Engineering Director

Pathstream is seeking an experienced Engineering Director to lead engineering teams and drive technical growth. The role involves advancing AI-native engineering practices and fostering a collaborative culture while managing team performance and strategy execution.

Responsibilities:

• Lead, grow, and develop one or more engineering teams — with an active role in shaping engineering team health and capability beyond your direct reports — accountable for all aspects of people management including coaching, performance reviews, compensation, promotions, and when necessary, performance management
• Independently plan and execute changes to team structure and staffing: identify capability gaps, define new roles, manage team size, and partner with recruiting to attract and close top engineering talent
• Build and sustain a culture of collaboration, ownership, psychological safety, and continuous learning, where engineers feel empowered to experiment with new approaches, including AI-enabled development practices
• Resolve interpersonal and technical conflicts within and across teams; develop engineers at all levels through mentorship, direct feedback, and thoughtful career development
• Operate as a leader through others: elevate the skills and capabilities of those around you and position your team — not yourself — as the driver of execution and momentum
• Serve as a credible voice at the engineering org level — influencing how Pathstream's engineering teams collaborate, prioritize shared work, and build collective capability beyond your direct team
• Own the technical vision and roadmap for your team's domain, ensuring alignment with broader company priorities and the needs of cross-functional partners in product and design
• Drive alignment on cross-team goals and initiatives, independently resolving conflicting priorities across teams without escalation; lead effectively in environments of uncertainty and ambiguity, bringing clarity and structure to complex spaces
• Define what success looks like by setting clear goals, establish measurable outcomes, and track progress so the impact of your team's work on customers and the business is always clear
• Clarify ownership and decision-making across initiatives. Delegate tactical decisions appropriately while maintaining accountability for overall outcomes
• Work across team and service boundaries to lead multi-team initiatives and keep dependent work unblocked, operating independently; proactively adjust team pace to maintain urgency while protecting against burnout and sustaining long-term productivity
• Contribute to the broader engineering organization by actively shaping strategic direction, leading roadmap conversations that span team boundaries, and independently identifying and driving resolution of org-level risks or opportunities — not just escalating them
• Lead by example in an engineering culture where AI is already central to how we build software. You are hands-on with modern AI-enabled development tools (Claude Code, Cursor, GitHub Copilot, and similar AI-assisted development environments) — regularly explore how they can improve engineering workflows
• Drive the adoption of agentic engineering workflows across your team(s) where AI systems assist with or automate multi-step engineering tasks. This may include building internal frameworks, playbooks, or reusable patterns that allow engineers to leverage AI safely and effectively
• Coach engineers on how to collaborate effectively with AI systems
• Partner with engineering leadership to shape Pathstream's evolving AI engineering strategy, including evaluating emerging tools, determining where AI creates the most leverage, and ensuring responsible adoption aligned with internal AI guardrails
• Stay informed about advancements in AI-assisted and agentic development; bringing practical insights back to the team and continuously raising the bar for how engineering teams use AI to improve speed, quality, and impact
• Build strong relationships with stakeholders including product managers, designers, customers, and cross-functional partners. Represent your team's goals, metrics, and progress clearly to senior leadership
• Collaborate closely with engineering teams to ensure seamless integration across systems and enable rapid delivery of impactful features
• Maintain a deep understanding of Pathstream’s business goals and ensure your teams are structured and prioritized to deliver the greatest value
• Promote strong knowledge-sharing practices across teams so that no individual — including yourself — is a single point of failure

Requirements:

• 7–10 years of professional software engineering experience
• At least 4 years of hands-on technical work
• 3–5 years in engineering leadership
• 3+ years directly managing engineers
• Proven track record of successfully leading people, teams, or projects across multiple contexts
• Experience managing or influencing across multiple teams
• Comfortable independently owning the full scope of people management responsibilities
• Familiarity with modern web application stacks including technologies such as: Ruby on Rails, React, JavaScript, Docker, PostgreSQL, and AWS
• Hands-on with modern AI-enabled development tools and agentic engineering approaches
• Understanding of how AI can be incorporated across the software development lifecycle
• Ability to represent and be accountable for the technical output of your team
• Strong understanding of scalability and system design
• Curiosity about the rapidly evolving AI tooling landscape
• Highly collaborative leader with curiosity, humanity, and generosity
• Well-developed stakeholder management skills
• Comfortable operating in environments with ambiguity and shifting priorities
• Energized by working alongside senior individual contributors