Top Tech Jobs & Startup Jobs in Chicago, IL

Own and grow a portfolio of $100K+ ARR strategic accounts, drive retention and multi-team expansion, run executive-level commercial conversations, influence product roadmap, win back at-risk accounts, and build the playbook for strategic account operations.

Own the full enterprise sales cycle for six-figure, multi-stakeholder deals with consumer brands exceeding $100M in annual GMV. Lead RFPs, build and defend data-driven business cases, engage executives and buying committees, manage competitive sales processes, and identify expansion opportunities. The role requires exceptional autonomy, executive presence, quota performance, and a proven record of closing enterprise accounts.

Own Siena’s end-to-end content strategy and production across founder-led LinkedIn, social media, product launches, blog posts, announcements, and video scripts. Develop the company voice, analyze content performance and trends, use AI throughout the workflow, and collaborate with the Creative Director on launch campaigns. This individual contributor role requires independently producing high-quality content for consumer brands and rapidly adjusting strategy based on evidence.

Own technical pre-sales end-to-end: run demos on real data, scope and build integrations, lead multi-week POCs, write SOWs, hand off to deployment, and drive product feedback across Sales, Product, and Engineering.