Principal Engineer
Learning.com
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, develop practical life skills, and foster more meaningful connections with others. We support this mission by attracting, developing, and retaining exceptional employees with diverse experiences, backgrounds, and perspectives.
Since 1999, Learning.com has served millions of students across the U.S. and worldwide through engaging digital literacy lessons, professional development, and an easy-to-use SaaS platform. Our curriculum helps students build essential skills in digital citizenship, computer science, coding, AI literacy, and safe, responsible technology use.
POSITION OVERVIEW
We are seeking an experienced, hands-on Principal Engineer to serve as a technical leader across our engineering and IT infrastructure teams. In this role, you will bridge software development, cloud infrastructure, and operational excellence—shaping how Learning.com builds, deploys, and scales high-quality services.
You will influence architecture decisions, guide engineers on modern cloud-native patterns, support high-quality delivery pipelines, and stay close to the code to solve complex system challenges. This role is ideal for someone who thrives in both strategic design and practical implementation, and who enjoys making systems more reliable, observable, and efficient.
WHO YOU ARE
- You are passionate about helping students create healthy & proficient relationships with technology
- You are hungry, humble & 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 AI, cloud-native engineering, and modern DevOps practices
- You take pride in making complex systems simpler, safer, and more reliable
WHAT YOU’LL DO
AI Leadership & Transformation
- Stay current with advancements in AI, machine learning, and developer productivity tools, and assess their potential impact on our engineering and infrastructure practices
- Lead the adoption of AI-driven development workflows, guiding engineers and IT staff in leveraging tools such as GitHub Copilot, ChatGPT, and other emerging platforms
- Partner with senior leadership to define and evolve our AI-first engineering strategy, contributing to team guidelines, enablement programs, and governance guardrails
- Mentor and coach team members on effective AI usage to increase efficiency, code quality, and developer satisfaction
- Identify opportunities to integrate AI into our CI/CD pipelines, observability stack, automation patterns, and operational processes
Technical Leadership & Architecture
- Collaborate with software engineers to design applications that are scalable, observable, and deployment-ready from the start
- Influence system design and implementation decisions to align with cloud-native and microservices best practices
- Define service boundaries and containerization strategies to support performance, reliability, and maintainability
Cloud Infrastructure & Delivery
- Develop and maintain CI/CD pipelines that integrate seamlessly into development workflows
- Implement and refine instrumentation, logging, and monitoring to improve visibility into system health
- Define and manage AWS infrastructure using Infrastructure-as-Code tools such as Terraform or CloudFormation
- Support engineers in runtime diagnostics, performance tuning, and resilient system design
- Troubleshoot complex issues spanning code, containers, networking, and AWS services
- Respond quickly to production issues and participate in the incident response process
Cross-Team Collaboration & Support
- Partner with Security and IT to ensure deployments meet compliance requirements (SOC 2, FERPA, COPPA)
- Work with development teams to embed best practices for operability, scalability, and efficiency
- Create documentation, architecture diagrams, deployment guides, and standards for consistency and shared understanding
WHAT YOU’LL BRING
- 8+ years of software engineering experience, including influence over system design and architecture
- Experience providing technical leadership or mentorship across engineering and infrastructure teams
- Strong programming background in C# and the ASP.NET Core framework
- Proficiency with AWS services and cloud-native application design, preferably using ECS
- Hands-on experience with Infrastructure-as-Code tools such as Terraform or CloudFormation
- Strong understanding of observability practices including metrics, tracing, and centralized logging
- Familiarity with networking, load balancing, service orchestration, runtime configuration, and distributed system concepts
- Experience implementing CI/CD pipelines (GitHub Actions, Jenkins, or similar)
- Experience working in a SaaS production environment with a passion for reliability, performance, and automation
- Familiarity with front-end frameworks such as React or Angular is beneficial for cross-stack collaboration
REPORTING & DETAILS
Reports to: Director or VP-level Engineering Leadership
Department: Engineering & IT
Supervisory Responsibilities: Individual Contributor
Location: Remote
Salary Range: $175k- $185k annually
WE CARE ABOUT YOU
We foster a culture where people bring their full, authentic selves to work every day. We offer a competitive and comprehensive benefits package including:
- Medical, dental, and vision coverage
- 401(k) with company match
- Short- and long-term disability and life insurance
- Employee Assistance Program
- Flexible Spending and Health Savings Accounts
- Health, wellness, and professional-development benefits
EQUITY & INCLUSION
We are serious about our commitment to Inclusion, Diversity, Equity, and Awareness. All applicants will be considered for employment without attention to race, color, religion, sex, national origin, veteran status, disability, pregnancy, gender expression or identity, sexual orientation, or any other protected status. Reasonable accommodations are available upon request.