Deputy Director of Strategy

DescriptionMassHealth 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.Duties and Responsibilities: (These duties are a general summary and not all-inclusive)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.Preferred Qualifications: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.Proficiency with Microsoft Office Suite, particularly Word, Excel, and Outlook.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.To Apply:Please upload both Resume and Cover Letter for this position when applying. First consideration will be given to those applicants that apply within the first 14 days.About MassHealth:MassHealth is the Commonwealth's Medicaid and Children's Health Insurance Program, providing comprehensive healthcare coverage and services to approximately two million Massachusetts residents. Through partnerships with providers, health plans, community organizations, and government agencies, MassHealth works to improve health outcomes, reduce disparities, strengthen care coordination, and ensure access to high-quality, person-centered care. As one of the largest Medicaid programs in the country, MassHealth plays a critical role in advancing healthcare innovation, promoting health equity, and supporting the well-being of individuals, families, and communities across the Commonwealth. Learn more: MassHealthPre-Offer Process:A criminal and tax history background check will be completed on the recommended candidate as required by the regulations set forth by the Executive Office of Health and Human Services prior to the candidate being hired. For more information, please visit Education, licensure and certifications will be verified in accordance with the Human Resources Division’s Hiring Guidelines.Education and license/certification information provided by the selected candidate(s) is subject to the Massachusetts Public Records Law and may be published on the Commonwealth’s website.If you require assistance with the application/interview process and would like to request an ADA accommodation, please click on the link and complete the ADA Reasonable Accommodation Request Form.For questions, please the contact the Office of Human Resources at View phone number on us.fitly.work and select option #4.QualificationsMINIMUM ENTRANCE 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.Substitutions:I. A certificate in a relevant or related field may be substituted for one (1) year of the required (A) experience.II. A Bachelor's degree in a related field may be substituted for two (2) years of the required (A) experience.III. A Graduate degree in a related field may be substituted for three (3) years of the required (A) experience.IV. A Doctorate degree in a related field may be substituted for four (4) years of the required (A) experience.Salary placement is determined by a combination of factors, including the candidate’s years of directly related experience and education, and alignment with our internal compensation structure as set forth by the Human Resources Division’s Hiring Guidelines. For all bargaining unit positions (non-management), compensation is subject to the salary provisions outlined in the applicable collective bargaining agreement and will apply to placement within the appropriate salary range.Comprehensive BenefitsWhen you embark on a career with the Commonwealth, you are offered an outstanding suite of employee benefits that add to the overall value of your compensation package. We take pride in providing a work experience that supports you, your loved ones, and your future.Want the specifics? Explore our Employee Benefits and Rewards!An Equal Opportunity / Affirmative Action Employer. Females, minorities, veterans, and persons with disabilities are strongly encouraged to apply.The Commonwealth is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, sex, gender identity or expression, sexual orientation, age, disability, national origin, veteran status, or any other basis covered by appropriate law. Research suggests that qualified women, Black, Indigenous, and Persons of Color (BIPOC) may self-select out of opportunities if they don't meet 100% of the job requirements. We encourage individuals who believe they have the skills necessary to thrive to apply for this role.Job Field: Administrative ServicesOrganization: Exec Office Of Health and Human ServicesSchedule: Full-timeShift: Day