Director, Software Engineering

ClickUp is an AI-native company focused on building the future of work with a converged AI workspace. They are seeking a Director of Software Engineering to lead the Cloud Platform team in delivering scalable AWS infrastructure while ensuring alignment with product and enterprise demands.

Responsibilities:

• Drive millions in annual savings by migrating data workloads to EKS and self-hosting OpenSearch on EKS
• Deprecate legacy frontend ALBs and consolidate to a single EKS-managed ALB per shard, unblocking faster deployments across the org
• Eliminate single points of ownership across Networking, OpenSearch, and Terraform through cross-training and targeted hiring into coverage gaps
• Stand up a recurring alignment cadence with Product, AI, Enterprise, and Security so infra planning is driven by demand, not ad-hoc interrupts
• Ship automated shard buildout via Backstage to remove manual toil from enterprise scaling
• Cut P0/P1 incidents attributed to Cloud Platform (DNS, ALB misconfiguration) through hardened ingress patterns and Terraform-policy guardrails, including blocking unauthenticated public endpoints
• Deliver a Q3/Q4 roadmap covering Agent enablement, centralized IaC, and deployment rollout acceleration, tied to AI and Enterprise revenue goals
• Manage a senior-heavy team distributed across the US, Canada, and Europe, spanning FTEs and contractors, with a focus on succession planning and bench depth
• Own multi-million dollar AWS spend accountability and contractor oversight, with a savings-pipeline mindset baked into planning

Requirements:

• Deep AWS infrastructure mastery: EKS, networking (VPC/TGW/DNS), Terraform at scale. Strong architectural opinions, not just operational chops
• Strategic roadmap ownership: Track record setting 6-12 month cloud roadmaps tied to business outcomes (enterprise, AI, cost), not only tech debt cleanup
• Cross-team influence: Navigates Product, Security, SRE, and DB orgs fluidly. Must break the 'hesitant to cross the boundary' culture
• Application-level curiosity: Genuinely understands what the product does, not just the infra underneath. Ownership extends past traditional platform boundaries
• People leadership at scale: Managed and grown senior-heavy, geographically distributed teams across FTE/contractor blends. Must build bench depth and succession plans
• Operational rigor: Strong on-call instincts, incident ownership, 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: Real appetite for DevSecOps agents, AI-assisted IaC migrations, and skills-based automation. This is on the Q3 roadmap, not a nice-to-have
• AI/ML infrastructure experience: Scaling workloads like GPU orchestration, model-serving infra, or cost-optimized compute for inference is a strong differentiator
• Education & experience: BS/MS in CS, Engineering, or equivalent. 10+ years in infrastructure/platform engineering with significant time in a director-level role managing distributed teams