Top Tech Jobs & Startup Jobs in Chicago, IL

Provide frontline support to travel advisors via chat, email, and 1:1s; troubleshoot technical issues; become a product and AI expert; create support documentation; collaborate with product and engineering to improve workflows and automate support processes.

Lead product for advisor experience, owning AI Chat, cost-to-value modeling, and a new advisor mobile app. Ship weekly enhancements, run customer research, write PRDs, QA, grow and lead the advisor team, and deliver selling and marketing tools that help advisors book more business.

Own and build a new advisor mobile app end-to-end (native shell, hybrid/web views, and Rails APIs). Ship weekly, implement release and monitoring pipelines, extend Rails APIs, and establish mobile patterns, on-call, and production ownership for a fast-moving startup.

Build and own infrastructure that turns manual agency migrations and syncs into bulk, repeatable, reliable pipelines. Harden partner syncs, consolidate per-integration logic, enforce data quality, and create idempotent, high-throughput tooling to scale onboarding.

Freelance CoPilot role for travel-industry bookkeepers and accountants to handle reporting, taxes, and financial workflows. Work project-by-project, choose assignments, and support advisors with closing-the-books tasks using Lucia’s platform. Flexible, remote contract work with platform support and competitive pay.

Define and run Tern's agency success function for enterprise travel agencies: segment accounts, build engagement models and playbooks, own post-sale activation and integration adoption, run business reviews tied to growth, surface product feedback to R&D, and build scalable, AI-enabled touchpoints to drive measurable agency growth.

Lead production agentic development and build R&D tooling that accelerates team workflows. Ship weekly in the main codebase, create and improve custom agents, MCP integrations, evals, and codegen pipelines, train engineers on new workflows, and raise team standards for prompts, tooling, and autonomous throughput.

Own and build Tern's AI and data systems end-to-end: data pipelines, production AI services, evaluation harnesses, monitoring and reporting. Ensure data quality across ingestion, modeling, and reporting, ship reliable production software, and collaborate with product squads to deliver trustworthy AI features and advisor-facing analytics.

Own end-to-end supplier integrations: design, implement, test, and monitor third-party APIs. Ship weekly, improve tooling and abstractions, ensure reliability, and mentor peers. Use AI-assisted workflows to speed integration development.