Director, Engineering Operations

This is a fully remote position, open to applicants in California, +4 more states.

📋 Description

• Design, implement, and continually refine the operating cadence of the CTO organization, encompassing quarterly business reviews, initiative and program assessments, goal-setting cycles, leadership forums, and internal communications.

• Develop reusable standards for agendas, pre-reads, synthesis, status updates, risk and confidence language, ownership, dependencies, decision documentation, and follow-through.

• Transform fragmented execution signals into clear, decision-ready narratives for the CTO and Engineering leadership.

• Ensure that forums facilitate decisions and trade-offs rather than merely providing status updates.

• Enhance visibility of Engineering priorities, commitments, dependencies, and risks throughout the organization.

• Strengthen early risk detection and escalation processes.

• Utilize data and qualitative insights to differentiate genuine progress from mere activity or optimism.

• Collaborate with the CTO, Engineering leaders, Finance, People, Product, and other departments to align strategy, priorities, capacity, headcount, funding, and operational norms.

• Aid in workforce and headcount planning, financial and investment alignment, and organizational planning through analysis and decision-support materials.

• Improve operational norms across geographies and functions.

• Provide structure to ambiguous, cross-cutting, or high-risk initiatives lacking a defined program home.

• Support major transformations, IPO readiness, M&A diligence, and other CTO-level projects.

• Assess when to remain involved, escalate issues, or withdraw from strategic initiatives.

• Institutionalize sound judgment into reusable systems, templates, and standards.

• Leverage automation, analytics, and AI-assisted workflows to enhance signal quality and operational efficiency.

• Communicate changes effectively and foster adoption through clarity, utility, and trust.

• Design and implement AI initiatives that integrate AI into software development lifecycles, CI/CD pipelines, and cloud operations.

• Establish frameworks and benchmarks for the adoption, effectiveness, and impact of AI tools.

• Lead programs focused on automated observability, AI-driven incident management, and intelligent optimization of cloud resources.

⛳️ Requirements

• Strong technical expertise in software engineering, distributed systems, or cloud infrastructure operations.

• Proven experience in a strategic leadership or business operations capacity.

• Capability to convert ambiguous, cross-functional challenges into clear decisions, accountability, operating mechanisms, and measurable outcomes.

• Proficient in designing and managing operating cadences, business reviews, planning processes, leadership forums, or similar frameworks.

• Ability to influence without direct authority and establish trust across various geographies, functions, and organizational strata.

• Comfort in fast-paced environments with incomplete information and competing priorities.

• Experience in supporting a CTO, VP of Engineering, or a comparable technology executive in a rapidly growing or transformative setting.

• Familiarity with annual planning, portfolio management, headcount planning, financial modeling, or investment evaluations.

• Background in supporting IPO readiness, M&A diligence, organizational transformation, or other enterprise-scale changes.

• Experience in creating operating standards, metrics, dashboards, or lightweight automation solutions.

• Practical experience in designing or deploying AI tools, LLM integrations, AI-assisted coding, or automated operations platforms within large-scale engineering or cloud environments.

• Successful completion of a background check.

• Legal eligibility to work in the country where the position is based.

🏝️ Benefits

• Competitive salaries and equity grants.

• Unlimited vacation time.

• Health, dental, and vision coverage.

• 401K plan.

• Flexible Spending Account (FSA).

• Commuter benefits.

• Regular team celebrations and recreational events.

• Home internet and phone stipend.

• Opportunities for learning and development.

• Ability to influence a high-performance company on its path to IPO.

• Comprehensive health and wellness benefits.

• Discretionary bonuses.

• Stock options.