Healthcare, oncology, physician practice, health system, or other complex, highly regulated industry experience strongly preferred.
Experience supporting organizational change and adoption across geographically distributed organizations.

Responsibilities

Lead the Enterprise Transformation Office (ETO) and Program Management Office (PMO), establishing governance processes, methodologies, tools, reporting standards, and execution disciplines across the organization.
Own governance of the enterprise portfolio of approved strategic initiatives, ensuring alignment with organizational priorities, available capacity, resource constraints, dependencies, and timelines.
Facilitate enterprise prioritization processes and support annual and ongoing strategic planning activities by coordinating inputs, documenting decisions, translating priorities into implementation plans, and monitoring execution.
Develop enterprise portfolio dashboards, executive reports, scorecards, and performance metrics to provide visibility into initiative status, risks, dependencies, milestones, and outcomes.
Establish and enforce governance standards requiring defined business ownership, milestones, resource plans, risk assessments, dependency management, success metrics, and recovery actions for major initiatives.
Monitor initiative progress and benefit-realization plans while ensuring accountable business leaders retain ownership of operational decisions, business outcomes, and realized benefits.
Support execution of approved strategic priorities through stakeholder alignment, initiative coordination, dependency management, readiness planning, issue resolution, and progress monitoring.
Directly manage select CEO-sponsored strategic initiatives while coordinating execution support for broader enterprise initiatives led by accountable business owners.
Facilitate cross-functional collaboration across operational, clinical, administrative, and technology teams to advance approved organizational priorities.
Identify execution barriers, resource constraints, competing priorities, and implementation risks, and work with business leaders to develop mitigation and recovery plans.
Challenge insufficient plans and elevate unresolved risks, resource constraints, or missed commitments to the CEO and ELT while preserving business-leader accountability for outcomes.
Coordinate executive governance processes, leadership operating cadences, decision tracking, accountability reviews, and enterprise follow-through mechanisms in partnership with the CEO, ELT, and business leaders.
Support agenda development, content preparation, meeting coordination, action management, and follow-through for ELT, Leadership Team, Extended Leadership Team, and other executive governance forums.
Ensure executive decisions are clearly documented, communicated, assigned, tracked, and monitored through completion.
Provide executive leadership with transparent updates regarding initiative status, organizational risks, execution challenges, and enterprise dependencies.
Coordinate board governance activities, executive reporting processes, and board material preparation in partnership with the CEO, executive leadership, legal counsel, and functional leaders.
Contribute to the development of board presentations, executive summaries, implementation updates, and strategic initiative reporting.
Maintain rigorous standards for quality, consistency, version control, confidentiality, and timeliness of executive and board materials.
Coordinate governance, milestone oversight, dependency management, and readiness activities supporting strategic affiliations, partnerships, technology implementations, organizational transformations, and other enterprise initiatives.
Serve as the program-management bridge among Business Development, functional diligence teams, the separate integration team, and operational leaders to support the transition from Business Development through diligence and execution toward go-live.
Support the integration team through implementation, go-live readiness, stabilization, and benefit-realization governance without assuming transaction leadership, functional diligence ownership, or day-to-day integration ownership.
Monitor organizational readiness and implementation preparedness across impacted departments and stakeholders.
Support post-implementation stabilization and ensure lessons learned are captured and applied to future initiatives.
Establish and maintain enterprise change-management standards, methodologies, frameworks, tools, and governance processes.
Assess organizational readiness and adoption risks associated with major enterprise initiatives.
Ensure major initiatives include effective stakeholder engagement, communication, training, readiness, and adoption plans.
Partner with business leaders, Human Resources, Communications, Learning & Development, and project teams to support local execution and adoption of organizational change.
Track and report change-management effectiveness and readiness indicators across major transformation efforts.
Partner with executive and business leaders to coordinate and contribute to enterprise communications, leadership messaging, organizational announcements, stakeholder engagement, and change-management communications related to strategic initiatives.
Support development of town hall materials, executive talking points, leadership presentations, implementation updates, and transformation-related communications.
Facilitate alignment across stakeholders with competing priorities, perspectives, and interests.
Lead primarily through influence and matrix management, with a limited number of direct reports as organizational needs require.
Coach leaders and project sponsors in governance, accountability, execution discipline, change leadership, and transformation management.
Maintain confidentiality regarding strategic initiatives, leadership matters, organizational changes, legal matters, board activities, and other sensitive information.
Negotiate priorities, resolve issues, and explore solutions with physician and clinical leaders.
Perform other duties and projects as assigned.