Director of Strategic Initiatives

Role Description

As the Director of Strategic Initiatives, you will serve as a key partner to the Chief Transformation Officer and help turn enterprise strategy into disciplined execution. This role sits at the center of the transformation portfolio, ensuring strategic initiatives are prioritized, governed, and delivered in a way that creates measurable business impact.

• Lead the transformation PMO, providing structure and accountability across a complex portfolio of initiatives.
• Drive high-priority cross-functional programs from planning through execution.
• Blend of strategic thinking, operational leadership, program management expertise, and strong stakeholder influence across all levels of the organization.

Qualifications

• 5+ years of experience in operations, program management, project management, management consulting, transformation, or a related field.
• Bachelor's degree.
• Proven experience leading large, complex, cross-functional programs involving multiple workstreams and stakeholder groups.
• Demonstrated ability to translate strategic priorities into structured plans, execution roadmaps, sequencing recommendations, and delivery frameworks.
• Strong understanding of portfolio management, delivery governance, RAID management, stage-gates, dependency tracking, executive reporting, and decision support.
• Experience managing initiative risks, resource planning, and cross-functional coordination across strategic programs.
• Experience supporting organizational change and driving adoption of new processes, systems, or ways of working.
• Track record of partnering on value realization, business case development, benefit tracking, or operational performance measurement.
• Strong analytical, critical-thinking, and structured problem-solving capabilities.
• Excellent verbal, written, and executive communication skills.
• Strong relationship-building and stakeholder management skills with the ability to influence across multiple organizational levels.
• High ownership mindset with the ability to drive accountability, manage competing priorities, and deliver results in a fast-paced environment.

Requirements

• MBA (Valuable Addition).
• Experience leading a PMO, enterprise program management office, or transformation delivery function (Valuable Addition).
• Experience partnering directly with a Chief Transformation Officer, executive transformation leader, or similar executive sponsor (Valuable Addition).
• Experience supporting Board-level reporting, steering committees, or executive governance forums (Valuable Addition).
• Experience with enterprise transformation, operating model redesign, or large-scale organizational change initiatives (Valuable Addition).
• Background in value realization, financial impact measurement, or strategic portfolio management (Valuable Addition).
• Insurance industry experience (Valuable Addition).

Benefits

• Multiple medical plan options, with preventive care covered at 100%.
• Free virtual medical and mental healthcare for employees and their families, plus a dedicated healthcare concierge.
• Employer-paid short-term and long-term disability coverage.
• Paid parental leave.
• Personalized PTO that lets you take time away when you need it, without traditional accruals, plus separate sick leave.
• Competitive 401(k) company match to help you build your financial future.
• Comprehensive dental and vision coverage.
• Employee Assistance Program with confidential mental health, legal, financial, and work-life support.