Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full sales cycle for mid-market real estate brokerages, from outbound prospecting and discovery through product demonstrations, multi-stakeholder negotiations, and closing. Build and manage a healthy pipeline, achieve quarterly quota, maintain accurate CRM forecasts, attend industry events, and collaborate with business development, product, onboarding, and customer success teams. The role requires PropTech and mid-market B2B SaaS sales experience, consultative selling skills, and quarterly travel.

Own the strategy, roadmap, and results for AI-powered marketing products spanning discovery, content, websites, email, social, and paid channels. Drive product quality, cross-channel integration, measurement, attribution, client adoption, retention, and revenue. Lead customer betas, develop business cases, and collaborate with engineering, design, AI/ML, client success, and sales to deliver high-impact marketing automation capabilities.

Own go-to-market financial planning, forecasting, reporting, and efficiency analysis across Sales, Marketing, and Customer Success. Build models for CAC, LTV, payback, capacity, and productivity; analyze financial and operational data using SQL; automate recurring reporting; and advise senior leaders on GTM investment decisions and resource allocation.

Lead and grow a hands-on Maps & Search engineering team owning home search across web and mobile. Set technical direction, contribute to code, and scale a high-throughput search platform (~1B monthly requests). Improve relevance, latency, and reliability, integrate AI/LLMs into discovery and ranking, and drive delivery from roadmap through incidents and production operations.