Top Tech Jobs & Startup Jobs in Chicago, IL

Build and productionize applied AI/ML systems (predictive ordering and agentic copilots) end-to-end, drive measurable business KPI impact, collaborate with product/engineering, implement model-ops, observability, HITL workflows, and mentor peers.

The Account Executive is responsible for sourcing, qualifying, and closing new restaurant partners, maintaining sales pipelines, and ensuring successful partnerships.

Lead commercial growth for 3-5 Tier 1 retail accounts post-sale: own expansion, renewals, and ARR through account planning, upsell, negotiation, executive engagement, and cross-functional collaboration. Use data-driven strategies, Salesforce and Trumpet for pipeline and forecasting, and partner with Customer Success, Product, and Marketing to realize customer value and scale long-term enterprise relationships.

Lead the development of procurement strategies, drive vendor management, ensure cost savings, and establish procurement processes in a remote-first environment.

Build and lead Headway's procurement function: define procurement strategy and policy, manage vendor lifecycle, drive cost optimization and strategic sourcing, implement procurement tooling and reporting, advise leadership on governance and risk, and hire and develop a high-impact procurement team.

Own end-to-end lending products (origination, underwriting, servicing) and roadmap. Lead integrations with sponsor banks, credit bureaus, and loan management software. Collaborate with engineering, design, risk, data science, compliance to build underwriting, decisioning, and servicing experiences; run A/B tests and document underwriting logic to meet regulatory requirements.

Lead design and implementation of secure global network infrastructure. Architect security standards, conduct threat modeling and network assessments, build security automation and tooling, integrate controls with SDN/BGP/MPLS platforms, support incident response, and mentor engineering teams to maintain resilient, observable network security posture.

Lead planning and execution of regional brand activations across the Western U.S., including venue sourcing, vendor coordination, on-site logistics, budget management, localizing national campaigns, building partner relationships, and serving as primary regional stakeholder contact. Significant in-market travel required to support activations and ensure ROI and consistent execution.

Prepare and file individual and business tax returns involving bitcoin and digital assets. Provide cryptocurrency tax planning, calculate cost basis and gains or losses, maintain compliance records, collaborate with financial and estate planning teams, monitor regulatory changes, and contribute to thought leadership through articles, webinars, and industry events.

Hunt and close net-new revenue by selling programmatic and omnichannel media solutions. Prospect and engage senior marketing decision-makers, conduct discovery and data-driven presentations, develop customized campaign recommendations with internal teams, maintain a qualified CRM pipeline, and meet revenue and performance targets.