Demo

Director of Strategic Execution & Transformation

Piper Companies
Piper Companies Salary
Frederick, MD Full Time
POSTED ON 4/18/2026
AVAILABLE BEFORE 5/17/2026
Piper Companies is looking for a Director of Strategic Execution & Transformation to join a thriving insurance company to serve as a central coordination point across product, transformation, and portfolio activities, ensuring leadership priorities translate into clear plans, consistent progress, and effective decision-making . This is a hybrid position and requires the candidate to be onsite 3 days a week.

Essential Duties of the Director of Strategic Execution & Transformation:

  • Execute and oversee strategic initiatives by translating leadership priorities into actionable plans, tracking progress, surfacing risks early, and escalating issues with clear recommendations
  • Maintain leadership operating rhythm and governance by coordinating steering committees, portfolio reviews, executive updates, and ensuring follow-through on decisions and commitments
  • Provide executive-ready communications by developing concise presentations, narratives, and visual storytelling that translate complex initiatives into clear decision-making insights
  • Ensure portfolio visibility and PMO alignment by maintaining an integrated view of initiatives, improving reporting and governance, and coordinating with PMO and program leaders
  • Drive cross-team execution and problem solving by aligning stakeholders across technology and business teams, removing barriers, and resolving operational challenges to sustain momentum

Qualifications of the Director of Strategic Execution & Transformation:

  • Bachelor's degree preferred but not required
  • 10 years of experience in strategy, transformation, consulting, program leadership, or enterprise PMO environments
  • Working knowledge of portfolio governance, program management methodologies, and organizational operating rhythms used in large technology organizations
  • Strong analytical capability with the ability to synthesize large volumes of information into actionable insights
  • Experience preparing executive-level communications including presentations, leadership updates, and governance materials

Compensation for the Director of Strategic Execution & Transformation:

  • $200,000 - $220,000 bonus (based on experience)
  • Comprehensive benefit package; Cigna Medical, Cigna Dental, Vision, 401k w/ ADP, PTO, paid holidays, sick Leave as required by law

This job opens for applications on 4/6/26. Applications for this job will be accepted for at least 30 days from the posting date

Strategic initiatives, initiative execution, transformation leadership, technology transformation, execution management, action planning, milestone tracking, outcome delivery, strategic alignment, priority execution, initiative ownership, delivery leadership, accountability, risk management, issue identification, early risk surfacing, dependency management, cross-team coordination, escalation management, decision support, leadership escalation, operating model, governance forums, leadership governance, steering committees, portfolio reviews, executive updates, executive readiness, meeting preparation, agenda management, decision tracking, action tracking, follow-up management, commitment tracking, operating cadence, operating rhythm, program cadence, execution discipline, executive communications, executive storytelling, strategic narratives, leadership presentations, board-level materials, transformation updates, portfolio communications, visual storytelling, decision enablement, clarity of messaging, complex initiative translation, alignment messaging, enterprise communication, portfolio visibility, initiative portfolio, integrated portfolio view, portfolio oversight, transformation portfolio, technology portfolio, portfolio management, PMO coordination, program management office, program governance, initiative structuring, progress tracking, status reporting, risk reporting, portfolio reporting, governance frameworks, oversight mechanisms, cross-functional execution, stakeholder alignment, stakeholder management, product collaboration, engineering collaboration, IT operations alignment, infrastructure coordination, cybersecurity coordination, business partnership, barrier removal, issue resolution, operational problem solving, delivery momentum, timeline alignment, deliverable management, change execution, enterprise transformation, strategic delivery, execution governance, leadership enablement

Salary.com Estimation for Director of Strategic Execution & Transformation in Frederick, MD
$174,650 to $229,948
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