Principal Engineer
Make a Difference
At Learning.com, we believe that when K–12 students, regardless of their circumstances, develop healthy and proficient relationships with technology, they are better equipped to improve academic outcomes, build practical life skills, and foster more meaningful connections with others. Since 1999, we’ve supported millions of students through engaging curriculum and a scalable SaaS platform focused on digital literacy, computer science, AI literacy, and responsible technology use.
Position Overview
We are seeking an experienced Principal Engineer with a deep foundation in application engineering and system architecture, who has extended that foundation into cloud-native, containerized environments on AWS. This is an architect-first, code-adjacent role. You will be a day-to-day technical authority for backend application architecture and the containerized runtime those applications operate within. You will partner closely with engineering, IT operations, and leadership to design, evolve, and harden the systems that power our SaaS platform. While you will not be expected to deliver features as a primary responsibility, you must be capable of diving into complex codebases, contributing to prototypes and spikes, and unblocking teams when architectural or runtime complexity demands it.
Who You Are
- You are passionate about helping students create healthy and proficient relationships with technology
- You are hungry, humble, and smart
- You thrive in a dynamic, fast-paced environment with evolving priorities
- You collaborate deeply, challenge constructively, and value continuous learning
- You are energized by modern application architecture, cloud-native engineering, and AI-enabled development workflows
- You take pride in making complex systems simpler, safer, and more reliable
What You'll Do
AI Enablement & Engineering Workflows
- Act as the senior technical champion for AI-enabled development practices across the engineering organization
- Evaluate and guide the responsible use of AI tools in software design, coding, testing, and troubleshooting workflows
- Mentor senior and staff engineers on using AI tools effectively to improve code quality, velocity, and system understanding
- Stay current on AI-assisted software engineering trends and assess when they are production-ready and valuable for the organization
Application Architecture & Engineering Leadership
- Serve as a subject matter expert in backend system architecture for a modern SaaS platform
- Design and evolve service boundaries, APIs, data access patterns, and asynchronous workflows
- Guide teams on scalable, maintainable application patterns
- Review designs and code with an architectural lens, identifying long-term risks and tradeoffs
- Partner with engineers to ensure applications are production-ready from day one
Cloud-Native Runtime & Containerization
- Own and evolve the containerized runtime architecture for our services
- Lead decisions around container orchestration and deployment strategy (e.g., Docker Swarm vs AWS ECS)
- Define how applications are packaged, configured, deployed, and operated in AWS
- Partner with IT Operations on infrastructure concerns while owning the application runtime model
- Ensure services are observable, diagnosable, and resilient in production
AWS & Delivery Enablement
- Design application-level usage of AWS services to support scalability, reliability, and cost awareness
- Collaborate on Infrastructure-as-Code approaches (CloudFormation or Terraform)
- Shape CI/CD pipelines to support containerized services and safe deployments
- Support incident response and root cause analysis when architecture or runtime behavior is involved
Cross-Functional Collaboration
- Work closely with IT, Security, and Engineering leadership to align architecture with compliance needs (SOC 2, FERPA, COPPA)
- Create clear documentation, architecture diagrams, and standards to support consistency across teams
- Act as a trusted technical advisor to engineering managers and senior leadership
What You'll Bring
Required Experience
- 8+ years of professional software engineering experience
- Demonstrated ownership of application architecture in production SaaS environments
- Deep experience with C# and ASP.NET Core in real-world systems
- Sufficient JavaScript/TypeScript experience to collaborate effectively on full-stack architecture and review front-end implementations
- Hands-on experience deploying and operating containerized applications on AWS
- Practical knowledge of ECS (preferred) or comparable container orchestration approaches
- Proven ability to collaborate effectively with infrastructure and IT partners while maintaining a strong application engineering perspective
- Experience with AI-enabled development workflows and tooling
- Experience evaluating or migrating between container orchestration platforms preferred but not required
- Experience in regulated environments (education, healthcare, finance) preferred but not required
Reporting & Details
- Reports to: VP of Engineering
- Department: Engineering & IT
- Supervisory Responsibilities: Individual Contributor
- Location: Remote
- Salary Range: $175,000–$185,000 annually
We care about you
We offer a competitive and comprehensive benefits package including medical, dental, and vision coverage, 401(k) with company match, disability and life insurance, flexible spending accounts, wellness benefits, and professional development support.
Equity & Inclusion
Learning.com is committed to Inclusion, Diversity, Equity, and Awareness. All qualified applicants will be considered without regard to race, color, religion, sex, national origin, veteran status, disability, pregnancy, gender identity or expression, sexual orientation, or any other protected status. Reasonable accommodations are available upon request.
