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

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 an Engagement Manager at Skylight, the current salary ranges are as follows:

• Associate Engagement Manager: $90,000–$125,000
• Engagement Manager I: $120,000–$140,000
• Engagement Manager II: $135,000–$160,000
• Senior Engagement Manager: $150,000–$185,000
• Staff Engagement Manager: $170,000–$203,000
• Principal Engagement Manager: $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 $2000 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)
• Flexible, remote-friendly work environment
• An environment that empowers you to unleash your superpowers for public good

Interview tips

Our process includes a preliminary screen, a skills interview, a behavioral interview, and a reverse interview where you meet your potential team — usually four conversations across two to three weeks. 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.
• Browse our case studies to learn more about our work.

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.