Lead AI/ML Engineer - AI Agents

Location: Schiller Park
Posted on: June 23, 2025

Job Description:

Upwork ($UPWK) is the world’s largest work marketplace, connecting businesses with highly skilled professionals worldwide. From entrepreneurs to Fortune 100 enterprises, companies trust Upwork’s platform to access expert talent, leverage AI-powered work solutions, and drive meaningful business outcomes. Upwork’s AI-powered platform has facilitated over $20 billion in economic opportunity for professionals worldwide. With professionals spanning 10,000 skills, including AI and machine learning, software development, sales and marketing, customer support, finance and accounting, and more, Upwork empowers businesses of all sizes to scale, innovate, and build agile teams. We’re looking for a Lead AI/ML Engineer to help shape the future of intelligent systems at Upwork. In this role, you’ll design and deliver cutting-edge infrastructure and models that power agentic LLM workflows across our platform. You’ll work at the intersection of research and production, owning the delivery of advanced ML solutions and driving business outcomes through applied innovation. This role offers the chance to lead high-impact projects, support and mentor others, and help shape the future of autonomous AI agents globally. Youll work on cutting-edge machine learning initiatives that drive real business results while contributing to the broader AI research community through publications at leading conferences. Responsibilities • Architect and implement core infrastructure to support agent-based LLM systems, including multi-agent pipelines, RAG, and real-time orchestration. • Train and fine-tune custom models, including LLMs and foundation models, to solve unique Upwork-specific challenges. • Lead cross-functional collaboration across engineering, product, and research teams to align technical solutions with business impact. • Mentor and guide engineers and researchers, helping foster a high-performing, inclusive team culture grounded in AI excellence. • Translate experimental ideas into reliable, scalable production systems by applying best practices in AI engineering and deployment. • Publish and share innovations where appropriate, contributing to Upwork’s visibility in the broader AI/ML research community. What it takes to catch our eye • Strong proficiency in Python and modern ML frameworks such as PyTorch or TensorFlow, with experience developing and deploying AI systems. • Deep understanding of core ML concepts, including transformers, generative models, and agent architectures such as MCP or A2A. • Experience training large models on GPU clusters and integrating LLMs with external tools via APIs or orchestration frameworks. • Comprehensive understanding of foundational deep learning, machine learning concepts, and state-of-the-art GenAI models. • Hands-on experience training custom LLMs on GPUs and working with Retrieval-Augmented Generation (RAG) systems. • Proven ability to build end-to-end ML pipelines—from data prep and experimentation to production deployment—in a cloud-native environment. • A growth mindset, strong communication skills, and the ability to translate complex technical work to stakeholders across functions. • Demonstrated experience working in R&D environments; publications in major AI/ML conferences are a plus, but not required.

Keywords: , Rockford , Lead AI/ML Engineer - AI Agents, IT / Software / Systems , Schiller Park, Illinois