Engineering Director

Pathstream•San Francisco, CA

9h•$143,000 - $210,000•Remote

About The Position

Pathstream is seeking an experienced Engineering Director to lead one or more engineering teams and drive the next chapter of our technical growth. This is a senior member of the engineering leadership team reporting to the SVP of Engineering. We are looking for someone who has already built a strong foundation in engineering management and technical delivery, and who now brings the maturity, range, and ambition to operate across teams while influencing strategy, engineering culture, and developer productivity. A core expectation of this role is the ability to advance Pathstream’s AI-native engineering practices. AI adoption is already deeply embedded in how we build software at Pathstream. We are looking for a leader who not only embraces this approach but actively pushes the organization forward in adopting AI-enabled development tools and agentic engineering workflows. Pathstream was founded on the premise that substantial unrealized economic and human potential exists within each organization's frontline workforce. We are reshaping the way employees and managers on the frontlines excel in their careers. In this age of rapid tech evolution, our enterprise partnerships transform frontline teams from transactional to relational, and from task-oriented to strategic. We impact companies' bottom lines with improved productivity, increased retention, and differentiated quality of customer experience — while employees experience greater success in their current roles and unlock future professional growth. We're a tight-knit, hardworking, mission-driven team of ~60 employees eager to scale our solution and transform careers across the United States. Want to learn more?

Requirements

You bring 7–10 years of professional software engineering experience, with at least 4 years of hands-on technical work and 3–5 years in engineering leadership, with 3+ years directly managing engineers
You have a proven track record of successfully leading people, teams, or projects across multiple contexts.
You have experience managing or influencing across multiple teams, or have led a single team through growth and complexity at a scope where you were regularly driving alignment, unblocking cross-team dependencies, and influencing decisions beyond your immediate org
You are comfortable independently owning the full scope of people management responsibilities, including performance management, compensation discussions, career development planning, promotions, and difficult conversations when needed.
You bring familiarity with modern web application stacks similar to ours, including technologies such as: Ruby on Rails, React, JavaScript, Docker, PostgreSQL, and AWS.
You are genuinely hands-on with modern AI-enabled development tools and agentic engineering approaches. This is not “a nice-to-have” skill—we are looking for someone who has already integrated AI into their engineering workflow and can speak from practical experience.
You understand how AI can be incorporated across the software development lifecycle, and you have experimented with or implemented agentic workflows where AI systems assist with or automate multi-step development tasks.
You are able to represent and be accountable for the technical output of your team, either through your own technical depth or through strong collaboration with senior engineers.
You know when to go deep into technical problems and when to empower your team to lead.
You have a strong understanding of scalability and system design, with experience building or guiding systems that support significant growth.
You stay curious about the rapidly evolving AI tooling landscape and can translate new developments into practical improvements for a lean, high-velocity engineering organization.
You are a highly collaborative leader with curiosity, humanity, and generosity.
You invest deeply in the professional development of those around you and communicate complex technical ideas in ways that are accessible to a wide range of stakeholders.
You have well-developed stakeholder management skills, with the ability to build trust, influence decisions, and drive positive outcomes across product, design, and business teams.
You are comfortable operating in environments with ambiguity and shifting priorities, and you bring a proactive, data-informed approach to decision-making even when perfect information is unavailable.
You are energized — not intimidated — by working alongside senior individual contributors who may be more technically specialized than you.
You see your role as amplifying the impact of great engineers, creating conditions where they can do their best work and where teams succeed collectively.

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.

Benefits

Transparent and social culture, challenging work, fast learning cycles, practical training, and meaningful feedback
Strong sense of ownership and strategic work that impacts our product, users, colleagues, business, and world
Competitive salary (plus equity) commensurate with experience a nd location
Tier 1 Geo (SF/NYC): $180k - $210k
Tier 2 Geo: $160k - $190k
Tier 3 Geo: $143k - $170k
Comprehensive benefits package
100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents
Health, commuter, and parking flexible spending accounts
Employee Assistance Program (mental health, financial health, legal support, and more)
Free access to wellbeing apps like Ginger and Headspace
Flexible paid time off and paid holidays
Generous paid parental leave
Short and long-term disability insurance
Annual professional development budget
Company-provided laptop
Remote-first culture
Life insurance (100% company paid)
401(k)