[Remote] Director Engineering Operations (Chief of Staff)

Note: The job is a remote job and is open to candidates in USA. Diligent is an AI leader in governance, risk and compliance SaaS solutions, seeking a strategic operator to enhance their Engineering leadership. The Director of Engineering Operations will architect operational rhythms, elevate decision quality through data, and drive initiatives to ensure effective and efficient engineering processes.

Responsibilities

• 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
• 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

Skills

• 8–10+ years in Engineering Operations, Technical Program Management, Strategy/Business Operations, or Software Engineering leadership within a high-growth SaaS environment
• Strong understanding of SDLC, agile methodologies, CI/CD, DevOps, and microservices architecture
• Advanced analytical skills with expertise in Excel, Looker, Tableau, or similar tools—able to convert data into executive-ready narratives
• Demonstrated experience driving AI-related innovation across engineering teams, including evaluating AI opportunities, implementing tools, and influencing change at scale
• Exceptional communication and stakeholder management skills; ability to influence without authority and build trust across all levels
• Demonstrated success improving engineering processes, delivery predictability, and cross-functional alignment at scale
• Experience defining operational frameworks, delivery standards, and KPI systems within a Global Organization
• Experience with OKR frameworks
• People leadership
• Certifications (PMP, Agile, Lean)

Benefits

• Flexible work environment
• Global days of service
• Comprehensive health benefits
• Meeting free days
• Generous time off policy
• Wellness programs
• Hybrid work model
• Work onsite at least 50% of the time if within a commuting distance to one of our Diligent office locations

Company Overview

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