Sr. Staff Software Engineer

Sr. Staff Software Engineer Keystone AI | Engineering | Remote ROLE / DEPARTMENT OVERVIEW Keystone AI 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 Keystone AI 's AI-native engineering practices. AI adoption is already deeply embedded in how we build software at Keystone AI . 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 Keystone AI 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 Keystone AI '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 Keystone AI '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 Keystone AI '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 Keystone AI . You are not just adopting AI-enabled development tools (Claude Code) you are pushing the frontier of how Keystone AI 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 Keystone AI '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 CRAF