Director of Strategic Initiatives
Director of Strategic Initiatives
Why This Role Matters
How You'll Make an Impact
- 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.
Who You Are
- A strategic operator who thrives at the intersection of planning, execution, and organizational transformation.
- Skilled at bringing structure, clarity, and momentum to complex and ambiguous environments.
- Comfortable influencing executives, functional leaders, and project teams without relying solely on formal authority.
- Highly organized and able to balance competing priorities while maintaining focus on long-term business objectives.
- A proactive problem solver who anticipates challenges, removes obstacles, and drives accountability across stakeholders.
- An exceptional communicator who can distill complex topics into clear recommendations and actionable next steps.
- Results-oriented, collaborative, and committed to delivering meaningful business value through transformation initiatives.
What You Bring
Day One:
- 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.
Valuable Additions:
- 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.
Real Benefits for Real Life
- 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 to help you navigate benefits, compare prescription costs, and make more confident, personalized care decisions
- 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
About Patriot Growth Insurance Services
Pay Range: Posted below*
*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. There is no guarantee an offer will be at the top of the posted range based on the salary analysis. Roles may also be eligible for a supplemental compensation, such as performance-based bonus, commission, or equity. Specific eligibility will be discussed with Talent Acquisition team.
Patriot Growth Insurance Services offers a comprehensive benefits package, including medical, dental, and vision insurance; a 401(k) with company match; personalized time off and company paid holidays.
Pay Range
$200,000 - $250,000 USD
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