[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.ResponsibilitiesArchitect and own the Engineering operating cadence, including QBRs, Monthly Business Reviews, strategic planning sessions, and org-wide communicationsDrive 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+ engineersDefine 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 leadershipLead data-driven interventions, proactively identifying bottlenecks, risks, or delivery challenges and recommending solutionsMaintain a portfolio-level view of all major engineering initiatives, serving as the CTO’s early warning system for slippage, dependency risks, and scope creepStandardize delivery frameworks—create lightweight yet high-compliance definitions of 'Ready' and 'Done' to drive consistent execution across teamsOversee major cross-functional programs, ensuring alignment on scope, priorities, and timelinesOptimize engineering tooling, workflows, and automation, driving adoption of systems (Jira, Confluence, GitHub, CI/CD) that increase velocity and output qualityPartner with Engineering and Product to evaluate and implement AI-driven tools and practices that improve productivity, automation, and decision-makingEstablish training, communication, and safe-use guidelines for responsible and effective AI integrationServe as the cross-functional glue between Engineering, Product, Design, QA, Customer Success, and other partnersLead complex, horizontal initiatives such as GRC framework implementations, cloud migrations, or GenAI adoption programsAct as a change agent, driving organizational adoption of new processes, structures, and operating modelsManage operational budgets, vendor relationships, and resource planningPartner with Finance, Talent Acquisition, and HR on hiring priorities, onboarding, and retention effortsPrepare operational dashboards and reporting for executive leadership and the BoardMentor and develop Engineering Operations and Program Management staffFoster a culture of accountability, continuous improvement, operational rigor, and data-driven decision makingStrengthen clarity, communication, and alignment across the Engineering orgDemonstrate diplomatic authority, the ability to influence without formal power, hold senior leaders (including VPs of Engineering) accountable to commitments, and preserve strong, trust-based relationshipSkills8–10+ years in Engineering Operations, Technical Program Management, Strategy/Business Operations, or Software Engineering leadership within a high-growth SaaS environmentStrong understanding of SDLC, agile methodologies, CI/CD, DevOps, and microservices architectureAdvanced analytical skills with expertise in Excel, Looker, Tableau, or similar tools—able to convert data into executive-ready narrativesDemonstrated experience driving AI-related innovation across engineering teams, including evaluating AI opportunities, implementing tools, and influencing change at scaleExceptional communication and stakeholder management skills; ability to influence without authority and build trust across all levelsDemonstrated success improving engineering processes, delivery predictability, and cross-functional alignment at scaleExperience defining operational frameworks, delivery standards, and KPI systems within a Global OrganizationExperience with OKR frameworksPeople leadershipCertifications (PMP, Agile, Lean)BenefitsFlexible work environmentGlobal days of serviceComprehensive health benefitsMeeting free daysGenerous time off policyWellness programsHybrid work modelWork onsite at least 50% of the time if within a commuting distance to one of our Diligent office locationsCompany OverviewDiligent is the largest GRC SaaS provider, with 1M users, across 23,000 organizations, valued at $7B+ and $500 million+ in revenue. It was founded in 2001, and is headquartered in New York, New York, USA, with a workforce of 1001-5000 employees. Its website is http://diligent.com.Company H1B SponsorshipDiligent has a track record of offering H1B sponsorships, with 1 in 2021. Please note that this does not guarantee sponsorship for this specific role.