Engineering Manager

Engineering Manager Pathstream | Engineering | Remote ROLE / DEPARTMENT OVERVIEW Pathstream is seeking an Engineering Manager to lead one of our engineering pods, a team of 4+ engineers building and maintaining the platform that powers our learning and workforce-development products. This is a people management role reporting to the SVP of Engineering: you will own the growth, performance, and effectiveness of your team, while staying technical enough to set direction within your domain, drive delivery of broadly scoped initiatives, and hold a high bar on quality. We are looking for someone who has built a strong foundation as an engineer, highly proficient in one or more technical areas, and is now energized by multiplying their impact through others. Growing the engineers on their team, owning their team's roadmap, and turning company strategy into well-sequenced, well-executed engineering work. A core expectation of this role is to champion Pathstream's AI-native engineering practices within your team. AI adoption is already deeply embedded in how we build software at Pathstream. We are looking for a manager who actively drives the effective and responsible adoption of AI-enabled development tools on their team, and who coaches engineers to get real leverage from them. 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 ~60 employees eager to scale our solution and transform careers across the United States. THE ROLE PEOPLE LEADERSHIP & TEAM CRAFT Directly manage a team of 4+ engineers. Own their growth and performance end-to-end — regular 1:1s, growth plans, performance reviews, compensation recommendations, and timely, candid feedback. Run performance cycles in partnership with your manager, navigating the most sensitive situations with support from senior leadership. Own hiring for your team. Partner with recruiting to scope roles, run interview loops, and play a central role in evaluating engineering candidates and shaping hiring decisions. Build a team with clear roles, healthy collaboration patterns, and strong engagement, and take ownership of improving the experience of more junior members of the team. Deliver feedback proactively and partner on solutions. Offer timely, unprompted feedback that integrates new context as it emerges, co-create next steps with the recipient, and know when escalation is appropriate. Develop engineering talent. Demonstrate success in growing engineers, and establish formal mentoring relationships with more junior engineers — through pairing, design feedback, and code review. Be a steadying force and a positive influence. Provide team stability through priority and business shifts, bring everyone into the conversation, advocate for the growth and success of others, and publicly celebrate the achievements of your teammates. TECHNICAL DIRECTION & EXECUTION Define and own your team's roadmap and technical direction. Influence team priorities to match business objectives, lead service-level planning and technical strategy discussions, and translate company strategy into sequenced, well-scoped engineering work. Own planning and prioritization for large initiatives. In partnership with leadership, estimate and manage timelines and risk, define success criteria, bring teammates along throughout the planning process, and sequence work so it can be spread efficiently across multiple people. Guide your team through ambiguous, broadly scoped work — major refactors, new services, and other impactful changes — driving end-to-end resolution of complex problems by drawing on both established and new techniques. Maintain strong technical proficiency. Stay highly proficient in one or more technical areas and effective across a wide range, with a deep enough understanding of your team's systems to contribute across its entire domain of ownership. Take ownership of transferring knowledge to less-experienced teammates to support scalability and reduce single points of failure. Hold a high quality bar. Identify where code structure and architecture can be improved for testability and maintainability and bring well-formed proposals to the team. Provide thorough, constructive code review that goes beyond functionality to how code should be structured for future reliability and maintainability. Make pragmatic trade-offs. Make sound, informed decisions about technical debt and velocity, and proactively call out when a plan must change mid-project, recommending a new approach based on current priorities. Ensure technical documentation accounts for stability, performance, scalability, and business needs, and review your team's documents constructively without being nitpicky. AI & AGENTIC ENGINEERING LEADERSHIP Champion AI-native engineering on your team. Ensure your engineers are adopting AI-enabled development tools (Claude Code) effectively and responsibly, in line with Pathstream's internal AI guardrails. Coach your team on how to collaborate well with AI systems, when to use which tool, and how to evaluate AI-generated output. Embrace change introduced by evolving technology. Partner with engineering leadership to roll out and refine AI tooling, workflows, and standards across the org, and help your team turn new capabilities into real, measurable leverage. Stay hands-on enough to be credible. You use these tools in your own work and can speak from practical experience about what works, what doesn't, and why. PLATFORM HEALTH, SECURITY & OPERATIONS Ensure your team operates production systems well. Participate in on-call, including, with support, code outside your team's normal responsibility and use observability tooling to catch issues before they affect customers. Partner with engineering leadership on security and compliance in your domain, including SOC2, vulnerability management, authentication systems, and the controls that protect Pathstream's enterprise customers and learners. Translate operational pain and on-call insights into roadmap priorities and process improvements, and ensure your team maintains sound DevOps and operational practices across infrastructure, APIs, automation, and deployment pipelines. ABOUT YOU EXPERIENCE You bring 4+ years of professional software engineering experience and are highly proficient in one or more technical areas, with the range to be effective across many others. You have 2+ years leading and mentoring engineers — as a team lead, technical lead, or engineering manager — and a demonstrated track record of developing engineering talent. You have owned the technical design and delivery of broadly scoped work end-to-end — a major refactor, a new service, or a comparably impactful initiative — and been independently responsible for the full delivery process in your area. You bring a deep understanding of scalability best practices and experience designing and implementing solutions that can handle significant growth. You bring familiarity with modern web application stacks similar to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS. You understand infrastructure automation, platform security, and DevOps practices, and you are comfortable with the discipline of operating production systems that hold customer data. Practical experience with security and compliance in a SaaS environment (SOC2, vulnerability management, authentication) is a plus. AI & TECHNICAL LEADERSHIP You are hands-on with modern AI-enabled development tools and agentic engineering approaches and bring genuine enthusiasm and the drive to grow production experience with them quickly. You embrace change introduced by evolving technology, set ambitious goals, and proactively seek feedback on your own areas of growth. You have practical judgment about when AI accelerates engineering work and when it introduces risk, and you can articulate that distinction to your team. LEADERSHIP & COLLABORATION You lead through influence and trust rather than authority. You are sought out for technical and people feedback because of your thorough, helpful advice and your kind, respectful communication. You communicate with clarity, brevity, and focus, and you are effective in crucial conversations even when they are uncomfortable. You can translate technical concepts into language that is understood and useful across teams, adapting your message for different audiences. You drive discussions with product and other stakeholders that turn ambiguous problem statements into clear engineering requirements, and you work productively through challenging conversations when constraints conflict. 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 bring others along rather than working in a silo. You are a steadying force for your team, you invest deeply in the engineers around you, you celebrate the wins of others, and you treat disagreement as a collaboration tool rather than a contest to win. You see managing a team as the way to multiply your impact. 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 commensurate with experience and geographic location: Tier 1: $160K–$183K (NYC metro & San Francisco) Tier 2: $144K–$165K Tier 3: $128K–$146K Comprehensive benefits package 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents Flexible spending account (health) 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 13 paid holidays Generous paid parental leave Short and long-term disability insurance (100% company paid) Annual professional development budget Company-provided laptop Remote-first culture Life insurance (100% company paid) Optional supplemental life insurance 401(k) Discounted pet insurance 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. #LI-Remote