Trailhead is the engine powering the next generation of digital learning, and we are looking for a Senior Engineering Manager to lead the team 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.
Our mission includes revolutionising how the world learns by integrating agentic learning and bite-sized micro-learning directly into the flow of work within Slack, making skill development both autonomous and instantaneous. In this role, you will lead a distributed, collaborative team of front-end and full-stack engineers dedicated to scaling this learning ecosystem exponentially.
You will be responsible for fostering a culture of transparent communication, high-quality code reviews, and continuous feedback, ensuring that Trailhead remains the most engaging and effective way for our customers and partners to learn.
Technically, you will guide the evolution of our platform as we blend our core stack with Salesforce’s latest innovations. While our foundation is built on Ruby on Rails and React deployed on Heroku, we are strategically pivoting toward Salesforce’s own Lightning Web Components (LWC) off-core to create a seamless experience for our Trailblazers. You will leverage your deep technical expertise to oversee this transition, ensuring that our technical content, developer events, and hands-on workshops are delivered through a high-performance, scalable engine. Your leadership will be vital in helping our engineers "skill up" on this modern stack while maintaining the stability and fun factor that defines the Trailhead brand.
The ideal candidate is a self-starter who thrives on ownership and can navigate the pressures of a fast-paced project portfolio with a great sense of humor. Success in this position requires more than just technical management; you must be an effective collaborator who can provide insightful feedback on projects outside your immediate domain and possess exceptional communication skills to align a distributed workforce. We value leaders who don't just manage but influence, helping to transform Trailblazers into Agentblazers who drive real change within their organizations. If you are passionate about building the workforce of the future and want to lead a team where learning is integrated into every line of code, we invite you to explore our app and join the movement.
Responsibilities:
Manage and develop a team of talented engineers Recruit, nurture and retain best-in-class talent Champion and drive the adoption of Agentic Engineering practices across the team to increase delivery speed and code quality. Provide technical guidance, career development, and mentoring to team members Participate in cross-functional coordination, planning, and reviews with leads from other engineering teams Influence and compellingly communicate the vision to a wide variety of key stakeholders Build strong partnerships across disciplines, such as Design, Product, and Marketing Drive the execution and delivery of features by collaborating with many cross functional teams, architects, product owners and engineers Proactive in foreseeing issues and resolve it before it happens Daily management of standups as the ScrumMaster for engineering teams Ensure teams have clear priorities and adequate resources Work effectively as part of a geographically distributed team
Required Skills:
Leadership & Management: Proven ability to lead, motivate, and grow high-performing engineering teams in a challenging, dynamic, and global environment. Experience managing teams that leverage AI-assisted development tools (Claude, Cursor, etc.) to optimize the software development lifecycle. Technical Stack: Strong professional experience with Ruby on Rails and React, including proficiency in NodeJS, JavaScript, HTML, and REST/SOAP APIs. Architecture & Design: Experience leading design and architecture discussions and collaborating with product management and technical teams to translate requirements into software features. Software Lifecycle: Expertise in the full software development lifecycle, including short release cycles for products released for public consumption. Engineering Best Practices: Deep working knowledge of coding standards, code reviews, SCM, CI/CD build processes, testing, and operations. Agile Methodology: Practical experience working within Agile development environments. Communication: Excellent oral and written communication skills with the ability to describe complex technical features to diverse stakeholders. Soft Skills: A nimble, proactive approach with the comfort to work under minimal specifications and handle multiple tasks simultaneously.
Desired Skills:
Distributed Leadership: Specific experience managing and mentoring remote or distributed teams with a focus on transparent, asynchronous communication. Modern Web Transitions: Experience guiding architectural transitions, specifically moving from legacy frameworks toward Lightning Web Components (LWC). Strategic Ownership: The ability to take full accountability for a project portfolio while maintaining a positive, resilient team culture under pressure. Operational Excellence: Advanced understanding of modern deployment workflows, specifically using platforms like Heroku. Multidisciplinary Adaptability: A "skill-up" mindset with the curiosity and competence to provide feedback on projects outside your primary domain of expertise.
Minimum Requirements:
7-12+ years of enterprise software engineering management experience at an enterprise technology company.
