Director, Software Engineering

Responsibilities

• Lead ClickUp's Cloud Platform team to deliver reliable, cost-efficient, and scalable AWS infrastructure that stays 3–6 months ahead of product and enterprise demand.
• Bridge infrastructure and product engineering by building partnerships across product, AI, and enterprise teams to share ownership and maintain velocity.
• Set a forward-looking cloud vision, proactively align with stakeholders, and ensure the platform scales for multi-shard, multi-region growth while meeting security and compliance commitments (M365, BCDR, SOC 2).
• 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 to enable faster deployments.
• Eliminate single points of ownership across Networking, OpenSearch, and Terraform through cross-training and targeted hiring.
• Stand up recurring alignment cadence with Product, AI, Enterprise, and Security teams.
• Ship automated shard buildout via Backstage to remove manual toil.
• Cut P0/P1 incidents through hardened ingress patterns and Terraform-policy guardrails.
• Deliver 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 (FTEs and contractors) with focus on succession planning and bench depth.
• Own multi-million dollar AWS spend accountability and contractor oversight with a savings-pipeline mindset.

Requirements

• Deep AWS infrastructure mastery: EKS, networking (VPC/TGW/DNS), Terraform at scale with strong architectural opinions.
• Track record setting 6-12 month cloud roadmaps tied to business outcomes (enterprise, AI, cost).
• Cross-team influence across Product, Security, SRE, and DB orgs; ability to break "hesitant to cross the boundary" culture.
• Application-level curiosity and understanding of what the product does.
• People leadership at scale: managed and grown senior-heavy, geographically distributed teams with FTE/contractor blends; build bench depth and succession plans.
• Strong operational rigor: on-call instincts, incident ownership, RCA follow-through.
• Security-first instincts with verify-first mindset (auth enforcement, network isolation, shard boundaries).
• AI & automation mindset for DevSecOps agents, AI-assisted IaC migrations, and skills-based automation.
• BS/MS in CS, Engineering, or equivalent.
• 10+ years in infrastructure/platform engineering with significant time in a director-level role managing distributed teams.

Nice-to-Haves

• AI/ML infrastructure experience: scaling workloads like GPU orchestration, model-serving infra, or cost-optimized compute for inference.