[Remote] Sr. Staff Software Engineer

Note: The job is a remote job and is open to candidates in USA. 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. The role involves setting technical direction, managing mid-level engineers, and advancing AI-native engineering practices within the organization.

Responsibilities

• 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
• 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
• 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
• 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

Skills

• 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
• Built and shipped systems that other engineers depend on at scale, and have been the technical owner for a major service, platform area, or greenfield initiative end-to-end
• Proven track record of driving multi-team technical initiatives. Setting architectural direction, unblocking cross-team dependencies, and influencing decisions beyond your immediate team
• Deep familiarity with modern web application stacks similar to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS
• 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
• 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
• Genuinely hands-on with modern AI-enabled development tools and agentic engineering approaches. Integrated AI deeply into their engineering workflow and can speak from practical experience about what works, what doesn't, and why
• 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
• Can architect and ship AI features in production systems, designing systems where AI is a first-class component (LLM orchestration, evaluation, observability, cost management)
• Strong understanding of scalability and system design, with experience building or guiding systems through significant growth in scale, complexity, or scope of ownership
• Lead through influence rather than authority. Sought out for technical feedback because of thorough, helpful advice and kind, respectful communication
• Communicate complex technical ideas in ways that are accessible to a wide range of stakeholders. Write crisp narratives that create understanding, influence decisions, and unblock teams
• Comfortable operating in environments with ambiguity and shifting priorities, and bring a proactive, data-informed approach to decision-making even when perfect information is unavailable
• Bring curiosity, humanity, and generosity to work. 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
• Excited by the hybrid nature of this role. Want to stay deep in the technical work while taking on direct people responsibility, and see managing two engineers as a way to multiply impact

Benefits

• 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)

Company Overview