Top Tech Jobs & Startup Jobs in Chicago, IL

Leads new business development, account growth, commercial discussions, client relationships, and sales operations for AI and GenAI data solutions. Partners with engineering, delivery, and customer success teams to understand frontier lab needs, structure projects, close opportunities, and expand client accounts. Requires quota-based technology sales experience, startup experience, STEM education, and strong AI/ML market knowledge.

Own Toloka’s global organic social media strategy across LinkedIn, X, Reddit, and YouTube. Manage executive thought leadership, write technical social copy, engage developer communities, create design briefs and multimedia assets, collaborate on content promotion, and analyze performance to optimize messaging. The role requires strong understanding of AI concepts, exceptional copywriting, executive social media experience, and hands-on skills with visual and video tools.

Owns end-to-end delivery of enterprise fine-tuning engagements, including client discovery, use-case prioritization, ROI, scope, timelines, model hosting, SLAs, security reviews, and stakeholder management. Partners with sales, product, engineering, and machine learning teams; navigates enterprise procurement and IT processes; translates between technical buyers and internal teams; and develops repeatable processes and playbooks to scale the practice.

Own product positioning, messaging, segmentation, go-to-market strategy, competitive intelligence, customer proof, sales enablement, and thought leadership for Toloka’s enterprise AI data solutions and self-service platform. Translate complex AI and machine learning capabilities into differentiated customer value while partnering with product, sales, marketing, and customers.

Lead client AI data projects from implementation through delivery, owning quality, timelines, unit economics, stakeholder transparency, and team coordination. Manage virtual cross-functional teams of engineers, supply managers, and other specialists; oversee communications, planning, status reporting, retrospectives, risk resolution, and process improvements. Projects include supervised fine-tuning data generation, LLM evaluation, and red-teaming initiatives.

Design and deliver end-to-end data labeling and ML pipelines using Toloka's platform. Act as primary technical contact for clients, lead discovery and solution design, run pilots, monitor KPIs, troubleshoot delivery, and optimize quality, cost, and scalability while coordinating internal teams and stakeholders.

Serve as the senior client-facing technical lead to design and build data-generation, labeling, and evaluation pipelines for LLMs. Partner with executive stakeholders, diagnose data needs, architect multi-stage automated solutions (RAG, agentic workflows, synthetic data), run experiments, deliver production-ready pipelines, mentor engineers, and own delivery timelines and commercial outcomes.