Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the full enterprise sales cycle for Tier 1 accounts: prospect and close deals with C-level executives, develop sales frameworks, pursue greenfield verticals, manage pipeline and forecasting in Salesforce, exceed quarterly targets, and coordinate handoffs with implementation and cross-functional teams.

Lead end-to-end migration from TSC1099 V1 to V2: build and run migration playbook, manage migrating accounts as senior escalation, supervise technical support/customer service team, guide clients through data mapping, testing, and validation, coordinate with development and account teams, track milestones, and transition into platform/product management post-migration.

The Customer Solutions Engineer manages system integrations, provides technical support, troubleshoots complex issues, and optimizes operational systems while collaborating with clients.

As an Account Executive, you'll manage the entire sales process, focusing on outbound sales, lead generation, and building relationships with customers in the Chicago area, with frequent travel to meet clients.

The AI Engagement Manager will lead strategic relationships with clients to implement AI solutions, driving business transformation and optimizing operations in the housing sector.

Lead and scale a multi-product engineering organization, define technical and AI-first strategy with Product/GTM, drive engineering excellence and scalable architecture across frontend/backend/infrastructure, accelerate AI-assisted workflows, remove execution blockers, and foster a strong ownership-focused engineering culture.

Own end-to-end enterprise sales into large multifamily owners: prospect, demo, negotiate, close, launch and expand accounts. Spend significant face-to-face time in market, sell to C-suite, manage complex multi-threaded deals, partner with Customer Success and Product, and help build sales playbooks and processes.

As an Infrastructure Engineer, you will develop and maintain systems, triage issues, and manage Linux environments, working both independently and as part of a team.

Supports a portfolio of clients through proactive communication, issue resolution, onboarding, adoption campaigns, renewals, training coordination, and self-service enablement. Maintains CRM records, monitors client engagement and utilization, identifies retention or growth risks, and collaborates with internal teams to deliver consistent service. The role follows established playbooks while supporting high-volume client portfolios and peak-season financial reporting and proxy services.

The Senior Software Engineer will design and build cloud-native applications, lead technical initiatives, and mentor junior developers while collaborating with the product team.