Enterprise Strategy & Initiatives Director

Delta Dental of Massachusetts; Boston (MA); On-site; USD 162,000 - 191,000; Full time

Benefits offered by this job

Medical, dental, and vision plans

Generous PTO (paid time off)

Disability insurance

401(k) match with financial planning

Job summary

Delta Dental of Massachusetts seeks a Director, Strategic Initiatives to lead the organization’s strategic planning process and oversee enterprise-wide initiatives that accelerate growth, operational excellence, and long-term objectives.

The role will manage a team of project managers and coordinate transformation programs with executive leadership to translate strategy into actionable roadmaps and measurable outcomes.

Qualifications

• 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Skills

Strategic planning

Program management

Leadership

Executive communication

Financial analysis

Stakeholder management

Change management

Education

Bachelor's degree in Business Administration, Healthcare Management, Project Management, Finance, Operations, or related field

Master's degree (preferred)

Tools

Microsoft Office

Job description

Delta Dental of Massachusetts seeks a Director, Strategic Initiatives to lead the organization’s strategic planning process and oversee enterprise-wide initiatives that accelerate growth, operational excellence, and long-term objectives.

The role will manage a team of project managers and coordinate transformation programs with executive leadership to translate strategy into actionable roadmaps and measurable outcomes.