Director, Strategic Initiatives

Job Summary

The Director, Strategic Initiatives is responsible for leading the organization's strategic planning process and overseeing the execution of enterprise-wide initiatives that drive business growth, operational excellence, and long-term organizational objectives. This role serves as a key partner to executive leadership in translating strategy into actionable plans, measurable outcomes, and sustainable operational improvements.

The Director will lead a portfolio of strategic and operational initiatives from concept development through implementation and benefits realization. This role manages a team of Project Managers and provides oversight of both transformational initiatives and steady-state operational programs. Success requires exceptional strategic thinking, executive presence, project and portfolio management expertise, financial acumen, organizational influence, and the ability to align cross-functional stakeholders around shared business priorities.

The Director will work closely with leaders across the enterprise and external partners to ensure strategic priorities are effectively planned, prioritized, executed, and sustained.

Primary Responsibilities

Strategic Planning & Enterprise Alignment

• Lead the annual and multi-year strategic planning process in partnership with the executive leadership team.
• Facilitate strategic planning sessions, organizational goal setting, and enterprise prioritization activities.
• Translate organizational strategy into actionable roadmaps, initiatives, milestones, and measurable outcomes.
• Develop and maintain executive-level strategic plans, dashboards, and performance metrics.
• Monitor industry, competitive, operational, and organizational trends to identify strategic opportunities and risks.
• Support executive leadership with strategic analyses, recommendations, and decision support materials.

Enterprise Initiative & Portfolio Leadership

• Lead a portfolio of enterprise-wide initiatives and operational improvement efforts aligned with organizational priorities.
• Establish governance structures, steering committees, operating mechanisms, and decision-making frameworks.
• Evaluate new initiatives and project requests, assess organizational impact, and recommend prioritization approaches.
• Ensure alignment of initiatives with strategic objectives, resource capacity, budget expectations, and business outcomes.
• Drive accountability for initiative execution, milestone achievement, and benefits realization across departments.
• Serve as escalation point for complex initiatives, organizational barriers, resource conflicts, and cross-functional issues.

Program & Project Management Oversight

• Provide leadership and oversight for multiple concurrent strategic and operational projects.
• Establish and maintain project management methodologies, tools, reporting standards, and governance practices.
• Oversee project scope, timelines, budgets, risks, dependencies, and resource planning.
• Standardize portfolio reporting, executive status updates, KPI tracking, and risk management practices.
• Drive continuous improvement within project management processes and organizational delivery capabilities.
• Ensure successful transition of initiatives into business operations and steady-state support models.

Team Leadership & Development

• Directly manage and develop a team of Project Managers responsible for enterprise initiatives and operational projects.
• Establish performance expectations, development plans, and coaching strategies to build project management capabilities.
• Mentor team members in project management methodologies, stakeholder management, executive communications, and leadership skills.
• Manage team workload, resource allocation, and project assignments to ensure effective delivery.
• Foster a culture of accountability, collaboration, continuous improvement, and strategic thinking.

Financial & Business Analysis

• Develop and review business cases, financial models, cost-benefit analyses, and return-on-investment assessments.
• Partner with Finance to build initiative budgets, monitor financial performance, and track realization of expected benefits.
• Evaluate strategic opportunities through quantitative and qualitative analysis.
• Support annual operating planning and long-range planning activities.
• Measure and communicate the financial and operational impact of strategic initiatives.

Executive Communications & Stakeholder Management

• Develop executive-ready presentations, reports, and recommendations for senior leadership and Board-level discussions.
• Facilitate discussions among senior leaders to drive alignment, decision-making, and organizational accountability.
• Communicate project status, risks, dependencies, and recommendations clearly and proactively.
• Build strong relationships across departments and effectively influence without direct authority.
• Lead organizational communications related to major initiatives, strategic priorities, and operational changes.

Change Management & Operational Readiness

• Partner with business leaders to ensure successful adoption of new processes, systems, and operating models.
• Lead change management planning, readiness assessments, communication strategies, and adoption efforts.
• Coordinate operational readiness activities, training plans, and transition planning.
• Monitor post-implementation performance and ensure sustainability of initiative outcomes.
• Identify opportunities to improve organizational effectiveness, operating models, and cross-functional collaboration.

Job Qualifications

Required

• Bachelor's degree in Business Administration, Healthcare Management, Project Management, Finance, Operations, or related field.
• 10+ years of progressive experience in strategic planning, enterprise project management, business operations, management consulting, PMO leadership, or corporate strategy.
• 5+ years leading large-scale cross-functional initiatives with enterprise-wide impact.
• 3+ years of people leadership experience, including management and development of project managers or professional staff.
• Demonstrated experience facilitating strategic planning and organizational prioritization processes.
• Strong business and financial acumen with experience developing business cases and investment analyses.
• Expertise in project, program, and portfolio management methodologies.
• Outstanding communication, facilitation, stakeholder management, and executive presentation skills.
• Proven ability to influence senior leaders and drive alignment across diverse stakeholder groups.
• Advanced proficiency in Microsoft Office applications, project management tools, reporting platforms, and presentation development.

Preferred

• Master's degree in Business Administration, Healthcare Administration, Project Management, or related field.
• PMP certification or equivalent project management certification.
• Experience in healthcare, dental benefits, insurance, payer organizations, or regulated industries.
• Experience leading organizational transformations, operating model redesigns, or enterprise strategic initiatives.
• Experience with portfolio management, strategic planning frameworks, OKRs, or balanced scorecard methodologies.
• Knowledge of business intelligence platforms.

The target hiring range for this role is $161,925- $190,500 (Annually). The starting base salary will be determined based on skills, experience, and other job-related factors. In addition, our total rewards package includes medical, dental, and vision plans; generous time off including PTO, short and long-term disability insurance and a competitive 401(k) savings match including financial planning workshops. See our Careers Page for more information.

The specific statements shown in each section of this description are not intended to be all-inclusive. They represent typical elements and criteria necessary to successfully perform this position.

In accordance with Delta Dental of Massachusetts’ Compliance Plan, all employees must conduct Delta Dental of Massachusetts business and activities in accordance with applicable laws, regulations, professional standards, and ethical standards and report potential compliance or ethical issues to Delta Dental of Massachusetts’ designated Compliance Officer.

Delta Dental of Massachusetts’ Affirmative Action Program affirms our commitment to make reasonable accommodations for known physical or mental limitations of otherwise qualified individuals with disabilities or special disabled veterans unless the accommodation would impose an undue hardship on the operation of our business and activities. Please see Human Resources for additional information regarding this program.