Director of Strategic Execution & Transformation

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

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