Director, Software Engineering - Infrastructure at ClickUp – United States | Jobyssey

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: BS/MS in CS, Engineering, or equivalent.
Experience: 10+ years in infrastructure/platform engineering, with significant time in a director-level role managing distributed teams.

Equal Opportunity Employer

ClickUp is an Equal Opportunity Employer, and qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin.

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Visa Sponsorship

Please note we are unable to sponsor or take over sponsorship of an employment visa for roles outside of engineering and product at this time. Sponsorship for engineering and product roles is not guaranteed, but is instead based on the business needs for that specific role at that time. Please reach out to the recruiter with any questions.

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