Director of Strategic Execution & Transformation

Director, Strategic Execution & Transformation

Department: IT & Transformation

Location: Frederick, Maryland

Reports to: VP, Transformation & Engineering

Role Summary

Zachary Piper is Seeking a Director of Strategic Execution & Transformation to drive execution of the organization’s highest‑priority Transformation and Technology initiatives. Partnering with the VP of Business Transformation & Engineering, this role ensures leadership priorities are converted into executable plans, tracked rigorously, and advanced through effective governance, communication, and cross‑team coordination.

The role serves as a central point of coordination across product, technology, transformation, and PMO functions to maintain initiative momentum, surface risks, and support executive decision-making.

Key Responsibilities

Strategic Initiative Execution

• Drive execution of prioritized Transformation and Technology initiatives.
• Translate leadership priorities into clear plans, milestones, and outcomes.
• Maintain end‑to‑end visibility into initiative progress, risks, and dependencies.
• Partner with initiative owners to ensure accountability and delivery.
• Escalate risks and decision needs with clear analysis and recommendations.

Leadership Governance & Operating Rhythm

• Prepare steering committees, portfolio reviews, and executive updates.
• Ensure initiative owners provide decision‑ready updates and risk assessments.
• Track leadership actions and ensure timely follow‑through.
• Maintain a consistent governance and execution cadence across initiatives.

Executive Communication

• Develop executive‑level presentations, updates, and portfolio materials.
• Translate complex initiatives into clear, concise messaging for senior leaders.
• Ensure consistent, structured communication across transformation efforts.

Portfolio & PMO Coordination

• Maintain an integrated view of the Transformation & Technology portfolio.
• Coordinate with PMO and program leaders on structure, tracking, and reporting.
• Improve portfolio reporting and governance to support leadership oversight.

Cross‑Functional Coordination

• Work across product, engineering, IT operations, infrastructure, cybersecurity, and business teams.
• Align stakeholders on priorities, timelines, and deliverables.
• Remove execution barriers and coordinate resolution of delivery issues.

Qualifications

Education / Knowledge

• Bachelor’s degree in business, technology, engineering, finance, or equivalent experience.
• Strong understanding of technology organizations and enterprise transformation.
• Knowledge of portfolio governance, program management, and executive reporting.
• Experience translating strategy into executable initiatives.

Experience

• 10+ years in strategy, transformation, consulting, program leadership, or enterprise PMO roles.
• Proven delivery of complex, cross‑functional initiatives.
• Regular interaction with executive leadership.
• Experience operating in matrixed organizations without direct authority.
• Strong background in executive presentations and governance materials.

Skills

• Structured problem solving and analytical thinking.
• Executive‑level communication and visual storytelling.
• Stakeholder influence and coordination skills.
• Ability to manage ambiguity and drive execution.
• Advanced PowerPoint skills.
• High professional judgment and discretion.

Travel

Up to 10%

Compensation

Salary: $150,000 - $225,000

Benefits: PTO, Paid Holidays, Medical, Dental, Vision, 401(k), Sick Leave (As required by law), & 20% bonus. 

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Strategic execution, business transformation, technology transformation, initiative execution, portfolio management, enterprise PMO, program governance, executive governance, leadership operating rhythm, steering committees, portfolio reviews, executive reporting, cross‑functional execution, stakeholder alignment, matrixed organizations, initiative accountability, risk management, issue escalation, decision support, executive communications, executive presentations, strategic narrative, visual storytelling, PowerPoint expertise, portfolio visibility, PMO coordination, delivery oversight, operating cadence, transformation programs, organizational change, technology governance, product and engineering collaboration, IT operations, infrastructure, cybersecurity, ambiguity management, problem structuring, milestone tracking, senior leadership interaction