Top Tech Jobs & Startup Jobs in Chicago, IL

Full-cycle Account Executive selling Hospitable's short-term rental platform and Align insurance to inbound real estate investor leads. Diagnose client operations, configure software live, obtain P&C license within 30 days, quote insurance, close deals, manage renewals, and keep accurate CRM and agency records.

Lead enterprise software sales and customer success for iBusiness.ai. Drive revenue, adoption, renewals, expansions, and commercialization of AI and automation products. Build commercial discipline, coach teams, improve forecasting and pipeline quality, represent the company externally, and align cross-functional teams to scale software business growth.

Own the full sales cycle for MSSP accounts across the U.S., build territory and outbound pipeline, shape the MSSP go-to-market playbook, collaborate with cross-functional teams, and close complex consultative B2B cybersecurity deals focused on faster investigations and recurring revenue.

Hunt and close new higher-education and business SaaS accounts, expand existing accounts, manage long sales cycles, present demos, negotiate contracts, shape GTM strategy, and maintain pipeline and forecasts.

Design, implement, and own production platform subsystems for an enterprise AI control plane. Deliver production-ready Go services on Kubernetes, ensure reliability, observability, and scalability, mentor engineers, drive design docs and code quality, and contribute to the open-source ToolHive/MCP ecosystem.

Lead and scale paid mobile acquisition across ASA, Google, Meta, DSPs and other channels. Build measurement systems connecting spend to subscription revenue and LTV, run repeatable testing frameworks, drive creative strategy, use AI to speed reporting and optimization, and establish operating rhythms for budgeting, experiments, and performance forecasting.

Own and build the US sales pipeline for Terrific: identify and prospect brands, retailers, agencies and partners; run discovery; develop proposals, pilots, and negotiations; close new recurring revenue; collaborate with Customer Success, Product, and Marketing to scale opportunities and improve GTM strategy.

Lead global sales and RevOps to drive sustainable revenue growth for a music-focused B2B SaaS. Set GTM strategy, own revenue targets, coach and scale the sales organization, improve forecasting and CRM hygiene, close strategic enterprise deals, and align Sales, Marketing, Customer Success and Product to increase conversion, expansion, and retention.

Build and scale an agentic AI stack for healthcare revenue cycle: implement voice AI pipelines, LLM orchestration, integrations with EHRs/RCM systems, real-time analytics, dashboards, and production-grade full stack features working closely with founders and customers.

Drive upstream sales strategy and specification penetration for insulation products across assigned western territories. Provide technical expertise, educate customers, attend site visits, translate market needs to marketing, and capture commercial market share in sectors like education and healthcare.