Director of Strategic Initiatives

About the role

This role serves as a key partner to the Chief Transformation Officer and helps turn enterprise strategy into disciplined execution. The position sits at the center of the transformation portfolio, ensuring strategic initiatives are prioritized, governed, and delivered in a way that creates measurable business impact. The individual will lead the transformation PMO, provide structure and accountability across a complex portfolio of initiatives, and personally drive high-priority cross-functional programs from planning through execution. Success requires a blend of strategic thinking, operational leadership, program management expertise, and strong stakeholder influence across all levels of the organization.

Responsibilities

• Partner with the Chief Transformation Officer to translate strategic priorities into a structured, capacity-aware portfolio of enterprise initiatives.
• Lead and evolve the transformation PMO, establishing governance standards, delivery disciplines, reporting frameworks, and execution rhythms that drive consistent outcomes.
• Direct portfolio oversight by maintaining visibility into milestones, risks, dependencies, resourcing needs, and key decision points across strategic initiatives.
• Personally lead a select group of high-priority cross-functional initiatives, ensuring successful execution and sustainable business results.
• Identify and proactively resolve scope, schedule, dependency, and resource risks before they impact portfolio performance.
• Coordinate closely with Change Management, Communications, Data, Value Realization, and business leaders to align delivery, adoption, reporting, and measurable outcomes.

Requirements

• 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.

Preferred Qualifications

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

Schedule

This is a fully remote, full-time position.

Pay

Pay Range: $200,000—$250,000 USD. Any job offer is based upon a salary analysis to comply with applicable state pay transparency laws, considering relevant experience, education, certifications, and seniority as compared to others doing substantially similar work. Roles may also be eligible for supplemental compensation, such as performance-based bonus, commission, or equity.

Benefits

• Comprehensive medical, dental, and vision insurance with multiple plan options and 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) with company match.
• Employee Assistance Program with confidential mental health, legal, financial, and work-life support.