Director Engineering Operations (Chief of Staff)

We are seeking a strategic operator to serve as the force multiplier for our CTO and Engineering Leadership Team. Our 800-person SaaS organization has reached a pivotal scale, product-market fit is strong, velocity is high, and our next stage of growth depends on maturing our internal engine. This role sits at the intersection of strategy, data, delivery, and culture, ensuring that Engineering operates with clarity, efficiency, and alignment. The Director of Engineering Operations will architect the operational rhythm of the Engineering organization, elevate decision quality through data, drive cross-functional initiatives, and build the systems that enable predictable, high-quality delivery at scale. This is a highly visible, career-accelerating role for a leader who thrives at the point where people, process, and technology meet. Key Responsibilities Operational Mechanics & Rhythm of Business (RoB) · Architect and own the Engineering operating cadence, including QBRs, Monthly Business Reviews, strategic planning sessions, and org-wide communications. · Drive fiscal and resource governance, partnering with Finance and HR on budgeting, headcount planning, workforce strategy, and cloud cost optimization (FinOps). · Act as the communication conduit for the CTO—drafting strategic memos, board-facing narratives, and alignment messages for 400+ engineers. Engineering Intelligence, Metrics & Insights · Define Engineering “success” metrics, moving beyond vanity KPIs to track velocity, quality, efficiency, and people health (e.g, capital allocation, retention, eNPS). · Own the Engineering Performance Dashboard, synthesizing complex data sets into clear, actionable insights for senior leadership. · Lead data-driven interventions, proactively identifying bottlenecks, risks, or delivery challenges and recommending solutions. Delivery Assurance & Portfolio Management · Maintain a portfolio-level view of all major engineering initiatives, serving as the CTO’s early warning system for slippage, dependency risks, and scope creep. · Standardize delivery frameworks—create lightweight yet high-compliance definitions of "Ready" and "Done" to drive consistent execution across teams. · Oversee major cross-functional programs, ensuring alignment on scope, priorities, and timelines. Tools, Systems & Workflow Optimization · Optimize engineering tooling, workflows, and automation, driving adoption of systems (Jira, Confluence, GitHub, CI/CD) that increase velocity and output quality. · Partner with Engineering and Product to evaluate and implement AI-driven tools and practices that improve productivity, automation, and decision-making. · Establish training, communication, and safe-use guidelines for responsible and effective AI integration. Horizontal Initiatives & Cross-Functional Leadership · Serve as the cross-functional glue between Engineering, Product, Design, QA, Customer Success, and other partners. · Lead complex, horizontal initiatives such as GRC framework implementations, cloud migrations, or GenAI adoption programs. · Act as a change agent, driving organizational adoption of new processes, structures, and operating models. Engineering Business Operations · Manage operational budgets, vendor relationships, and resource planning. · Partner with Finance, Talent Acquisition, and HR on hiring priorities, onboarding, and retention efforts. · Prepare operational dashboards and reporting for executive leadership and the Board. Leadership & Culture · Mentor and develop Engineering Operations and Program Management staff. · Foster a culture of accountability, continuous improvement, operational rigor, and data-driven decision making. · Strengthen clarity, communication, and alignment across the Engineering org. · Demonstrate diplomatic authority, the ability to influence without formal power, hold senior leaders (including VPs of Engineering) accountable to commitments, and preserve strong, trust-based relationship. Required Experience/Skills · 8–1