Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale Tern's enterprise sales motion as a player/coach: carry personal enterprise quota, co-sell, run weekly HubSpot pipeline reviews, define ICP with marketing, codify playbooks, recruit and ramp AEs, and improve forecasting and pipeline hygiene to accelerate larger, faster deals.

Lead and own supplier integration architecture and implementation end-to-end. Ship first cruise and lodging integrations, write production-ready code, establish integration patterns, build tooling and AI-assisted workflows to accelerate future integrations, monitor production reliability, and coach another engineer while remaining hands-on.

Own and build Tern’s financial infrastructure: service fee collection, billing, invoicing, GL flows, month-end close, exports, and enterprise reconciliation. Partner with engineering and the Head of Product, ship compliance and risk foundations, and scale payments, virtual cards, payroll, multi-currency, and accounting integrations.

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.

Build and run Tern's top-of-funnel demand generation for agency customers: define qualified lead targets, instrument tracking and attribution, run rapid experiments, launch repeatable campaigns, manage paid/content/tooling budgets, refine ICP with sales, and continuously optimize channels to hand qualified leads to sales.

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.

Lead and scale Tern’s support and education function for 20,000+ travel advisors. Build AI-driven support workflows, content production, and curriculum; manage a distributed team (~8), partner with R&D and implementation, and own activation, FRT, CSAT, AI resolution, and adoption metrics.

Own the Heroku-to-GCP migration, maintain Postgres and data pipelines, optimize high‑traffic code paths, build monitoring/alerting, lead incident response and post‑mortems, reduce costs and scale proactively, and coach other infrastructure engineers.