Principal Engineer

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 Principal Engineer.

Do you like pushing the boundaries of technology? Do you love staying on top of the world of artificial intelligence because of how it can make our lives easier? If you’re someone who’s driven by innovation and who loves experimenting with emerging technologies, 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.

• Help us ship our first customer-ready product in 90 days while establishing the technical foundation for scale.
• Be our Swiss Army knife who can architect solutions, write production code, deploy infrastructure, and translate complex domain expertise into elegant software.
• Partake in architecture and technical strategy: design system architecture for AI-first automation platform integrating LLM APIs; make critical technical decisions on frameworks, patterns, and infrastructure; translate SME domain knowledge into scalable technical solutions; balance speed-to-market with technical sustainability.
• Hands-on development: build full-stack web applications; implement prompt engineering strategies and agentic workflows; write production-quality code across the stack; develop reusable components and services for AI automation.
• DevOps and infrastructure: own AWS infrastructure strategy and implementation; build and maintain CI/CD pipelines for rapid iteration; implement IaC; handle release management and production operations; ensure security, reliability, and cost-efficiency.
• Customer-facing technical work: build compelling demos and POCs for sales enablement; participate in early customer technical discovery; iterate on feedback to refine product-market fit; support early customer implementations.
• If all that wasn’t enough, we’ll also need you to do some domain translation, where you will work closely with SMEs to understand complex domain problems, bridge the gap between business requirements and technical implementation, and rapidly prototype solutions to validate product hypotheses.

• Bachelor’s degree in computer science, engineering, mathematics, or related field.
• Minimum of 7 years of experience in software engineering, with progressive movement into senior roles.
• Experience taking products from concept to customers.
• Strong backend skills with solid frontend fundamentals (Svelte, Python, Typescript/Javascript).
• Deep knowledge of AWS services (Lambda, ECS/EKS, S3, RDS, etc), architecture patterns, and best practices.
• LLM/AI implementation experience, including working with LLM APIs in production, prompt engineering and optimization, and building agentic systems or AI workflows.
• Infrastructure experience with Terraform/CDK, GitHub.
• Database experience with PostgreSQL, Vector databases (Pinecone/Weaviate/similar).
• A knack for explaining technical concepts to non-technical stakeholders. Your communication skills are second to none.

• You have experience with RAG systems, vector databases, or embeddings.
• You have prior experience scaling AI products from prototype to production.

• 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 are committed to creating an environment where everyone, regardless of gender, race, ethnicity, sexual orientation, disability, or background, can thrive. We support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees, including caregivers and those with unique needs.

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.