Diligent

Chief of Staff

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• Mentor and develop Engineering Operations and Program Management staff.
• Foster a culture of accountability, continuous improvement, operational rigor, and data-driven decision making.

Director, Engineering Operations – Chief of Staff