Diligent · 1 month ago
Director Engineering Operations (Chief of Staff)
United States
Full-time
Remote
Director/Executive
$174K/yr - $220K/yr
8+ years expDiligent 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.
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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
Qualification
Required
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
Preferred
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
Diligent
Diligent is the largest GRC SaaS provider, with 1M users, across 23,000 organizations, valued at $7B+ and $500 million+ in revenue.
1001-5000 employees
H1B Sponsorship
Diligent has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Engineering and Development
Trends of Total Sponsorships
*2021 (1)
Funding
Current Stage
Public CompanyTotal Funding
$30MKey Investors
Clearlake Capital GroupAccel,Matrix
2020-08-05Private Equity
2018-02-09Corporate Round
2016-02-16Acquired
Leadership Team
Michael Flickman
Executive Vice President and Chief Technology Officer
D
David Adkins
Vice President, Customer Success
Recent News
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