Principal Digital Acquisition Consultant (CMS)

Skylight

1d•$180,000 - $230,000•Remote

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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

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