Senior IT Project Manager

The Executive Office of Technology Services and Security (EOTSS) is the lead enterprise technology organization for the Commonwealth of Massachusetts. Charged with driving the ongoing alignment of business and technology across the Commonwealth’s Executive Branch, EOTSS oversees and manages the enterprise technology, digital infrastructure and services, as well as the Commonwealth Security Operations Center and an enterprise Standard Operating Environment that includes an information security and risk management framework for over 125 state agencies and over 43,000 state employees. We directly serve our constituents by providing digital services and tools that enable taxpayers, drivers, businesses, visitors, families and other citizens to do business with the Commonwealth in a way that makes every interaction with government easier, faster, and more secure.

Our Mission: We provide technology leadership across the Commonwealth to enhance the quality of public service and foster positive community outcomes.

The Opportunity:

EOTSS is seeking a highly adaptable Senior IT Project Manager to support a range of complex, high-impact technology initiatives.

This is not a traditional project management role. We are looking for a strategic operator – someone who can step into evolving, ambiguous environments and quickly bring structure, alignment, and forward momentum. You will be deployed across initiatives based on organizational need, often working with large, cross-functional stakeholder groups and shifting priorities.

The ideal candidate thrives in complexity, leads through change, and is equally comfortable shaping a problem as they are executing against it.

This role is ideal for a project leader who:

• Enjoys being dropped into complex situations and figuring things out
• Thrives in fast-moving, evolving environments
• Wants exposure to a wide range of high-impact initiatives
• Is motivated by driving real change—not just managing timelines

The work location for this role will be alternating between two EOTSS office locations:

• One Ashburton Place, Boston, Massachusetts 02108
• 200 Arlington Street, Chelsea, Massachusetts 02150

The work schedule for this position is Monday through Friday, 9:00AM – 5:00PM EST. This position is expected to follow a hybrid model of reporting to work that combines in-office workdays and work from home days as needed. Occasional local travel may be required.

All offers of employment into this position are conditional and subject to passing: a Massachusetts Criminal Background Check (CORI); a security clearance (fingerprinting) consistent with IRS and/or public safety requirements; and security training.

Position Responsibilities (including but not limited to):

Lead Complex, Cross-Functional Initiatives

• Drive delivery of large-scale, high-visibility IT initiatives aligned to Commonwealth priorities
• Quickly ramp up on new projects, domains, and stakeholder environments with minimal onboarding
• Bring structure and clarity to ambiguous or evolving initiatives
• Own outcomes, not just execution

Operate Effectively in Dynamic Environments

• Manage multiple initiatives or transition between projects as priorities shift
• Define scope, governance, and delivery approach in environments where processes may not yet be established
• Maintain progress and alignment despite changing requirements and competing demands

Drive Organizational Change

• Lead change management efforts across people, process, and technology
• Develop and execute stakeholder engagement, communication, and adoption strategies
• Identify and mitigate resistance, ensuring successful implementation and sustained outcomes

Navigate Complex Stakeholder Ecosystems

• Build alignment across diverse stakeholders including executive leadership, technical teams, vendors, and business partners
• Influence without direct authority in a highly matrixed organization
• Manage competing priorities and facilitate decision-making across groups with differing perspectives

Shape and Deliver Solutions

• Translate loosely defined ideas or business needs into structured plans and actionable deliverables
• Partner with leadership to define success metrics, scope, and execution strategy
• Ensure technical and business alignment while advocating for effective, pragmatic solutions

Drive Execution and Transparency

• Develop and maintain project artifacts including plans, timelines, budgets, and executive communications
• Deliver clear, concise status reporting and presentations to leadership
• Identify risks, manage dependencies, and proactively resolve issues

Continuously Improve Delivery

• Conduct post-implementation reviews to capture lessons learned
• Contribute to the evolution of PMO processes, tools, and standards
• Support broader strategy and planning efforts across the portfolio

What Success Looks Like

• Quickly establishes clarity and direction in complex or underdefined initiatives
• Builds trust and alignment across large, diverse stakeholder groups
• Drives measurable progress despite ambiguity and shifting priorities
• Successfully enables adoption of new systems, processes, or operating models
• Steps into challenging situations—including at-risk projects—and stabilizes delivery

Required Knowledge, Skills and Experience:

• 5–7 years leading complex, enterprise-scale IT projects or programs within large, matrixed organizations
• Demonstrated track record delivering initiatives that drive significant organizational, operational, or technology transformation
• Proven ability to lead effectively in ambiguous, fast-paced environments, bringing clarity, structure, and forward momentum
• Strong stakeholder leadership skills, with a track record of influencing senior executives and aligning cross-functional teams
• Experience driving end-to-end change management, including stakeholder alignment, communication strategies, and adoption outcomes
• Ability to rapidly assess complex situations, identify gaps, and implement scalable processes and governance
• Exceptional communication skills, with experience delivering executive-level presentations and concise written reporting
• Deep knowledge of project management methodologies (Agile, Waterfall, hybrid) and enterprise governance frameworks

Preferred Knowledge, Skills and Experience:

• Experience stabilizing or turning around at-risk or underperforming projects
• Strong understanding of IT infrastructure, cloud technologies, or enterprise systems
• Experience with business process mapping, process redesign, and workflow optimization
• Familiarity with tools such as Microsoft Project, JIRA, SPM, or similar platforms
• PMP, PM-ACP, CSM, or equivalent certification
• Experience in government or public-sector environments