Staff/Principal Engagement Manager (CMS)

Skylight

1d•$170,000 - $230,000•Remote

About The Position

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.

Requirements

Demonstrated experience leading end-to-end delivery of complex projects or programs, preferably in a product management, delivery, or consulting capacity
Strong ability to turn ambiguous, evolving requirements into clear plans, priorities, and actionable work for teams and stakeholders
Experience working at the intersection of policy, operations, and technology, with the ability to translate between non-technical and technical audiences
Ability to manage multiple concurrent workstreams or client engagements while maintaining high-quality, outcome-driven delivery
Experience coordinating across multiple stakeholders, including senior leaders, and building alignment in complex, multi-layered environments
Familiarity with agile and iterative delivery approaches (for example, Scrum or Kanban), and the ability to apply them pragmatically in real-world settings
Ability to identify and remove blockers across policy, operational, and technical domains to keep teams moving forward
Strong systems thinking skills, with the ability to understand how policies, processes, technology, and data interact within large organizations
Comfort working with technical systems, data flows, and legacy environments, with enough fluency to collaborate effectively with engineering and data teams
Experience working in or with government, healthcare, or other highly regulated environments, or the ability to quickly navigate complex regulatory contexts
Ability to build trusted relationships with clients and partners, and communicate effectively in a professional services environment
Ability to provide clear visibility into delivery status, risks, and outcomes to a range of stakeholders
Commitment to continuous improvement, including facilitating retrospectives and applying learnings to improve team performance and outcomes
Ability to work successfully within a professional services environment (e.g., can communicate effectively with clients)
Passion for improving public outcomes through great government services
A mindset and work approach that align with Skylight’s core values
Ability to travel for work from time to time
All work must be conducted within the U.S., excluding U.S. territories. Some federal contracts require U.S. citizenship to be eligible for employment.
You must be legally authorized to work in the U.S. now and in the future without sponsorship.
As a government contractor, you may be required to obtain a public trust or security clearance.
You may be required to complete a company background check successfully.
Some of our available roles are on federal contracts that require a degree or additional years of experience as a substitute.

Nice To Haves

Experience collaborating with state government partners
Experience with Medicaid, SNAP or other public benefit programs
Experience in civic tech, government, or other highly regulated environments
Experience working in a remote-team environment

Responsibilities

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 implement improvement actions
Provide management- and team-level visibility into the status and health of the engagement and serve as primary coordinator for budget, travel, and other administrative requirements

Benefits

Medical insurance, dental insurance, vision insurance
Short-term and long-term disability insurance
Life and AD&D insurance
Dependent care FSA, healthcare FSA, health savings account
Dollar-for-dollar 401(k) match up to 10% of your salary with no vesting period
Flexible paid time-off-policy (generally around 25 days per year), plus 11 paid federal holidays
Up to 12 weeks paid-time-off for all eligible new birth, adoption, or foster parents
Performance rewards, including annual salary increase, annual performance bonus, spot bonuses, and stock options
Business development / sales bonuses
Referral bonuses
Annual $2,000 allowance for professional development
Annual $750 allowance for tech-related purchases
Annual swag budget of $100 to display your Skylight pride with some merchandise (hoodies, hats, and more)
Dollar-for-dollar charity donation matching, up to $500 per year
Flexible, remote-friendly work environment
An environment that empowers you to unleash your superpowers for public good