Engineering Director

Role / Department Overview

Pathstream 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. Remote, U.S.

What We Do

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 about 60 employees eager to scale our solution and transform careers across the United States.

The Role

Leadership & Team Management

• Lead, grow, and develop one or more engineering teams – accountable for people management including coaching, performance reviews, compensation, promotions, and when necessary, performance management.
• 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 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.

Strategy & Execution

• 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, resolving conflicting priorities without escalation; lead effectively in environments of uncertainty and ambiguity.
• Define what success looks like by setting clear goals, establishing measurable outcomes, and tracking progress so the impact of your team’s work on customers and the business is always clear.
• Clarify ownership and decision‑making across initiatives, delegating 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.

AI & Agentic Engineering Leadership

• Lead by example in an engineering culture where AI is central; hands‑on with modern AI‑enabled development tools (Claude Code, Cursor, GitHub Copilot, etc.) and regularly explore workflow improvements.
• Drive adoption of agentic engineering workflows across your team(s) where AI systems assist or automate multi‑step engineering tasks; build internal frameworks, playbooks, or reusable patterns to leverage AI safely and effectively.
• Coach engineers on collaborating effectively with AI systems.
• Partner with engineering leadership to shape Pathstream’s evolving AI engineering strategy, evaluate emerging tools, and ensure responsible adoption aligned with internal AI guardrails.
• Stay informed about advancements in AI‑assisted and agentic development; bring practical insights back to the team and continuously raise the bar for speed, quality, and impact.

Cross‑Functional Partnership

• Build strong relationships with stakeholders including product managers, designers, customers, and cross‑functional partners; represent your team’s goals, metrics, and progress 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 prioritize team work to deliver the greatest value.
• Promote strong knowledge‑sharing practices across teams so that no individual — including yourself — is a single point of failure.

Experience & Qualifications

• 7–10 years of professional software engineering experience, including at least 4 years of hands‑on technical work and 3–5 years in engineering leadership with 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, or leading a single team through growth and complexity at a scope where you regularly drove alignment, unblocked cross‑team dependencies, and influenced decisions beyond your immediate org.
• Comfortable independently owning full scope of people‑management responsibilities, including performance management, compensation discussions, career development planning, promotions, and difficult conversations.
• Familiarity with modern web application stacks similar to ours – Ruby on Rails, React, JavaScript, Docker, PostgreSQL, AWS.
• Hands‑on with modern AI‑enabled development tools and agentic engineering approaches; have integrated AI into engineering workflow and can speak from practical experience.
• Understanding of how AI can be incorporated across the software development lifecycle; have experimented with or implemented agentic workflows where AI assists with or automates multi‑step development tasks.
• Strong understanding of scalability and system design, with experience building or guiding systems that support significant growth.
• Curiosity about AI tooling landscape and ability to translate new developments into practical improvements for a lean, high‑velocity engineering organization.
• Highly collaborative leader with curiosity, humanity, and generosity; invest deeply in the professional development of others and communicate complex technical ideas in accessible ways.
• Well‑developed stakeholder management skills, building trust, influencing decisions, and driving positive outcomes across product, design, and business teams.
• Comfortable operating in ambiguous, shifting‑priority environments; proactive, data‑informed approach to decision‑making even with limited information.
• Energetic and not intimidated by working alongside senior individual contributors; see role as amplifying the impact of great engineers and creating conditions for collective success.

What We Offer

• 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 and 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 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).

Commitment to Diversity and Inclusion

Our company values diversity and believes diverse teams make innovation possible. We work on complex, difficult problems with no linear or clear solutions. We need a diverse team that can bring different perspectives and approaches, and whose experiences reflect the full set of stakeholders we seek to serve. As such, Pathstream is an equal‑opportunity employer. We encourage all qualified applicants from any race, color, religion, sex, gender identity, sexual orientation, national origin, disability status, protected veteran status, or other characteristics to apply.

San Francisco Fair Chance Ordinance

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

Work Authorization

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

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