Sr. Staff Software Engineer

Role overview This hybrid role combines senior staff-level technical leadership with direct people management of two mid-level engineers on a remote-first engineering team focused on workforce learning technology. The engineer will own the most ambiguous, high-leverage technical problems across the platform, set architectural direction that spans team boundaries, and actively push the organization's adoption of AI-native and agentic engineering workflows. It is a force-multiplier position: hands-on coding on hard problems paired with raising the bar for quality, security, and engineering velocity organization-wide.

Responsibilities - Set technical direction across multiple platform domains, drive architecture decisions across team boundaries, and produce the documentation that enables execution. - Own the most complex, ambiguous technical work end to end, including greenfield service design, large refactors, and new platform capabilities. - Anticipate systemic risks around scalability, data integrity, security, and cross-service contracts, and drive resolution before they surface. - Serve as a senior authority for security and compliance, partnering with leadership on SOC2, vulnerability management, threat modeling, and production operations. - Lead the design and rollout of AI-enabled development tools and agentic engineering workflows, both as a hands-on practitioner and as a cross-org multiplier. - Manage and develop two direct reports through regular 1:1s, growth planning, performance reviews, and pairing on hard problems.

Requirements - 10+ years of professional software engineering experience, including 3+ years at Staff or equivalent senior IC scope. - Hands-on familiarity with modern web stacks: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS. - Practical experience with SaaS security and compliance work, including SOC2, vulnerability management, authentication, and production operations. - Track record of driving multi-team technical initiatives, setting architectural direction, and unblocking cross-team dependencies. - Experience mentoring engineers as a tech lead, working group lead, or formal manager, with genuine interest in growing people. - Strong written and verbal communication, able to translate complex technical ideas for diverse stakeholders.

Nice to have - Direct people-management experience. - Comfort operating in environments with shifting priorities and making data-informed decisions with imperfect information.

Benefits and work setup - Remote-first culture within the US; visa sponsorship is not available. - Tiered salary bands by location: Tier 1 $225K-$270K (NYC metro & San Francisco), Tier 2 $205K-$250K, Tier 3 $180K-$220K. - 100% employer-paid medical, dental, and vision for employees; 50% for spouse/partner and dependents. - Health, commuter, and parking FSAs; EAP; free access to mental wellness apps. - Flexible paid time off, paid holidays, generous paid parental leave, and short/long-term disability. - Life insurance, 401(k), annual professional development budget, and a company-provided laptop.