Director, Machine Learning

About the role

Lead the engineering organization responsible for connecting millions of clients and freelancers on Upwork's platform. This role involves shaping the future of Upwork's matching capabilities, from search to conversational AI, by setting technical direction and scaling core systems. It's a high-impact leadership position guiding a strong engineering team in partnership with product and executive leadership.

Key facts

What you'll do

• Define and implement the technical strategy for Upwork's Search & Recommendations platform, ensuring alignment with business goals and platform scalability.
• Lead and develop a high-performing team of software and machine learning engineers, fostering a culture of ownership and continuous learning.
• Deliver a unified Search & Recommendations platform that powers matching experiences across client and talent journeys.
• Modernize search infrastructure by migrating from older systems to scalable, high-performance architectures with clear APIs and strong experimentation support.
• Collaborate with product, ML, data science, design, and senior leadership to prioritize roadmaps and translate platform decisions into measurable business outcomes.
• Promote engineering excellence through strong practices in system reliability, data integrity, and responsible AI development.
• Establish clear operating mechanisms, metrics, and team rhythms to improve execution and track platform health and business impact.

Requirements

• Significant experience leading engineering teams in high-scale environments.
• Proven track record of delivering search, recommendations, ranking, or retrieval systems that achieve business results.
• Deep technical understanding of distributed systems, data pipelines, search architecture, and modern machine learning infrastructure.
• Ability to guide architecture decisions and mentor senior engineers and managers.
• Demonstrated success leading integrated teams of software and machine learning engineers.
• Strong ability to build partnerships across product, data science, and executive stakeholders.
• Capacity to operate effectively at multiple levels, translating technical depth into strategic clarity.
• Skill in making sound decisions in ambiguous, fast-moving environments.
• Strong applied understanding of AI-native engineering workflows, including using AI to accelerate design, experimentation, and delivery.

Practical notes

This position is eligible for an annual bonus plan or sales incentive plan and participation in the long-term equity incentive program. Upwork offers comprehensive medical coverage, unlimited PTO, a 401(k) plan with matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan. Upwork hires full-time employees in 34 U.S. states. A criminal background check may be required after a conditional job offer. Upwork uses BrightHire, an AI-enabled tool, to record interviews and summarize transcripts; candidates can opt out of recording.