Director Engineering Operations (Chief of Staff)

Director of Engineering Operations

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

· 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

· 8–10+ 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, or certifications (PMP, Agile, Lean).

This is a rare opportunity to operate at the right hand of the CTO and influence how a large-scale technology organization is steered. You'll gain exposure to executive decision-making, board-level communication, and enterprise-wide strategic architecture.

U.S pay range $174,000 —$220,000 USD

About Us

Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster.

At Diligent, we're building the future with people who think boldly and move fast. Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking. Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity. The future belongs to those who keep learning, and we are building it together. At Diligent, you're not just building the future - you're an agent of positive change, joining a global community on a mission to make an impact.

What Diligent Offers You

• Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients
• We care about our people. Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few
• We have teams all over the world. We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.
• Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.

Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place.

Headquartered in New York, Diligent has offices in Washington D.C., London, Galway, Budapest, Vancouver, Bengaluru, Munich, Singapore and Sydney. To foster strong collaboration and connection, this role will follow a hybrid work model. If you are within a commuting distance to one of our Diligent office locations, you will be expected to work onsite at least 50% of the time. We believe that in-person engagement helps drive innovation, teamwork, and a strong sense of community.

We are a drug free workplace. Diligent is proud to be an equal opportunity employer. We do not discriminate based on race, color, religious creed, sex, national origin, ancestry, citizenship status, pregnancy, childbirth, physical disability, mental disability, age, military status, protected veteran status, marital status, registered domestic partner or civil union status, gender (including sex stereotyping and gender identity or expression), medical condition (including, but not limited to, cancer related or HIV/AIDS related), genetic information, or sexual orientation in accordance with applicable federal, state and local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. See also Diligent's EEO