Description
Trailhead is the engine powering the next generation of digital learning, and we are looking for a Principal Engineer to serve as a primary technical visionary for the platform building the biggest shift in software since the cloud. We are currently mobilizing our community as a force multiplier for the "Agentblazer" movement—a global effort to equip leaders and early adopters with the skills needed to navigate an AI-driven world. In this role, you will provide high-level technical direction for a distributed, collaborative team of engineers, ensuring our architecture scales exponentially to meet the needs of millions of global learners. You will be a cornerstone of our technical culture, fostering transparent communication and driving the standards for excellence that keep Trailhead at the forefront of the industry.
As a Principal Engineer, you will serve as the Tech Leader for Agentic Workflows, responsible for setting the global standards for how our organization integrates tools like Gemini and OpenAI into the core Trailhead architecture. You will lead the charge in ensuring our engineering culture remains at the cutting edge of AI-driven innovation. While our foundation is built on Ruby on Rails, Node.js, and React deployed on Heroku, you will be the leader of our strategic evolution toward more modular, high-performance web standards. You will leverage your deep expertise to ensure our transitions result in a seamless experience, overseeing the "learning engine" that delivers high-impact developer events and hands-on workshops. Your leadership will be vital in guiding the entire engineering organization to "skill up" on modern architectures while maintaining the stability, security, and "fun factor" that defines the Trailhead brand.
The ideal candidate is a strategic self-starter who thrives on total ownership of complex technical ecosystems. Success in this position requires the ability to influence far beyond the immediate engineering team, providing insightful feedback on the entire project portfolio and collaborating with executive leadership to align technical roadmaps with business goals. We value visionaries who don't just solve problems but anticipate them, transforming our existing infrastructure into a world-class environment that empowers the next generation of Agentblazers.
Responsibilities:
Technical Strategy: Define the long-term technical roadmap for Trailhead, ensuring the platform remains scalable, performant, and maintainable as we evolve our frontend architecture.
Innovation Advocacy: Serve as the primary technical influencer for emerging agentic tools and frameworks (e.g., Windsurf, Cursor), identifying opportunities to multiply the team's output and systematically reduce manual technical debt through AI-assisted engineering.
Architectural Leadership:
Lead the design and documentation of complex, multi-system architectures, acting as the final authority on major technical decisions and abstraction strategies.
Team Multiplication: Spend significant time teaching high-level design concepts (SOLID), refactoring skills, and performance techniques to elevate the entire engineering staff.
System Health:
Drive strategies to minimize technical debt across the organization and implement tools and techniques that multiply the output of the global engineering team.
Quality Advocacy: Establish and oversee organizational standards for testing (unit, functional, integration), code reviews, and CI/CD processes to ensure 24/7 reliability.
Cross-Functional Influence: Collaborate with Product Management and Engineering leadership to prioritize backlogs and navigate complex technical dependencies.
Minimum Qualifications:
Experience: 15+ years of professional experience with object-oriented programming (Ruby, Python, Java, or Go).
Architectural Judgment: Deep understanding of well-factored code; ability to lead high-level architectural trade-off discussions (e.g., Monolithic vs. Microservices) and mentor the team on SOLID principles.
Agentic Engineering & AI Mastery: Champion, influencer, and early adopter of Agentic Engineering. Proficiency in and active adoption of modern AI development tools and LLMs, including but not limited to Claude, Cursor, Windsurf, Gemini, and OpenAI/OpenAPI to drive engineering velocity and innovation.
Full-Stack Mastery: Extensive experience with Ruby on Rails or an equivalent MVC framework (e.g., Django, Spring Boot, or NestJS) and React.
Datastore Expertise: Vast experience with relational datastores (PostgreSQL, MySQL) and a mastery of relational database design theory and query optimization.
Cloud Operations:
Professional experience deploying and managing mission-critical applications on Heroku or major cloud providers (AWS, GCP, or Azure).
Communication: Exceptional communicator who can explain complex architectural concepts simply to both technical and non-technical stakeholders.
Education: Bachelor’s or Master’s degree in Computer Science or equivalent professional experience.
Preferred Skills:
Modern Web Standards: Proven ability to lead the transition from legacy frameworks to high-performance, native React components integrated with robust design systems.
Advanced Data Strategy: Experience with a variety of datastores beyond relational, such as Redis, Memcached, or CouchDB.
Tooling & Automation: Deep familiarity with TypeScript, Node.js, and end-to-end testing frameworks like Cypress.io or Jest.
Product Vision: A history of working on high-traffic products released for massive public consumption with an obsession for detail and user experience.
Strategic Mentorship: Experience growing global, distributed engineering teams through influential leadership and a "skill-up" mindset.