--- title: 'Senior/Staff/Principal Software Engineer, Legacy Modernization (U.S. Air Force) at Skylight' canonical: 'https://feeny.ai/job/senior-staff-principal-software-engineer-legacy-modernization-u-s-air-force-33js6fbv5aa4' type: 'job' last_seen: '2026-10-29' --- # Senior/Staff/Principal Software Engineer, Legacy Modernization (U.S. Air Force) at Skylight - **Company:** Skylight - **Location:** United States - **Posted:** 2026-10-24 - **Last confirmed live:** 2026-10-29 - **Apply:** https://job-boards.greenhouse.io/skylighthq/jobs/4747398005 ## Job description ## 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, software engineers design, implement, and maintain software systems to improve government services for users. This software is built to meet the needs of regular users of government services as well as Skylight’s partners in government. Legacy modernization engineers specialize in migrating, refactoring, or replacing legacy government systems with little to no downtime. Skylight is partnering with a U.S. Air Force program office that runs a portfolio of civil engineering systems. These systems serve users across civil engineering, security forces, and services, including readiness managers, range personnel, and fire and emergency services. Releases are slow today. Regression testing is manual, security review happens after development finishes, and code freeze to production can take a month or more. We’ll move the program to an outcome-driven model with test automation and security built into the pipeline, starting with migrating the first application onto a DoD software factory. Leadership wants this office to become the model other Air Force offices adopt. In this role, you’ll refactor and migrate aging Air Force web applications while keeping them running for the people who depend on them, and you’ll explain the technical tradeoffs clearly enough that government stakeholders can make good decisions. What to know going in Your first 30 days are about working with the Skylight team and government personnel, learning how the program office gets changes to users today, and understanding where testing and security slow things down. This is new work that replaces a traditional support model, so part of the job is coaching your government partners to keep these practices running after we leave. Expect to work alongside government engineers and other contractors, with tools and processes changing as the work gets underway. 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 - Refactor and migrate legacy web applications onto a DoD software factory, with little to no downtime for users - Engineer software as part of a cross-functional team of researchers, designers, product managers, and other engineers - Achieve technical excellence by advocating for and adhering to lean-agile engineering practices such as simple design, continuous integration, version control, and automated testing - Analyze systems to identify technical debt, instability, and other opportunities for improvement, and design, document, and communicate solutions - Explain technical tradeoffs clearly to non-technical stakeholders and help them make decisions in a complex, multi-vendor environment - Pair with and coach government engineers and incoming military developers so modern practices stick after we leave ## What we’re looking for ## Basic qualifications - Ability to write clean, working, and reusable code - Can produce high-quality code by adhering to good practices such as automated testing - Familiar with how to build secure, compliant software and defend against common vulnerabilities - Possess a foundational understanding of data engineering, including how to use various datastores to handle persistent data in software systems - Understand the different pieces of software systems and how to fit them together, while keeping performance, reliability, and availability in mind - Understand the importance of always putting users at the center of your work, including thinking through the impact and implications of any code that you write - Experience shipping production software in a modern web stack, including refactoring or migrating legacy web applications - Experience working in a government or regulated environment with formal security authorization (ATO) - Experience working on cross-functional teams (product, design, engineering, ops) in iterative delivery - A track record of staying aligned and accountable on remote teams - A mindset and work approach that aligns with our [core values](https://skylight.digital/company/values/) Nice-to-haves - Angular experience - Experience migrating applications to the cloud or a DoD software factory (Cloud One, MDaaS, Platform One, or similar) - Experience testing COTS-based systems such as Esri or IBM TRIRIGA - Experience writing automated tests and working in CI/CD, ideally GitLab CI - Experience using AI-assisted development tools, paired with disciplined code review - Experience delivering technology in government, regulated industries, or other public-benefit settings 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 a Common Access Card (CAC) and any special access required for this contract. - 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 This role includes occasional travel to Montgomery, AL, and other U.S. Air Force bases. Expected start date We’re targeting a start date of November 30, 2026, pending contract award. 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 Software Engineer at Skylight, the current salary ranges are as follows: - Associate Software Engineer: $90,000–$125,000 - Software Engineer I: $120,000–$140,000 - Software Engineer II: $135,000–$160,000 - Senior Software Engineer: $150,000–$185,000 - Staff Software Engineer: $170,000–$203,000 - Principal Software Engineer: $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) - 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](https://skylight.digital/careers/join/#interview-process) to learn more about how our interview process works. - Check out our [Career Pathways framework](https://skylight.digital/careers/career-pathways/) to learn more about the different roles within Skylight and the skills needed to do them. - Browse our [case studies](https://skylight.digital/work/experience/) 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 recruiting@skylight.digital. 