Senior/Staff Digital Transformer

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, digital transformers help government teams modernize how they buy, manage, and deliver technology at scale.

The U.S. Department of Health and Human Services (HHS) is launching one of the most ambitious transformations in government — and this is a rare chance to be part of it. You’ll join a high-impact team of product managers, researchers, designers, engineers, and security experts working side-by-side with HHS leadership to modernize the systems people rely on to access healthcare, strengthen cybersecurity that protects personal data, launch digital services used by tens of millions every day, and integrate data and AI responsibly into daily work across the department so teams at every level can make smarter, safer decisions.

As a digital transformer focused on procurement, you’ll apply modern acquisition practices — such as outcome-based requirements, modular contracting approaches, and performance-driven measures — to ensure HHS can buy and manage technology in ways that deliver real outcomes. Just as importantly, you’ll prepare federal teams to sustain these improvements by sharing knowledge and practices that last — from training and enablement to reusable tools like templates, playbooks, and decision records.

What you’ll do

• Advise on acquisition approaches that align with the Federal Acquisition Regulation (FAR) while enabling agile, modular delivery and user-centered outcomes
• Develop outcome-based requirements, evaluation methods, and performance measures — including Quality Assurance Surveillance Plans (QASP)
• Conduct vendor-neutral market research and analyses to inform government decision-making, highlighting options, tradeoffs, and risks
• Embed compliance needs into acquisition artifacts — including Section 508 of the Rehabilitation Act, the Federal Risk and Authorization Management Program (FedRAMP), privacy, and supply-chain requirements
• Help federal teams sustain improvements by delivering training and enablement, and by leaving behind reusable resources such as templates, playbooks, and decision records

What we're looking for

Minimum qualifications

• Knowledge of FAR and experience applying it to digital services or platforms
• Experience supporting complex technology acquisitions with outcome-based requirements, modular strategies, and performance measures
• Ability to translate technical goals into acquisition language that is fair, measurable, and testable — and to frame tradeoffs for decision-makers
• Familiarity with compliance requirements including Section 508, FedRAMP, privacy, and information security
• Strong communication and facilitation skills to build trust across contracting, legal, technical, and program stakeholders
• Commitment to equipping federal teams with documentation, training, and mentoring so improvements last beyond the contract
• Ability to work successfully in a professional services environment
• Passion for creating better public outcomes through great government services
• A mindset and work approach that align with Skylight’s core values

Nice-to-have qualifications

• Experience supporting acquisition modernization or category management in government or other regulated environments
• Background shaping solicitations for iterative delivery (e.g., modular contracting, performance-based acquisitions)
• Familiarity with enterprise software and cloud procurement patterns, including licensing optimization and shared services
• Experience in civic tech, government, or other highly regulated environments
• Experience working effectively on hybrid or distributed teams
• Ability to spend time on-site at HHS in Washington, DC — either by being based locally or by traveling periodically for in-person collaboration

Don’t meet 100% of the criteria but think you can do the job? We’d love to chat anyway! We’re on a mission to build diverse teams, and studies have shown that women and marginalized folks are less likely to apply to jobs if they don’t check every box.

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 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.

Position type

This is a full-time, exempt position.

Location

This is a remote-friendly role. You can be based anywhere in the U.S. Candidates in the Washington, DC area, or those willing to travel there periodically for in-person collaboration, are especially encouraged to apply.

Care package

Salary

We want to give you the most competitive salary possible. After all, you deserve it! To that end, we use the results of our interview process to determine what salary is most appropriate given your current level of seniority. For a Digital Transformer at Skylight, the current salary ranges are as follows:

• Associate Digital Transformer: $90,000–$125,000
• Digital Transformer I: $120,000–$140,000
• Digital Transformer II: $135,000–$160,000
• Senior Digital Transformer: $150,000–$185,000
• Staff Digital Transformer: $170,000–$203,000
• Principal Digital Transformer:  $180,000–$230,000

Benefits

Your well-being is important to us, so we focus on supporting you in a variety of ways:

• 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

Interview preparation

We want you to have a great interview experience with us! Here are some tips to help you prepare for a successful interview:

• Visit our join page to learn more about how our interview process works.
• Check out our Career Pathways framework to learn more about the different roles within Skylight and the skills needed to do them.
• If you’d like to request reasonable accommodations during the application or interviewing process, please contact our recruiting team at [email protected].

We participate in E-Verify and upon hire, will provide the federal government with your Form I-9 information to confirm that you’re authorized to work in the U.S.

We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, national origin, sex, religion, age, disability, veteran status, or any other category protected by applicable law.