Director of Platform Operations – Infrastructure

Upwork; Toronto; Hybrid; CAD 120,000 - 160,000; Full time

Job summary

A leading online talent marketplace seeks a Director of Platform Operations to lead the evolution of their infrastructure in Toronto. You will oversee a globally distributed team focused on modernizing Kubernetes and platforms for AI and ML. The ideal candidate will have over 10 years of experience in software engineering, with a strong leadership background. This role offers opportunities for growth within a dynamic environment and requires onsite presence three days a week.

Qualifications

• Proven experience (10+ years) in software engineering with 3+ years leading infrastructure/platform teams.
• Deep technical expertise in cloud-native systems and Kubernetes.
• Experience designing and scaling AI/ML platforms for model training and deployment.

Responsibilities

• Lead global operations for core infrastructure platforms including Kubernetes and CI/CD systems.
• Define and execute the roadmap for secure, multi-tenant infrastructure.
• Drive automation for build and release processes and incident response.
• Oversee platform-wide observability and monitoring.
• Recruit, mentor and scale a high-performing team.

Skills

Cloud-native systems

Kubernetes

CI/CD platforms

Distributed systems operations

AI/ML platform design

Communication

Leadership

Job description

Director of Platform Operations – Infrastructure

Upwork ($UPWK) is the world’s human and AI‑powered work marketplace that connects businesses with highly skilled, AI‑enabled independent talent from across the globe. From entrepreneurs to Fortune 100 enterprises, companies rely on Upwork’s trusted platform and its mindful AI companion, Uma, to find and hire expert talent, leverage AI‑powered work solutions, and drive business transformation. With on‑demand access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, Upwork enables businesses of all sizes to scale, innovate, and build agile teams for the age of AI and beyond.

As the Director of Platform Operations, you’ll lead the evolution of Upwork’s foundational infrastructure, ensuring our platform’s resilience, scalability, and innovation‑readiness. You’ll oversee a globally distributed team driving initiatives across Kubernetes modernization, CI/CD platform services, developer tooling, and AI/ML infrastructure enablement. This high‑impact leadership role requires strategic vision, operational excellence, and deep collaboration across engineering, product, and business teams to scale Upwork’s next‑generation platform capabilities.

Responsibilities

• Lead global operations for core infrastructure platforms, including Kubernetes (EKS), developer environments, CI/CD systems, and enterprise integrations, ensuring performance, reliability, and security.
• Define and execute the roadmap for secure, multi‑tenant infrastructure that powers engineering and AI/ML workloads across the company.
• Drive automation for build and release processes, incident response, and compliance readiness while maintaining strong reliability standards.
• Oversee platform‑wide observability, including logging, monitoring, distributed tracing, and SLO instrumentation.
• Partner with AI platform teams to operationalize next‑gen infrastructure such as GPU provisioning, MCP/Agent Marketplace, and model‑serving environments.
• Recruit, mentor, and scale a high‑performing, globally distributed team that fosters innovation and technical excellence.
• Represent infrastructure operations in strategic planning and architectural reviews, influencing company‑wide platform investments and direction.

What It Takes to Catch Our Eye

• Proven experience (10+ years) in software engineering with 3+ years leading high‑performing infrastructure or platform teams.
• Deep technical expertise in cloud‑native systems, Kubernetes, CI/CD platforms, and distributed systems operations.
• Experience designing and scaling AI/ML platforms for model training, deployment, and monitoring.
• Demonstrated success in building reusable, self‑service platforms that accelerate developer productivity.
• A growth‑minded leader with exceptional communication and collaboration skills who thrives in cross‑functional environments.
• This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities.
• Interested in building your career at Upwork? Get future opportunities sent straight to your email.

Individuals in this role must be within reasonable commuting distance of Toronto, and will be required to report to an office 3 days per week.