Sr. Staff Software Engineer 

Pathstream  |  Engineering  |  Remote  

ROLE / DEPARTMENT OVERVIEW

Pathstream is seeking an experienced Sr Staff Software Engineer to operate as a senior technical leader on the engineering team, accountable for the most ambiguous, highest-leverage technical work across our platform. This is a hybrid role reporting to the SVP of Engineering: you will operate as a hands-on Sr Staff engineer and as the direct manager of two mid-level engineers.

We are looking for someone who has already built a strong foundation as a senior engineer in one or more critical domains, and who now brings the maturity, range, and ambition to set technical direction across teams — shaping architecture, raising the bar on quality and security, and accelerating the engineers around them, including those they directly manage.

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 technical leader who not only embraces this approach but actively pushes the organization forward in building, evaluating, and deploying AI-enabled development tools and agentic engineering workflows. Both as a hands-on practitioner and as a force-multiplier for engineers across the org.

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 the careers of our customers.

THE ROLE

TECHNICAL LEADERSHIP & ARCHITECTURE

• Set technical direction across multiple domains of Pathstream's platform and shape architecture decisions that span service and team boundaries. Produce the technical documentation that lets your team learn from and execute. 
• Own the most complex, ambiguous, and consequential technical work in your domain end-to-end: greenfield service design, large refactors, new platform capabilities, and unprecedented problems with no clear playbook.
• Anticipate systemic risks across the platform before they surface, scalability ceilings, data-flow brittleness, security posture, cross-service contracts and drive resolution.
• Operate as a credible voice at the engineering org level. Lead roadmap conversations that cross team boundaries, identify and drive resolution of org-level technical risks, and influence how Pathstream's engineering teams build collective technical capability.

EXECUTION & PLATFORM HEALTH

• Set and evolve the bar for quality versus speed in your domain, ensuring alignment with strategic goals and coaching others on making pragmatic trade-offs. Fostering a culture that values effective execution without unnecessary complexity.
• Act as a senior technical authority for security and compliance in your domain. Partner with engineering leadership on SOC2, vulnerability management, threat modeling, and the controls that protect Pathstream's enterprise customers and learners.
• Be deeply involved in code reviews of significant scope and impact. Provide thorough, constructive feedback that raises the quality bar and that helps less experienced engineers grow.
• Be willing and able to jump into incidents well outside your normal scope of work in an emergency. Translate on-call insights and operational pain into new technical priorities and architectural opportunities.

AI & AGENTIC ENGINEERING LEADERSHIP

• Be a hands-on practitioner and force-multiplier for AI-native engineering at Pathstream. You are not just adopting AI-enabled development tools (Claude Code) you are pushing the frontier of how Pathstream uses them.
• Lead the design and adoption of agentic engineering workflows in your domain where AI systems assist with or automate multi-step engineering tasks. Build internal frameworks, skills, MCP servers, evaluation harnesses, and reusable patterns that let engineers leverage AI safely and effectively.
• Partner with engineering leadership to shape Pathstream's evolving AI engineering strategy: evaluate emerging tools, define where AI creates the most leverage, and ensure responsible adoption aligned with internal AI guardrails.
• Coach engineers across the organization on how to collaborate effectively with AI systems. Define what good context engineering looks like, when to use which tool, how to evaluate AI-generated output, and how to know when not to trust it.

PEOPLE LEADERSHIP & TEAM CRAFT

• Directly manage two mid-level engineers. Own their growth and performance end-to-end, regular 1:1s, growth plans, performance reviews, compensation recommendations, and timely candid feedback. 
• Your reports should grow faster because they work with you, through pairing, design feedback, code review, and exposure to the technical decisions you are leading. People management is a force-multiplier on your technical leadership, not a separate track.
• Develop engineers beyond your direct reports. Invest in coaching teammates across the engineering org, through pairing, code review, design feedback, and thoughtful technical critique.
• Build strong relationships with product managers, designers, and cross-functional partners. Represent your team's and your domain's technical perspective clearly in conversations about scope, sequencing, and trade-offs.

ABOUT YOU

EXPERIENCE

• You bring 10+ years of professional software engineering experience, with a strong track record at the senior IC level — typically 3+ years as a Staff or equivalent senior IC, or a Senior IC ready to step into broader scope.
• You have built and shipped systems that other engineers depend on at scale, and you have been the technical owner for a major service, platform area, or greenfield initiative end-to-end.
• You have a proven track record of driving multi-team technical initiatives. Setting architectural direction, unblocking cross-team dependencies, and influencing decisions beyond your immediate team.
• You bring deep familiarity with modern web application stacks similar to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS.
• You bring practical experience with security and compliance work in a SaaS environment including SOC2, vulnerability management, authentication systems, and the day-to-day discipline of operating production systems that hold customer data.
• You have experience mentoring or leading engineers as a tech lead, a senior IC running a working group, or in a formal management capacity. Direct people-management experience is a plus but not required; what is required is genuine interest in growing engineers and the maturity to take on direct reports with thoughtful coaching support from your manager.

AI & TECHNICAL LEADERSHIP

• You are genuinely hands-on with modern AI-enabled development tools and agentic engineering approaches. We are looking for someone who has already integrated AI deeply into their engineering workflow and can speak from practical experience about what works, what doesn't, and why.
• You have built or meaningfully contributed to agentic workflows: MCP servers, skills, evaluation harnesses, multi-step automations, or AI-assisted development pipelines where AI orchestrates work rather than just assisting with individual tasks.
• You can architect and ship AI features in production systems, designing systems where AI is a first-class component (LLM orchestration, evaluation, observability, cost management).
• You have a strong understanding of scalability and system design, with experience building or guiding systems through significant growth in scale, complexity, or scope of ownership.

LEADERSHIP & COLLABORATION

• You lead through influence rather than authority. You are sought out for technical feedback because of your thorough, helpful advice and your kind, respectful communication.
• You communicate complex technical ideas in ways that are accessible to a wide range of stakeholders. You write crisp narratives that create understanding, influence decisions, and unblock 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 bring curiosity, humanity, and generosity to your work. You invest deeply in the engineers around you, celebrate the wins of others, and treat disagreement as a collaboration tool rather than a contest to win.
• You are excited by the hybrid nature of this role. You want to stay deep in the technical work while taking on direct people responsibility, and you see managing two engineers as a 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
• Salary and total compensation offerings are contingent upon the candidate's level of expertise and geographic location, ensuring equitable remuneration.
• Tier 1: $204K-$226K (NYC metro & San Francisco)
• Tier 2: $184K-$203K
• Tier 3: $163K-180K

Comprehensive benefits package:

• 100% employer-paid medical, dental, and vision for you; 50% for partner/spouse and dependents
• Health, commuter, and parking flexible spending accounts
• Employee Assistance Program (mental health, financial health, legal support)
• Free access to wellbeing apps (Ginger, 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. 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.

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.