Director of Strategic Initiatives

About the Opportunity The Director of Strategic Initiatives serves as a key partner to the Chief Transformation Officer, helping turn enterprise strategy into disciplined execution. Operating at the center of the transformation portfolio, this fully remote, full-time role ensures strategic initiatives are prioritized, governed, and delivered to achieve measurable business impact. The role leads the transformation PMO, provides structure and accountability across a complex portfolio of initiatives, and personally drives high-priority cross-functional programs from planning through execution. Key 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. Required Qualifications Bachelor's degree.5+ years of experience in operations, program management, project management, management consulting, transformation, or a related field.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 Master of Business Administration (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.Experience within the insurance industry. Compensation and Benefits The base salary range for this role is $200,000 to $250,000 USD per year. 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. The organization offers a comprehensive benefits package, including: Medical, dental, and vision insuranceShort-term and long-term disability coveragePaid parental leavePaid time off, separate sick leave, and paid holidays401(k) retirement plan with company matchEmployee Assistance Program Equal Opportunity Employment The organization is an equal opportunity employer committed to diversity and inclusion in the workplace. Discrimination and harassment of any kind are prohibited based on race, color, sex, religion, sexual orientation, national origin, citizenship or immigration status, disability, genetic information, pregnancy, or any other protected characteristic outlined by federal, state, or local laws. This policy applies to all employment practices, including hiring, recruiting, promotion, termination, layoff, leave of absence, compensation, benefits, and training. Hiring decisions are based solely on qualifications, merit, and business needs.