Director of Strategic Initiatives

🕒 Yesterday

🔔 Pennsylvania, Washington – Remote

🔔 Pennsylvania – Remote ☕ Washington – Remote

💵 $200k - $250k / year

⏰ Full Time

🔴 Lead

🧐 Strategy

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Patriot Growth Insurance Services, LLC

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2019

🛡️ Insurance

💸 Finance

🤝 B2B

💰 Debt Financing on 2022-08

Insurance • Finance • B2B

Patriot Growth Insurance Services, LLC is a leading provider of risk management and insurance solutions that focuses on promoting business growth and safeguarding personal goals. With a commitment to delivering unparalleled service, they empower local brokers to offer comprehensive insurance options tailored to meet the diverse needs of businesses and individuals. By leveraging an expansive network of national carrier partners, they specialize in property & casualty and employee benefits, ensuring their clients receive the protection and support necessary to confidently pursue their goals.

📋 Description

• 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