Staff/Principal Engagement Manager (CMS)

About Skylight

Skylight is a digital consultancy using design and technology to help government agencies deliver better public services.

We’re at the forefront of a civic movement to reinvent how all levels of government serve families, patients, and many others in today's digital world.

If you want to play a part in driving this critical movement forward, we’d love for you to join our growing team of public interest technologists.

The work we do matters.

About the job

At Skylight, engagement managers are responsible for driving the overall success of our client work. They draw on their expertise in areas such as  product management practices, agile coaching at the organizational and team levels,, risk/issue management, stakeholder management, continual improvement, and contract administration in order to deliver the highest levels of client service and work.

In this role, you’ll lead the overall delivery of a team providing technical assistance to states as they implement Medicaid community engagement requirements under H.R. 1. You’ll be responsible for ensuring that states can translate federal policy into practical, state-specific solutions that work within their systems, constraints, and operational realities.

You’ll own the delivery and coordination of state engagements, serving as the central point of alignment across CMS, state partners, and internal multidisciplinary teams. This work sits at the intersection of policy and technology and requires navigating complex, multi-layered environments with many stakeholders and competing priorities.

This is a high-stakes, delivery-focused role where your ability to turn ambiguity into clarity is critical. You’ll translate evolving federal guidance into concrete plans, priorities, and execution pathways that teams can act on. You’ll guide teams through uncertainty, remove blockers, and ensure that work moves forward in a structured, outcome-driven way.

Operating at the policy to delivery boundary, you’ll coordinate across product, design, engineering, and operations to integrate new requirements into legacy systems, workflows, and data exchanges. Your leadership will ensure teams are not only compliant, but delivering high-quality, scalable solutions that improve how programs operate and how people experience them.

The work you do will directly shape how H.R. 1 is implemented across states, driving better outcomes by tailoring solutions to each state’s context while maintaining alignment with federal expectations.

What you’ll do

• Lead the end-to-end delivery of HR1 implementation engagements, ensuring states can translate federal Medicaid community engagement requirements into practical, state-specific solutions
• Turn ambiguous and evolving federal guidance into clear plans, priorities, and execution pathways that teams and state partners can act on
• Serve as the primary point of coordination across CMS, state agencies, and internal multidisciplinary teams, aligning complex senior federal and state stakeholder relationships, including navigating competing priorities, leadership styles, and politically sensitive environments to keep engagements moving forward
• Shape and execute engagement strategies that account for each state’s unique systems, constraints, and operational realities, balancing speed, quality, and compliance
• Assemble and lead multidisciplinary teams across product, design, engineering, and operations, including coordination with subcontractors where needed
• Manage multiple concurrent state engagements, using agile and delivery management practices (for example, Scrum or Kanban) to drive consistent, high-quality outcomes
• Proactively identify and remove delivery, policy, and technical blockers, enabling teams to move forward effectively in complex bureaucratic and legacy system environments
• Coach teams and partners on effective ways of working, fostering collaboration, ownership, and continuous improvement without over-prescribing process
• Facilitate structured feedback loops, including retrospectives with states, CMS, and internal teams, and translate insights into actionable improvements
• Provide clear, actionable visibility into delivery status, risks, and outcomes to stakeholders at all levels, from team members to senior federal and state leaders
• Assemble a multi-disciplinary team of experts from a variety of sources, including Skylight and other subcontractors, to deliver the engagement
• Set up the team for successful delivery by removing obstacles, coaching them on how to become more collaborative and self-organizing, and enabling the work they do rather than impose how it’s done
• Conduct retrospectives with both the client and Skylight team to learn what is and isn’t working well, and formulate and i