Director of Strategic Initiatives (Remote)

Patriot Growth Insurance Services and Partner Agencies•Fort Washington, PA

2d•Remote

About The Position

Patriot Growth Insurance Services is a rapidly growing national insurance services firm founded in 2019, partnering with employee benefits and property and casualty agencies. Ranked as the 25th largest broker in the U.S. and named to the Inc. 5000 list, Patriot has over 2,100 employees across 150+ locations in 45 states. The company offers a collaborative model providing resources and strategic support to its agencies, fostering career growth and operational excellence. This role is crucial for supporting enterprise transformation by strengthening delivery discipline and ensuring strategic initiatives are executed with clarity, accountability, and measurable business impact.

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.
Demonstrated 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 for strategic, operational, or technology initiatives.
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, with the ability to simplify complex topics for different audiences.
Strong relationship-building and influencing skills with the ability to work effectively across executives, functional leaders, initiative owners, and front-line teams.
High ownership mindset with the ability to drive accountability, manage competing priorities, and deliver results in a fast-moving environment.

Nice To Haves

MBA preferred.
Insurance industry experience preferred.

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 business 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 consistent 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 the portfolio reporting rhythm for the Chief Transformation Officer, executive leadership, and the Board.
Personally lead a focused set of high-priority, high-impact cross-functional initiatives from planning through execution.
Identify scope, schedule, dependency, and resourcing risks early, and take action to prevent downstream impact.
Unblock issues that cross functional or team boundaries while holding initiative owners and functional leaders accountable to commitments.
Coordinate with Change Management, Communications, and Value & Data teams to ensure adoption, messaging, business cases, and value tracking are aligned with initiative delivery.
Partner with the Chief Transformation Officer to prepare analysis, recommendations, and decision support for portfolio reviews and steering discussions.
Communicate complex, technical, and ambiguous topics clearly to executive leaders, functional stakeholders, and working teams.
Build alignment across stakeholders with different priorities, working styles, and levels of transformation involvement.
Support continuous improvement of transformation delivery practices, operating rhythms, and cross-functional coordination.