Director of Strategic Initiatives
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Job Description
Director leading Patriot’s enterprise transformation PMO and strategic initiatives for a national insurance services firm. Driving governance, cross-functional execution, executive reporting, and measurable business impact.
Responsibilities:
- Partner with the Chief Transformation Officer to translate strategic priorities into a structured, capacity-aware portfolio of enterprise initiatives
- Recommend prioritization, sequencing, and trade-offs based on strategy, resource capacity, dependencies, and risk
- Own the transformation PMO, including its mandate, delivery standards, governance model, and overall output
- Lead the PMO Senior Manager and team, ensuring cadence, RAID discipline, stage-gates, reporting, and portfolio tracking
- Maintain a single source of truth for portfolio status, including scope, milestones, dependencies, risks, resourcing, and decision needs
- Establish and manage portfolio reporting for the Chief Transformation Officer, executive leadership, and the Board
- Lead high-priority, high-impact cross-functional initiatives from planning through execution
- Identify and address scope, schedule, dependency, and resourcing risks
- Unblock cross-functional issues and hold initiative owners and functional leaders accountable
- Coordinate with Change Management, Communications, and Value & Data teams on adoption, messaging, business cases, and value tracking
- Prepare analysis, recommendations, and decision support for portfolio reviews and steering discussions
- Communicate complex, technical, and ambiguous topics to executive leaders, stakeholders, and working teams
- Build alignment across stakeholders with different priorities and levels of transformation involvement
- Improve transformation delivery practices, operating rhythms, and cross-functional coordination
Requirements:
- 5+ years of experience in operations, program management, project management, management consulting, transformation, or a related field
- Bachelor's degree required
- Proven experience leading large, complex, cross-functional programs across multiple workstreams and stakeholder groups
- Experience leading a PMO, program delivery function, or enterprise governance model preferred
- Experience supporting or partnering with a Chief Transformation Officer, executive transformation leader, or similar executive sponsor strongly preferred
- Ability to translate strategic priorities into structured plans, delivery roadmaps, sequencing recommendations, and execution rhythms
- Strong understanding of delivery governance, RAID management, stage-gates, portfolio reporting, dependency tracking, and executive-level decision support
- Experience coordinating organizational change and supporting adoption of new processes, systems, or ways of working across functions
- Track record of partnering on value realization, business case tracking, or benefit measurement
- Ability to make confident, fact-based decisions and develop practical recommendations in ambiguous or limited-data environments
- Strong analytical, structured problem-solving, and critical-thinking skills
- Excellent written, verbal, and executive communication skills
- Strong relationship-building and influencing skills across executives, functional leaders, initiative owners, and front-line teams
- High ownership mindset with ability to drive accountability, manage competing priorities, and deliver results in a fast-moving environment
- Insurance industry experience preferred
Benefits:
- Comprehensive health and welfare program for employees, family members and domestic partners
- Medical, Dental, and Vision Benefits
- Flexible Spending Account (FSA)
- Health Savings Account (HSA)
- Commuter Transit Programs
- Company paid Short-Term Disability
- Company paid Long-Term Disability
- Company paid Group Term Life
- Company paid Employee Assistance Program
- Paid Parental Leave
- Paid holidays
- Personalized PTO
- 401(k) with employer match
- Flexible and collaborative environment
- Enhanced career opportunities
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