Director of Strategic Initiatives (Remote)

About Patriot Growth Insurance Services: Founded in 2019, Patriot is a growth-focused national insurance services firm that partners with employee benefits and property and casualty agencies across the United States. Patriot is currently ranked as the 25th largest broker in the U.S. by Business Insurance and has been named to the 2025 Inc. 5000 list of fastest-growing companies. With over 2,100 employees operating in 150+ locations in over 45 states, Patriot’s collaborative model delivers resources and strategic support to its agencies. Patriot creates true alignment with its partner agencies, and its operating philosophy fosters enhanced career opportunities for its dedicated and professional team. We are committed to working with like-minded individuals who share our vision of creating an insurance agency focused on operational excellence and a relentless pursuit of growth. Position Overview : We are seeking a strategic and execution-focused Director of Strategic Initiatives to partner closely with the Chief Transformation Officer and lead the delivery engine for the enterprise transformation portfolio. This role is responsible for owning the transformation PMO, driving delivery governance, personally leading high-priority cross-functional initiatives, and ensuring specialist functions are coordinated across the portfolio. The ideal candidate is a strong operator and program leader who can bring structure to ambiguity, influence stakeholders at all levels, and keep complex initiatives moving from strategy through execution. This position plays a key role in supporting enterprise transformation, strengthening delivery discipline, and ensuring strategic initiatives are executed with clarity, accountability, and measurable business impact. Work Arrangement: This is a full-time, fully remote position. Professional 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. Qualifications and Requirements: 5+ years of experience in operations, program management, project management, management consulting, transformation, or a related field. Bachelor’s degree required; MBA preferred. 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. Insurance industry experience preferred. Why Patriot Growth Insurance Services: We offer the opportunity to be a part of one of the fastest-growing insurance companies since its inception. We strive to create a flexible and collaborative environment for our employees, and our goal is to provide enhanced career opportunities for our dedicated and professional team. In addition to a competitive salary, we provide a comprehensive health and welfare program to employees, family members and domestic partners. Employees are eligible for benefits coverage the first of the month following 30 days of employment. We offer: Medical, Dental, and Vision Benefits Flexible Spending Account (FSA) and Health Savings Account (HSA) and Commuter Transit Programs Company paid Short-Term Disability, Long-Term Disability and Group Term Life Company paid Employee Assistance Program Paid Parental Leave Paid holidays Personalized PTO 401(k) with employer match Pay Range : $200,000 - $250,000 per year depending on experience. *A wide salary range is posted for this position and any job offer is based upon a salary analysis to comply with the required state pay transparency law. The salary analysis considers 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. Patriot Growth Insurance Services is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, citizenship or immigration status, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws. This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, leave of absence, compensation, benefits, and training. Patriot makes hiring decisions based solely on qualifications, merit, and business needs at the time. For more information, read through our EEO and DE&I Policy located on our website at www.patriotgis.com .