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. ## About Skylight ## Company Overview - **One-liner**: Skylight is a digital consultancy that helps government agencies deliver better public services through human-centered design, lean-agile engineering, and digital transformation. - **Entity Type**: Private (startup stage; offers stock options) - **Headquarters**: Sarasota, Florida, USA (distributed/remote team across 34 states) - **Founded**: June 2017 - **Founders**: Chris Cairns (President, co-founder of 18F and Technology Transformation Services) ## Core Business - **Primary industry/industries**: Digital government consulting; public sector digital transformation - **Target customers**: U.S. federal, state, and local government agencies (e.g., Veterans Affairs, immigration services) - **Mission or purpose statement**: “Make government work in a digital world” – helping agencies become digital-first through culture change, modern practices, and empowered talent. ## Products & Services Skylight offers professional services, not packaged products. Key service areas: - **Digital Strategy & Transformation**: Roadmaps, operating model design, and organizational change management. - **Human-Centered Design & Research**: User research, service design, and accessible interface design. - **Lean-Agile Engineering**: Custom software development, DevOps, cloud migration, and modern infrastructure. - **Data Science & Engineering**: Data pipelines, analytics, and machine learning for public-sector use cases. - **Security & Compliance**: Security engineering, FedRAMP readiness, and zero-trust architecture. - **Procurement & Acquisition**: Helping agencies buy digital services effectively using modern contracting methods. ## Market Standing - **Valuation/Market Cap**: Not publicly available - **Key Metric**: Team size of 164 people (as of latest update); no public revenue or funding data - **Notable Investors/Partners**: Co-founded the **Digital Services Coalition**; no external investors disclosed (appears bootstrapped) - **Growth Signals**: Growing headcount (164 people across 34 states), expanding client base to include Canadian government (Ottawa), active hiring for multiple senior/staff roles ## Competitive Advantages - **Deep government DNA**: Leadership and many team members came from 18F, U.S. Digital Service, and Presidential Innovation Fellows – giving them insider knowledge of how government works. - **Culture-first approach**: Openly shares knowledge, treats every interaction as a teaching opportunity, and prioritizes culture change as a core part of transformation. - **Distributed & remote-native**: Built as a remote-first company from the start, allowing them to attract top talent nationwide. - **Public-service mission**: Employees are driven by impact, not profit – creating strong alignment with government clients. ## Strategic Focus - **Scaling digital mastery**: Helping agencies institutionalize modern practices (human-centered design, lean-agile) rather than just delivering projects. - **Expanding into defense & security**: Actively hiring a Vice President of Defense & Security, indicating a push into national security clients. - **Building the talent pipeline**: Offering paid internships and apprenticeships to grow the next generation of civic tech practitioners. ## Why Work Here - **Mission-driven work**: Directly improve public services for veterans, immigrants, and millions of other citizens. - **Remote-friendly & flexible**: Distributed team across 34 states; decide when, where, and how to work. - **Competitive compensation**: Salary, stock options (stake in company), performance rewards, referral bonuses. - **Benefits**: 401(k) match up to 10% of salary; up to $2,000/year professional development budget; up to 12 weeks paid parental leave; medical/dental/vision with significant premium coverage; life insurance; HSA/FSA. - **Time off**: Flexible PTO (≈25 days/year) plus 11 paid federal holidays. - **Tech & swag**: Annual tech budget up to $750; $100 swag budget. - **Culture**: Strong emphasis on growth mindset, inclusivity, and continuous improvement; code of conduct; community involvement (charitable donation match up to $500/year). - **Hiring process**: All interviews via video; focuses on getting to know you, not trick questions; accommodations available. ## Sources 1. [skylight.digital - Home](https://skylight.digital/) 2. [skylight.digital - Join Us](https://skylight.digital/careers/join/) 3. [skylight.digital - Team](https://skylight.digital/company/about/) 4. [Greenhouse - Jobs at Skylight](https://job-boards.greenhouse.io/skylighthq) ## Other roles at Skylight - [Senior/Staff/Principal Data Scientist (HHS)](https://feeny.ai/job/senior-staff-principal-data-scientist-hhs-skylight-united-states-q0js4xyk5tx4) — United States - [Staff Product Manager (HHS)](https://feeny.ai/job/staff-product-manager-hhs-skylight-united-states-jc2c8d2mzy3e) — United States - [Staff Product Manager, Technical (HHS)](https://feeny.ai/job/staff-product-manager-technical-hhs-skylight-united-states-0nhe9d7xw3ct) — United States - [Senior/Staff Software Development Engineer in Test (SDET) (U.S. Air Force)](https://feeny.ai/job/senior-staff-software-development-engineer-in-test-sdet-u-s-air-force-skylight-ydbhemwastd3) — United States - [Senior/Staff DevOps Engineer (U.S. Air Force)](https://feeny.ai/job/senior-staff-devops-engineer-u-s-air-force-skylight-united-states-azrcwqyzhz94) — United States - [Senior/Staff Security Engineer (U. S. Air Force)](https://feeny.ai/job/senior-staff-security-engineer-u-s-air-force-skylight-united-states-v2m8een9rtm5) — United States - [Senior/Staff Data Scientist (ACF)](https://feeny.ai/job/senior-staff-data-scientist-acf-skylight-united-states-vpgdz0v6tsj7) — United States - [Senior/Staff Product Manager, Technical (ACF)](https://feeny.ai/job/senior-staff-product-manager-technical-acf-skylight-united-states-rpse69ggwnf2) — United States - [People Operations Manager](https://feeny.ai/job/people-operations-manager-skylight-united-states-sdj4apmmsag5) — United States - [Senior/Staff Product Manager (U.S. Air Force)](https://feeny.ai/job/senior-staff-product-manager-u-s-air-force-skylight-united-states-jc4pyy6pgcnm) — United States