Director, Software Engineering

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 This role bridges infrastructure and product engineering: you'll build genuine partnerships across product, AI, and enterprise teams so that ownership is shared and velocity is never blocked by platform constraints. As Director, you'll set a forward-looking cloud vision, proactively align with stakeholders across the business, and ensure the platform scales for multi-shard, multi-region growth while meeting security and compliance commitments (SOC 2, business continuity/disaster recovery, and enterprise security frameworks). The Role: - Cost Efficiency: Drive significant annual infrastructure savings by migrating data workloads to EKS and self-hosting key services such as OpenSearch. - Ingress Convergence: Deprecate legacy frontend ALBs and consolidate to a single EKS-managed ALB per shard, unblocking faster deployments across the org. - Coverage & Bench Depth: Eliminate single points of ownership across Networking, OpenSearch, and Terraform through cross-training and targeted hiring into coverage gaps. - Stakeholder Alignment: Stand up a recurring alignment cadence with Product, AI, Enterprise, and Security so infra planning is driven by demand, not ad-hoc interrupts. - Automation: Ship automated shard buildout via Backstage to remove manual toil from enterprise scaling. - Reliability: Cut P0/P1 incidents attributed to Cloud Platform (DNS, ALB misconfiguration) through hardened ingress patterns and Terraform-policy guardrails, including blocking unauthenticated public endpoints. - Roadmap Ownership: Deliver a roadmap covering Agent enablement, centralized IaC, and deployment rollout acceleration, tied to AI and Enterprise revenue goals. - People Leadership: Grow, develop, and retain a senior-heavy team distributed across the US, Canada, and Europe, spanning FTEs and contractors, with a focus on succession planning and bench depth. - Vendor Management: Own multi-million-dollar AWS spend accountability and contractor oversight, with a savings-pipeline mindset baked into planning. Qualifications: - Deep AWS infrastructure mastery: EKS, networking (VPC/TGW/DNS), and Terraform at scale, with strong architectural judgment and a track record of setting technical direction. - Strategic roadmap ownership: Track record setting 6–12 month cloud roadmaps tied to business outcomes across enterprise, AI, and cost. - Cross-team influence: Builds genuine partnerships across Product, Security, SRE, and DB orgs, driving shared ownership across traditional infra/product boundaries. - Application-level curiosity: Genuinely understands what the product does, not just the infrastructure underneath, and extends ownership past traditional platform boundaries. - People leadership at scale: Proven experience growing and retaining senior-heavy, geographically distributed teams across FTE/contractor blends; builds bench depth and succession plans. - Operational rigor: Strong on-call instincts, incident ownership, and RCA follow-through. - Security-first instincts: This team touches blast radius (auth enforcement, network isolation, shard boundaries). A verify-first, never-assume mindset is non-negotiable. - AI & automation mindset: Demonstrated appetite for DevSecOps agents, AI-assisted IaC migrations, and skills-based automation — a core part of the near-term roadmap. - AI/ML infrastructure experience (strong plus): Scaling workloads like GPU orchestration, model-serving infrastructure, or cost-optimized compute for inference. - Education & experience: BS/MS in CS, Engineering, or equivalent. 10+ years in infrastructure/platform engineering, with significant time in a director-level role m