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Director Engineering Operations (Chief of Staff)
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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 (RoB)
· 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.
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.
Learn more at diligent.com or follow us on LinkedIn and Facebook
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 Policy and Know Your Rights. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at recruitment@diligent.com.
To all recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes.
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Assistant Account Executive, Analytics - Political Cycle 2026
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What matters to you? Do you want a job that lets you fight for those things?
Good jobs let you apply your skills. Great jobs feed your sense of purpose.
The thing that defines GMMB isn't what we do—it's our why. We want to make a difference in the world. And we're pretty good at doing good.
Come join the sharp, passionate people at GMMB who bring deep expertise on the issues we care about, from education, health, and climate, to democracy, economic mobility, and social justice. We work with candidates and organizations committed to what matters, because change doesn't just happen on election day. It happens every day.
- GMMB has a hybrid work schedule with at least three days in office presence; additional in office days as needed.
- This position is based in Washington, DC.
- Salary range - $50,000 - $60,000
- This is a full-time, salaried and benefits eligible position to run through mid-November 2026.
This is an entry-level position on GMMB’s award-winning political team and is a great opportunity to play a key supporting role on some of the biggest races and issues in the 2026 midterm election cycle.
As an Assistant Account Executive, Analytics on the Political Team, you would…
- Build, maintain, troubleshoot, and improve GMMB’s industry-leading competitive tracking dashboards in Google Sheets, using advanced formulas and multi-sheet workflows to monitor spending and creative across paid media channels in races across the country.
- Conduct quality assurance and data validation across competitive tracking tools and reports, ensuring the accuracy, consistency, and usability of campaign metrics and client-facing outputs.
- Design and improve spreadsheet-based systems that automate recurring tasks, reduce manual work, and increase team efficiency.
- Draft client-ready summaries of new spending, creative, and competitive trends for races across the country.
- Develop and maintain client and project documents, including timelines/calendars, budget trackers, meeting notes, and conference call reports.
- Research, analyze, and summarize the political landscape and trends for prospective and current clients.
- Draft quick-turn memos and briefs on emerging issues in the political and media landscape.
- Schedule and coordinate client, internal, and vendor meetings and video calls.
- Become well-versed in assigned clients, their priorities, and issue areas, including the political landscape, the state of competitive races, and key news developments that may affect their work.
You have…
- A bachelor's degree from a four-year college or university, or equivalent experience.
- Passion for Democratic politics and advocacy.
- Proficiency in Google Sheets and/or Excel, including pivot tables, VLOOKUP, SUMIFS, FILTER, QUERY, IMPORTRANGE, ARRAYFORMULA, INDIRECT, conditional formatting, and data validation.
- Experience conducting quality assurance, validating data accuracy, and identifying and resolving spreadsheet errors and inconsistencies.
- A strong work ethic, attention to detail, and willingness to work long hours under tight deadlines in high-pressure situations.
- A positive attitude and are a team player!
Preferably but not required, you have…
- Internship or professional experience in political campaigns, issue advocacy, advertising, communications, public relations, or related field.
- Experience with statistics, data visualization, or building and optimizing complex multi-sheet workflows or data models.
- Familiarity with AI tools and sound judgment about how and when to use them to improve efficiency, support research, and troubleshoot or build formulas.
- Experience with data tools such as Civis Analytics, Tableau, Looker, or Power BI.
GMMB is an Equal Opportunity Employer and Prohibits Discrimination and Harassment of Any Kind: GMMB is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at GMMB are based on business needs, job requirements and individual qualifications, without regard to race, age, sex, national origin, ethnicity, mental or physical disability, religion, color, sexual orientation, gender identity and/or expression or military status or other categories defined by applicable local, state and federal statutes in the locations where we operate. GMMB encourages applicants of all ages. GMMB will not tolerate discrimination or harassment based on any of these characteristics.
GMMB values the importance of inclusion and impact. Our success depends on fostering a truly inclusive culture where everyone is welcomed, and where their talents and ideas are channeled into our work. While providing this information is strictly voluntary, we encourage all applicants to provide demographic information. This information, as stated in our EEO statement, will not be used to make employment related decisions. This information will only be shared with qualified and limited personnel who build policies and programs that help make GMMB an inclusive firm.
If you have any questions about the information collected, how it is used and/or have suggestions please reach out to Talent and Culture info@gmmb.com
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Apply to GMMB