Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as a trusted pre-sales infrastructure advisor, designing vendor-agnostic hybrid/multi-cloud and private cloud solutions. Lead discovery, TCO/financial modeling, HLDs, SOWs, and BOMs. Guide vendor selection, present business cases to C-level stakeholders, and ensure smooth handoff to delivery teams while driving pipeline and deal growth.

Lead delivery across product, engineering, and QA for a distributed parking technology platform. Remain hands-on while improving system reliability, API architecture, integrations, CI/CD, testing, observability, and event-driven infrastructure. Partner with the AI team, sequence the roadmap, manage tradeoffs, and hire and develop engineers. Own production quality, incident response, scalability, and the evolution of partner-facing APIs serving booking channels and access-control systems.

Oversee HR operations including recruitment, onboarding/offboarding, benefits administration, HRIS/payroll support, policy drafting, employee relations, training oversight, and HR team supervision to support program departments and audits/grants.

Lead and own the agencywebsite service: design websites, set strategy, track analytics and performance, drive traffic and conversions, manage the web team and freelancers, and improve tools, processes, and growth for increased capacity and quality.

Drive new business and manage enterprise accounts through the full sales cycle: prospecting, relationship-building, solution selling, contract negotiation, and meeting revenue targets while coordinating internal teams.

Provide high-level personalized administrative support to the Chairwoman, including complex calendar and travel management, correspondence, project oversight, supervising an assistant, event logistics, preparing reports/presentations, handling confidential information, and providing concierge and family-office related services.

Lead and launch a city-based Frontier hub: raise founding capital, convene advisory and employer coalitions, hire and manage the local team, stand up programs and facilities, own full P&L, and drive measurable learner and community outcomes.

Create original city quests featuring storylines, challenges, interactive tasks, routes, descriptions, and location photos. Test quests before publication and update them as needed. The role is remote and project-based, with onboarding, creative independence, and revenue sharing. Candidates should know their local area, write and tell stories well, demonstrate creativity and attention to detail, and work reliably and independently.

Manage daily operations across departments, develop and implement procedures to increase efficiency, lead and train staff, oversee supply chain and budgets, analyze operational metrics, enforce safety, perform hands-on tasks, and maintain client/supplier relationships to ensure timely, quality service.

The Sales Executive develops new customer relationships, maintains existing accounts, meets sales metrics, and manages territory coverage while representing the company at trade shows.