Deputy Director of Strategy

Commonwealth of Massachusetts • Boston, MA

1d

About The Position

MassHealth is seeking an experienced and strategic leader to serve as Deputy Director of Strategy, an important leadership role focused on some of the agency’s most complex and consequential priorities. As the Commonwealth’s Medicaid and Children’s Health Insurance Program, MassHealth provides health care coverage and related services to approximately two million Massachusetts residents. The Deputy Director will work closely with the Director of Strategy, Medicaid Director, MassHealth executive team, and leaders across the agency to shape strategies that strengthen health care access, quality, member experience, and the long-term sustainability of the program. This position offers a unique opportunity to help address challenging issues at the intersection of health policy, finance, operations, data, and technology while contributing to decisions that directly affect members, providers, and communities across Massachusetts.
As a senior leader on the MassHealth Strategy team, the Deputy Director will lead complex initiatives from early problem-solving and strategy development through recommendations or implementation, bringing together diverse perspectives and translating analysis into practical recommendations and action. The selected candidate will also lead and develop members of the Strategy team, advise senior executives, and help strengthen how MassHealth approaches emerging challenges and opportunities. This role is especially well suited for someone who enjoys solving difficult problems, working across organizational boundaries, developing others, and turning complex information into clear direction. It provides significant exposure to senior leadership and an opportunity to grow as a strategist and people leader while contributing to the future of one of the Commonwealth’s largest and most important public programs.

Requirements

• Applicants must have at least (A) five (5) years of full-time or, equivalent part-time, professional, administrative, supervisory, or managerial experience in business administration, business management, public administration, public management, clinical administration or clinical management of which (B) at least one (1) year must have been in a project management, supervisory or managerial capacity or (C) any equivalent combination of the required experience and substitutions below.
• Proficiency with Microsoft Office Suite, particularly Word, Excel, and Outlook.

Nice To Haves

• Demonstrated success leading complex, cross-functional strategic initiatives from problem definition and analysis through executive recommendation and implementation.
• Skilled in structured problem-solving, including defining key questions, developing analytical approaches, evaluating alternatives, and translating complex information into practical recommendations.
• Diverse backgrounds welcome, including management consulting, private sector strategy, health care strategy, performance improvement, public-sector strategy, or other highly analytical and project-based environments.
• Proven ability to analyze financial, operational, health care, or other complex data and use quantitative and qualitative findings to support strategic decisions.
• Demonstrated experience developing financial models, business cases, scenario analyses, or other decision-support tools for senior leaders.
• Excellent written, verbal, presentation, and executive communication skills, with the ability to make complex issues understandable and actionable for varied audiences.
• Track record of leading, coaching, and developing staff while establishing clear expectations and maintaining high standards for analytical quality, communication, and execution.
• Adept at building trusted relationships, navigating differing perspectives, and influencing decisions across organizational boundaries without relying on formal authority.
• Demonstrated capacity to manage multiple priorities, exercise sound judgment in rapidly changing circumstances, and deliver high-quality work within demanding timelines.
• Strong understanding of health care policy, financing, operations, or delivery, with knowledge of Medicaid, health care payment reform, value-based care, or federal health policy particularly beneficial, but not required.

Responsibilities

• Lead a portfolio of high-priority strategic, policy, operational, and implementation initiatives from initial problem definition through execution.
• Translate complex and often ambiguous challenges into clear questions, hypotheses, workstreams, analytical approaches, decision points, and actionable plans.
• Assemble and lead cross-functional teams across program, policy, finance, legal, clinical, operations, data, and technology functions to advance shared priorities.
• Establish effective project governance, roles, timelines, milestones, and accountability to support successful execution of complex initiatives.
• Direct qualitative and quantitative analyses using medical claims, financial information, operational performance data, benchmarks, trends, and stakeholder input to evaluate opportunities and inform decisions.
• Develop financial and operational models, scenario analyses, business cases, and other decision-support tools to assess strategic options and potential impacts.
• Synthesize policy, financial, operational, analytical, and stakeholder considerations into practical options and clear recommendations for senior leadership.
• Prepare and present executive-level briefings, analyses, recommendations, and decision materials for the MassHealth executive team, Medicaid Director, and other senior Commonwealth leaders.
• Manage, coach, and develop Senior Managers, Program Managers, and other team members by assigning work, providing feedback, strengthening analytical and communication skills, and supporting professional growth.
• Engage members, advocates, providers, vendors, federal partners, state agencies, and other stakeholders to gather perspectives, build alignment, and strengthen strategies and implementation plans.
• Partner with the Director of Strategy to shape the team’s project portfolio, strengthen strategic planning, improve team tools and methods, and identify opportunities to increase the Strategy team’s impact across MassHealth.
• Advance emerging agency priorities by responding to legislative, regulatory, executive, and operational needs and helping leadership translate urgent challenges into coordinated action.

Benefits

• Comprehensive Benefits
• outstanding suite of employee benefits that add to the overall value of your compensation package
• work experience that supports you, your loved ones, and your future

What This Job Offers

• Job Type: Full-time
• Career Level: Manager