Senior/Staff/Principal Digital Acquisition Consultant (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

As a Digital Acquisition Consultant, you’ll partner with state Medicaid agencies and CMS to transform how government buys the technology that powers public benefits. This is a high-stakes, delivery-oriented role focused on helping states navigate the "policy-tech boundary" to implement new federal requirements.

You won't just be drafting paperwork; you'll be a strategic advisor translating complex statutory requirements into clear operational needs. You’ll help states move away from prescriptive, task-based contracting toward outcome-oriented strategies that ensure eligible people maintain their coverage. Operating across multiple states under tight deadlines, you’ll use modern procurement playbooks and agile methods to help agencies build, buy, and ship the right technical solutions.

What you’ll do

• Translate statutory requirements into clear operational needs for state Medicaid, IT, and procurement staff
• Analyze existing state eligibility systems and landscape gaps to guide states on whether to build, buy, configure, or leverage shared services like open-source options or CMS tools
• Coach states to shift from prescriptive Statements of Work (SOWs) toward Statements of Objectives (SOOs) focused on measurable results and human-centered outcomes
• Create criteria to evaluate vendor delivery capability and structure pricing for phased, iterative delivery that aligns with federal milestones
• Adapt procurement playbooks to fit specific state regulatory environments by creating reusable templates for SOO language, evaluation rubrics, and decision frameworks
• Perform "red-team" reviews of draft solicitations to identify risks like vendor lock-in, weak acceptance criteria, or missing exit provisions before they are released
• Apply agile methods at the intersection of policy and technology to help states maintain flexibility for evolving federal guidance while moving quickly against strict timelines

What we're looking for

Minimum qualifications

• Experience in government procurement, acquisitions, or contract management, specifically for digital services or complex IT systems
• Proven ability to translate policy or statutory requirements into technical and operational specifications
• Experience working in highly regulated, delivery-oriented, or project-based environments
• Strong understanding of modern technology procurement, including "Build vs. Buy" frameworks and outcome-based contracting
• Experience guiding cross-functional teams and holding delivery accountability through launch
• Track record of owning a procurement, product, or program implementation strategy end-to-end across multiple stakeholders, including navigating competing priorities to keep things moving
• Ability to work successfully within a professional services environment (e.g., can communicate effectively with clients)
• Passionate about creating better public outcomes through great government services
• A mindset and work approach that aligns with our core values
• Ability to travel for work from time to time

Nice-to-have qualifications

• Experience collaborating with state government partners
• Experience with Medicaid, Medicare, or healthcare programs
• Experience making procurement processes work better — mapping how things actually flow, finding what's broken, and fixing it
• Understanding of how modern tech teams are structured and collaborate
• Experience working in a remote-team environment.
• Prior experience working in the civic tech procurement space
• Experience working in a remote-team environment
• Digital IT Acquisition Program (DITAP) Graduate

Don’t meet every qualification but think you can do the job? We’d still love to hear from you. If you’re excited about the role, apply. We consider candidates with a range of backgrounds and experiences.

Other requirements

• 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