The Role
Develop and scale full-stack, AI-enabled enterprise systems supporting CMS modernization. Responsibilities include designing Python and React applications, RESTful APIs, microservices, NLP and LLM integrations, CI/CD pipelines, cloud-native deployments, performance optimization, observability, testing, secure coding, and architectural leadership. The role collaborates with design, product, data science, and DevOps teams to improve healthcare services and automate operational processes.
Summary Generated by Built In
We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.
We stand by our values, and we won’t compromise on any of them.
Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.
Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally.
Inquisitive: We remain students by failing openly and turning lessons into solutions.
Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.
Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.
Because of that, we continue Onward, Upward, and Skyward.
We need a Senior Software Engineer.
Are you the person people call when their architecture won’t scale? When their API design feels “off”? When their frontend needs to actually make sense to a human? Do you push beyond “it works” into “it’s elegant, scalable, and built for the future”? If you’re driven by innovation and energized by experimenting with emerging technologies (especially AI-powered solutions) we want to talk to you.
This isn’t just another engineering role. This is an opportunity to build intelligent, human-centered systems that modernize how one of the nation’s largest healthcare agencies serves millions of Americans.
Come join us if you're motivated to learn from others, to learn from mistakes, to be part of a future-looking and growth-oriented team.
Let's go Skyward together.
What you’ll do:
- Serve as a senior engineer supporting CMS’s modernization efforts — reducing manual effort, improving data accuracy, and enhancing transparency through scalable, AI-enabled enterprise systems.
- Design, build, and scale full-stack applications using modern backend frameworks (Python/FastAPI or similar) and dynamic frontend technologies (React or comparable frameworks).
- Architect and implement RESTful APIs and microservices that power intelligent features leveraging NLP and large language models (LLMs).
- Collaborate closely with Human-Centered Design (HCD) experts to deliver intuitive, responsive, and accessible user experiences that truly serve real people.
- Lead backend development efforts focused on performance optimization, observability, reliability, and clean architecture patterns.
- Build and enhance CI/CD pipelines (Jenkins or similar tools), ensuring automated testing, code quality enforcement, and secure deployments in cloud-native environments.
- Troubleshoot complex system issues, debug test failures, improve test coverage, and raise the bar for engineering quality across the team.
- Identify high-impact automation opportunities that meaningfully reduce operational burden for end users and stakeholders.
- Contribute to architectural decisions, technical roadmaps, and engineering best practices across the program.
- Partner cross-functionally with product, customer experience, data science, and DevOps teams to align technical implementation with mission outcomes.
What we’d like you to have:
- Bachelor’s degree in computer science, information systems, or related field (or equivalent practical experience).
- 10+ years of progressive software engineering experience building and scaling production-grade applications.
- Strong backend expertise in Python and modern API frameworks (FastAPI, Flask, Django, or similar).
- Solid frontend experience with React (or comparable modern JavaScript frameworks) and component-driven development.
- Experience designing RESTful APIs and working within microservices architectures.
- Hands-on experience with CI/CD pipelines (Jenkins or similar), automated testing frameworks, and secure code deployment practices.
- Familiarity with AWS cloud environments and cloud-native development patterns.
- Experience integrating or supporting AI/ML-driven capabilities (NLP, LLMs, chatbots, or similar intelligent systems).
- Strong understanding of software design principles, clean architecture, and secure coding practices.
- Ability to translate complex technical concepts into language that resonates with cross-functional stakeholders.
- A proactive mindset: someone who sees opportunities for improvement and takes initiative
What would blow us away:
- Experience building or supporting AI-powered enterprise applications in regulated environments (federal, healthcare, or similar).
- Familiarity with MLOps workflows or integrating model APIs into production systems.
- Experience modernizing legacy enterprise systems into scalable cloud-native architectures.
- Knowledge of ethical AI considerations and regulatory requirements.
- Previous experience supporting CMS or other HHS agencies.
Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box.
And now the important part. What we offer you:
- Medical, dental, vision insurance
- 15 days of paid leave
- 7 days of sick leave
- 2 days bereavement leave
- 11 paid Federal holidays
- Up to 40 hours for jury duty
- 401K with 4% employer contribution (and no vesting period)
- Up to 4 weeks of paid paternity and maternity leave
- Company provided laptop
- $5,000 per year for professional development
- $600 per year for technical supplies and equipment
- $2,000 referral bonus
- Life and disability insurance
- HSA and FSA
- Legal Shield and ID Shield Voluntary Benefits
- Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions. Who says government work can't be exciting!
At Skyward, we support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees.
Offers of employment with Skyward are contingent upon acceptable results of a background investigation.
Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor.
Skills Required
- Bachelor’s degree in computer science, information systems, or a related field, or equivalent practical experience
- 10+ years of progressive software engineering experience building and scaling production-grade applications
- Strong backend expertise in Python and modern API frameworks such as FastAPI, Flask, or Django
- Frontend experience with React or comparable modern JavaScript frameworks
- Experience designing RESTful APIs and working with microservices architectures
- Hands-on experience with CI/CD pipelines, Jenkins or similar tools, automated testing, and secure deployment practices
- Familiarity with AWS cloud environments and cloud-native development patterns
- Experience integrating or supporting AI/ML capabilities, including NLP, LLMs, or chatbots
- Understanding of software design principles, clean architecture, and secure coding practices
- Ability to communicate complex technical concepts to cross-functional stakeholders
- Proactive mindset with initiative to identify improvement opportunities
- Experience building or supporting AI-powered enterprise applications in regulated environments
- Familiarity with MLOps workflows or integrating model APIs into production systems
- Experience modernizing legacy enterprise systems into scalable cloud-native architectures
- Knowledge of ethical AI considerations and regulatory requirements
- Previous experience supporting CMS or other HHS agencies
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The Company
What We Do
Skyward IT Solutions, LLC is a technology services provider specializing in AI-driven government services and digital modernization for federal and public sector operations. Founded in 2013, the company delivers secure, scalable, and user-centered solutions including custom AI agents, cloud engineering, and agile software development, focusing on improving service delivery and operational efficiency for agencies such as CMS and the SBA.
