Staff/Principal Engagement Manager (U.S. Air Force)

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 agile project management practices, agile coaching at the organizational and team levels, project status and progress reporting, risk/issue management, stakeholder management, continual improvement, and contract administration in order to deliver the highest levels of client service and work.

Skylight has partnered with the U.S. Air Force across multiple legacy modernization efforts. The work spans modernization of legacy systems, new capability development in multi-vendor environments, iteration on established platforms, all inside an agile transformation and broader organizational change.

You’ll lead this engagement end to end: owning the client relationship, keeping delivery on track across several teams and vendors, and shaping how Skylight grows the account. It’s a highly complex and consultative environment, so you’ll spend as much time aligning stakeholders and enabling your government partners as you do managing the work.

What to know going in

Your first 30 days are about working with the Skylight team and government personnel, learning the client’s domain and organization, and enabling your government partners. Access to users varies from team to team, so you’ll need to get creative about how you reach them. The client is early- to mid-transformation, so expect organizational and operational change along the way.

This role is contingent on Skylight being awarded the underlying contract. If we’re not awarded the contract, we’ll let you know promptly and discuss whether there are other opportunities that fit.

What you’ll do

• Translate the client’s objectives and constraints into an engagement approach that’ll deliver a unique experience and impactful results in the shortest amount of time possible
• Build trust with a wide range of stakeholders across the client organization, partner vendors, and Skylight, and keep them aligned on priorities and progress
• Manage multiple projects aimed at delivering transformation or a specific product using the appropriate methodologies (e.g., Scrum or kanban)
• 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
• Identify opportunities to expand Skylight’s work with the client, and help shape proposals, renewals, and account strategy
• Provide management- and team-level visibility into the status and health of the engagement

What we’re looking for

• Basic qualifications
• Understand how to apply agile principles to project and program management
• Ability to understand client needs and build long-lasting, meaningful relationships with them
• Ability to grow Skylight’s business through business development activities
• Can cultivate team health, including establishing psychologically safe environments
• Can ensure that each project is staffed with the appropriate level and types of personnel
• Can ensure that teams are compliant with their contract’s terms and conditions
• Strong stakeholder management skills in complex, multi-vendor environments
• Interest in mentoring, coaching, and pairing with government partners so they can carry the work forward
• Experience working on cross-functional teams (product, design, engineering, ops) in iterative delivery
• A mindset and work approach that aligns with our core values
• Nice-to-haves
• Military or government experience
• Experience leading legacy modernization or agile transformation efforts
• Experience delivering technology in government, regulated industries, or other public-benefit settings
• A track record of staying aligned and accountable on remote teams
• 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
• Some of our available roles are on federal contracts that require a degree or additional years of experience as a substitute.
• All work must be conducted within the U.S., excluding U.S. territories.
• This contract requires U.S. citizenship to be eligible for employment.
• You must be able to obtain and maintain a Common Access Card (CAC), which requires a favorable background check.
• You must complete a company background check successfully.

Logistics

Position type

This is a full-time, exempt position.

Location

This is a fully remote position.

Travel

Expect occasional travel to Air Force bases across the U.S., quarterly at most.

Expected start date

November 2026

Care package