The Role
Lead architecture and technical vision to merge and modernize CMS systems on AWS. Design modular, containerized, IaC-driven platforms with CI/CD, observability, disaster recovery, and LLM/automation capabilities. Guide migrations, apply modern patterns (strangler-fig), translate stakeholder needs, and provide technical leadership and mentorship to engineering teams.
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 Solutions Architect.
Do you see the whole board - the systems, the data, the dependencies, and the business goals behind them - and know exactly where the next move should go? Are you the kind of engineer-leader who can sketch a modern architecture on a whiteboard in the morning, defend the trade-offs to stakeholders by noon, and roll up your sleeves with the dev team by afternoon? If you love turning sprawling, complex environments into clean, scalable, modern systems, and bringing a team along with you, then please apply.
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:
- Lead the technical vision for the Centers for Medicare & Medicaid Services (CMS) as it merges and modernizes its enterprise knowledge and data systems into a single, AI-driven platform, reducing manual effort, improving data accuracy, and enhancing transparency for stakeholders.
- Own the architecture. Design a robust, modern enterprise architecture built on AWS, guided by the AWS Well-Architected Framework, the USDS playbook, and Twelve-Factor App principles, while minimizing on-premises footprint and maintaining strong disaster recovery.
- Steer a seamless, low-risk transition and ongoing operations, meeting infrastructure and application availability SLAs without disrupting CMS’s core business.
- Merge two systems without breaking either. Apply patterns like strangler-fig and cyclomatic-complexity analysis to identify, prioritize, and sequence refactor, integration, and modernization opportunities.
- Design for change. Build modular systems using containerization, infrastructure as code, and CI/CD so the platform can flex with CMS’s evolving strategies and new initiatives.
- Partner with the AI Lead to identify and architect automation opportunities, including LLM-driven and automated data-collection strategies.
- Establish observability and insight. Work with the team to stand up continuous monitoring (CloudWatch, New Relic, Splunk) and turn performance, health, and cost data into decisions.
- Be the bridge between technology and business. Translate stakeholder needs into technical direction and explain technical trade-offs to non-technical audiences with clarity.
- Provide technical leadership and mentorship. Set engineering standards, guide the development team, and grow the technical capability of the people around you.
What we’d like you to have:
- A bachelor’s degree in computer science, engineering, or a related field.
- 5+ years of experience in solutions architecture, software engineering, or systems engineering, including significant time architecting AWS cloud environments.
- Deep expertise in AWS services, cloud architecture patterns, and modern best practices.
- Strong command of modern engineering practices - microservices, containerization (Docker), infrastructure as code (Terraform, Ansible), and CI/CD (Jenkins, GitLab CI).
- A track record of leading the technical direction of complex, distributed systems and guiding engineering teams.
- Proficiency in one or more programming/scripting languages (e.g., Python, Bash, Go) and the credibility that comes from having built things yourself.
- Excellent communication skills, with a real talent for presenting complex technical concepts to both engineers and stakeholders.
What would blow us away:
- You’ve previously worked with CMS.
- You have experience working in AI, NLP, or LLM-driven environments - specially hosting models securely within a cloud environment.
- You have familiarity with FISMA boundaries, ATO/cATO, and federal security frameworks (RMF, ARS, IS2P2).
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 (fully paid for employees)
- 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, engineering, or related field
- 5+ years experience in solutions architecture, software engineering, or systems engineering
- Significant experience architecting AWS cloud environments and deep expertise in AWS services
- Strong command of modern engineering practices (microservices, containerization)
- Containerization experience (Docker)
- Infrastructure as Code experience (Terraform, Ansible)
- CI/CD experience (Jenkins, GitLab CI)
- Track record of leading the technical direction of complex, distributed systems and guiding engineering teams
- Proficiency in one or more programming/scripting languages (Python, Bash, Go)
- Excellent communication skills and ability to present technical concepts to non-technical stakeholders
- Ability to obtain and maintain a Public Trust security clearance
- Acceptable results on a background investigation
- Experience with CMS (Centers for Medicare & Medicaid Services)
- Experience working in AI, NLP, or LLM-driven environments and securely hosting models in cloud
- Familiarity with FISMA boundaries, ATO/cATO, and federal security frameworks (RMF, ARS, IS2P2)
- Experience with observability/monitoring tools (CloudWatch, New Relic, Splunk)
Am I A Good Fit?
Get Personalized Job Insights.
Our AI-powered fit analysis compares your resume with a job listing so you know if your skills & experience align.
Success! Refresh the page to see how your skills align with this role.
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.
