Senior Staff Software Engineer

This is a fully remote position, open to applicants in United States.

📋 Description

• Establish the technical vision across various domains of Pathstream's platform and influence architecture decisions that extend beyond individual services and teams. Create comprehensive technical documentation to facilitate team learning and execution.

• Take ownership of the most challenging, uncertain, and impactful technical projects in your area from start to finish: designing new services, executing large refactors, developing new platform features, and tackling unprecedented challenges without established guidelines.

• Proactively identify systemic risks throughout the platform before they become apparent, including scalability limits, data-flow vulnerabilities, security measures, and cross-service agreements, while driving their resolution.

• Serve as a credible leader within the engineering organization. Facilitate roadmap discussions that span multiple teams, pinpoint and resolve organization-wide technical risks, and shape how Pathstream's engineering teams enhance their collective technical capabilities.

• Define and elevate the standards for quality versus speed in your domain, aligning with strategic objectives and mentoring others on making practical trade-offs. Cultivate a culture that prioritizes effective execution while minimizing unnecessary complexity.

• Act as a senior technical authority on security and compliance within your area. Collaborate with engineering leadership on SOC2 compliance, vulnerability management, threat assessment, and the controls safeguarding Pathstream's enterprise customers and learners.

• Engage actively in code reviews of substantial scope and significance. Provide detailed, constructive feedback that raises quality standards and aids in the development of less experienced engineers.

• Be prepared to address incidents well outside your usual responsibilities in emergencies. Transform insights gained from on-call experiences and operational challenges into new technical priorities and architectural possibilities.

• Be an active practitioner and catalyst for AI-native engineering at Pathstream. You will not only utilize AI-enabled development tools (such as Claude Code) but also advance the boundaries of their application within the organization.

• Lead the design and implementation of intelligent engineering workflows in your domain, where AI systems assist with or automate complex engineering tasks. Develop internal frameworks, skills, MCP servers, evaluation harnesses, and reusable patterns that enable engineers to leverage AI safely and effectively.

• Collaborate with engineering leadership to shape Pathstream's evolving AI engineering strategy: assess emerging tools, identify where AI offers the greatest leverage, and ensure responsible adoption in line with internal AI guidelines.

• Mentor engineers across the organization on effective collaboration with AI systems. Define best practices for context engineering, tool selection, evaluating AI-generated outputs, and recognizing when not to trust them.

• Directly manage two mid-level engineers. Oversee their growth and performance comprehensively, including regular 1:1 meetings, growth plans, performance evaluations, compensation recommendations, and timely, candid feedback.

• Ensure that your reports accelerate their development through collaboration, design feedback, code reviews, and exposure to the technical decisions you are spearheading. People management should enhance your technical leadership, rather than existing as a separate pathway.

• Foster the development of engineers beyond your direct reports. Invest in mentoring colleagues throughout the engineering organization via pairing, code reviews, design feedback, and thoughtful technical critiques.

• Build strong partnerships with product managers, designers, and cross-functional collaborators. Clearly articulate your team's and domain's technical perspectives during discussions regarding scope, sequencing, and trade-offs.

⛳️ Requirements

• You possess over 10 years of professional software engineering experience, showcasing a robust track record at the senior individual contributor level — typically 3+ years as a Staff or equivalent senior IC, or a Senior IC ready to expand their scope.

• You have successfully built and launched systems that other engineers rely on at scale, having been the technical owner for a significant service, platform area, or greenfield project from inception to completion.

• You have a demonstrated history of leading multi-team technical initiatives, establishing architectural direction, removing cross-team dependencies, and influencing decisions beyond your immediate team.

• You have extensive knowledge of modern web application stacks akin to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS.

• You possess hands-on experience with security and compliance activities in a SaaS environment, including SOC2 compliance, vulnerability management, authentication systems, and the routine discipline of operating production systems that handle customer data.

• You have experience mentoring or leading engineers as a tech lead, a senior IC managing a working group, or in a formal management role. Direct people-management experience is advantageous but not mandatory; what is essential is a genuine interest in nurturing engineers and the maturity to manage direct reports with thoughtful coaching support from your manager.

• You are genuinely engaged with modern AI-enabled development tools and intelligent engineering methodologies. We seek someone who has already integrated AI thoroughly into their engineering practices and can share practical insights about what is effective, what isn't, and why.

• You have created or significantly contributed to intelligent workflows: MCP servers, skills, evaluation harnesses, multi-step automations, or AI-assisted development pipelines where AI orchestrates work instead of merely assisting with individual tasks.

• You are capable of architecting and deploying AI features in production systems, designing solutions where AI is an integral component (LLM orchestration, evaluation, observability, cost management).

• You have a solid understanding of scalability and system design, with experience in building or guiding systems through substantial growth in scale, complexity, or scope of ownership.

🏝️ Benefits

• 100% employer-covered medical, dental, and vision insurance for you; 50% coverage for your partner/spouse and dependents.

• Health, commuter, and parking flexible spending accounts.

• Employee Assistance Program (support for mental health, financial wellbeing, and legal issues).

• Complimentary access to wellbeing applications (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 work culture.

• Life insurance fully paid by the company.

• 401(k) plan.