Job Title: Principal Engineer
Location: U.S. Remote – preferred US-based time zones, CST or EST
Company Description:
CYPHER Learning is leading the necessary disruption of learning platforms to unleash human potential with modern learning experiences. We exist to ignite lifelong learning passions through personalized, engaging, and limitless learning experiences for all, giving L&D pros and educators more time to teach and train, building human connection into everything we do, and delivering tailored learning experiences that are meaningful and measurable. We are a fast-growing company with a passion for education and technology.
Position Overview:
As Principal Engineer at CYPHER Learning, you will serve as a senior technical leader responsible for shaping the architecture, scalability, and long-term technical direction of our platform and products. You will lead the design of large-scale software systems, solve complex engineering challenges, and drive critical technical initiatives that strengthen reliability, security, and overall product performance. This role blends deep technical expertise, architectural judgment, and hands-on execution, ensuring technical decisions support business priorities while positioning CYPHER for long-term scale. You will partner closely with engineering, product, and cross-functional teams to guide technical direction, elevate engineering standards, and ensure our systems are built to adapt and grow with the business.
What You Will Do:
- Provide technical leadership and strategic direction for large-scale software systems across CYPHER products.
- Architect scalable, high-performance solutions aligned with long-term platform and business goals.
- Solve complex technical challenges while ensuring reliability, security, and maintainability.
- Establish and drive adoption of engineering standards, particularly in object-oriented design, testing, error handling, and query architecture.
- Lead technical direction across teams through influence, shaping architectural decisions and engineering priorities.
- Act as a force multiplier by coding at a high level while elevating team capability, quality, and output.
- Mentor engineers at all levels and strengthen technical judgment across the organization.
- Own 1–3 year technical direction, balancing platform health, scalability, and business value.
- Evaluate build-versus-buy decisions, upgrades, and refactoring against technical and organizational constraints.
- Identify and address platform-wide risks, including performance, security, and long-term maintainability.
- Exercise strong technical judgment, including challenging decisions that may compromise long-term platform health.
- Lead technical risk assessment for critical initiatives, providing clear estimates and tradeoffs that support effective planning.
- Identify security gaps across application and infrastructure layers and prioritize remediation based on business and technical risk.
- All other duties as assigned.
Required Skills & Experience:
- Bachelor’s or master’s degree in Computer Science, Engineering, or a related field.
- 12+ years of software engineering experience, including deep technical leadership in complex product environments.
- Proven experience architecting and scaling large distributed software systems in production environments.
- Deep mastery of the primary framework (Rails), including internals, request lifecycle, ActiveRecord, middleware behavior, and where abstractions break at scale.
- Strong full-stack proficiency across Ruby, Rails, JavaScript, and TypeScript.
- Deep knowledge of cloud platforms, microservices architecture, and containerized environments, including Docker and Kubernetes.
- Strong understanding of performance optimization, security, reliability, and maintainability in large-scale systems.
- Exceptional problem-solving skills, with a track record of resolving complex technical challenges.
- Demonstrated problem-solving capability in high-pressure situations, with the ability to investigate complex issues, adapt as priorities evolve, and drive effective technical resolution.
- Strong attention to detail and organizational judgment, enabling effective prioritization across competing technical initiatives and dependencies.
- Demonstrated ability to mentor senior engineers and influence technical direction across teams.
- Excellent communication skills, with the ability to translate complex technical concepts into clear decisions and recommendations.
- Product-minded and continuously curious, with a positive approach to learning, evolving technologies, and improving engineering outcomes.
Our Values:
Curiosity: Continues learning to stay agile and innovative.
Connection: Embracing and celebrating our differences.
Empowerment: Rewarding positive people-centric behaviors and decisions.
Potential: Challenging the status quo and pushing for what is possible.
Impact: Making a positive impact for our clients and communities around the world.
Equal Employment Opportunity
At CYPHER Learning, we believe diversity is essential to innovation and progress. We are committed to creating a workplace where individuals of all backgrounds, identities, and experiences are respected, included, and empowered to thrive. Our culture is built on connection, curiosity, empowerment, potential, and impact—and we know that these values are only fully realized when everyone has a seat at the table.
CYPHER Learning is proud to be an Equal Opportunity Employer. We make all employment decisions based on merit, qualifications, and business needs—without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, veteran status, genetic information, or any other protected status under applicable law. As a global, remote-first company, we embrace flexibility and accessibility in every aspect of how we work. If you require a reasonable accommodation during the application or interview process, please contact our People team at [email protected]. We are committed to providing an inclusive and equitable experience for every candidate.