Director of Engineering, AllTrails

• 10+ years of experience building and leading high-performing engineering teams, with proven success at scaling organizations through complex technical and organizational challenges
• Deep technical expertise across modern programming languages, frameworks, and platform SDKs (e.g., Swift, Kotlin, Python, Ruby), with sufficient hands-on experience to guide architecture decisions and evaluate technical tradeoffs
• A track record of shipping large-scale, cross-functional projects, balancing business priorities with technical constraints
• Demonstrated experience mentoring and developing engineering managers and senior engineers, with a focus on building future leaders
• Exceptional communication, influence, and collaboration skills, with the ability to align stakeholders across engineering, product, and executive leadership
• Comfortable with modern workflows and tools (GitHub, Jira, Confluence, AI-assisted tooling such as Cursor/Claude)
• Willing to roll up your sleeves, but thoughtful about applying just the right amount of process
• A leader who builds positive culture, values humility and empathy, and understands that the best teams thrive on trust and autonomy
• Strong background in CI/CD, release management, and observability tooling (e.g., Crashlytics, Embrace, New Relic, Datadog)
• Genuine passion for the outdoors and alignment with our mission to connect people to nature
• AI Native: You naturally incorporate AI tools to enhance your work. You’re comfortable writing prompts, evaluating AI outputs, and enjoy experimenting with new ways to boost creativity, productivity, and decision-making

Desirable

• At AllTrails, we’re on a mission to get more people outside and we’re looking for a hands-on Director of Engineering to play a critical part in making that happen
• Reporting directly to our CTO, you’ll have the opportunity to shape how we scale our technology and deliver best-in-class experiences to millions of users worldwide
• This is a high-impact role where you’ll own strategy and execution, collaborate cross-functionally with leaders across the business, and help drive innovation that brings the outdoors closer to everyone
• Lead and inspire a team of frontend, backend, and mobile engineering managers and senior engineers, setting direction and fostering an environment of trust, collaboration, and high performance
• Serve as a strategic and technical leader, representing engineering to executive leadership, product, design, and cross-functional partners
• Drive technical excellence by leading discussions on architecture, design, and long-term platform strategy across iOS, Android, frontend, and backend
• Grow and scale the team by hiring exceptional talent, mentoring future leaders, and ensuring engineers are supported in their career development
• Champion engineering quality and efficiency, advocating for best practices in code, process, and system design while balancing speed and pragmatism
• Foster a culture of continuous improvement and innovation, introducing new technologies, workflows, and approaches to keep engineering at the cutting edge
• Collaborate across engineering, security, data science, product, and marketing to deliver features that delight millions of outdoor enthusiasts
• Champion the thoughtful adoption of AI-powered tools and workflows, driving experimentation and integration of emerging technologies (e.g., AI agents coordinating workflows and code reviews) to improve developer productivity, quality, and innovation