Top Tech Jobs & Startup Jobs in Chicago, IL

Lead company-wide strategy and operating cadence directly with the CEO. Manage customer support, product operations, and compliance operations; own planning, goals, service levels, executive workstreams, board materials, and cross-functional execution. Analyze corridor economics, pricing, partner performance, market entry, and build-versus-buy decisions. Support product prioritization and competitive positioning while ensuring operations scale within regulated payments and fintech environments.

Own the full enterprise sales cycle as Voidhawk’s first sales hire, from prospecting and discovery through technical evaluation, negotiation, procurement, and close. Build pipeline independently, establish repeatable sales processes, refine ICP and messaging, maintain CRM discipline, forecast accurately, and provide market feedback to product teams. The role requires selling complex security or technical infrastructure solutions to security, engineering, executive, finance, legal, and procurement stakeholders, while using AI to improve research, outreach, preparation, follow-up, proposals, and CRM workflows.

Manages and expands strategic B2B accounts by increasing revenue, developing account plans, building customer relationships, coordinating internal resources, leading solution development, and achieving sales, profitability, and customer satisfaction objectives. The role requires complex multi-location account experience, strategic planning, negotiation, CRM proficiency, and frequent overnight travel.

Leads GiveWell’s media and public affairs function, setting communications strategy, building journalist and stakeholder relationships, developing thought-leadership opportunities, managing rapid-response communications, advising executives, serving as a spokesperson, and preparing leaders for public appearances. The role also builds systems, hires and develops a growing team, oversees sensitive external communications, and ensures GiveWell’s research and mission are represented accurately and effectively.

Leads and grows a frontend-focused development team, establishes architecture and engineering practices, drives frontend roadmap execution, reduces technical debt, improves reliability and security, partners with Product and the CTO, and mentors developers. The role oversees SaaS production systems, cloud platforms, APIs, microservices, customer-focused solutions, incident response, and engineering priorities.

Own corporate FP&A forecasting, consolidations, cash flow planning, reporting, and financial modeling. Partner with Accounting and cross-functional leaders to analyze variances, improve forecast accuracy, support executive and Board reporting, and guide resource allocation. The role also enhances planning processes, automation, and models covering stock-based compensation, capital expenditures, collections, share count, and long-range planning.

Leads the North Central regional sales team, key account and builder strategies, financial planning, forecasting, P&L management, and profitable growth. Develops sales talent, manages retail and dealer relationships, monitors competitors, strengthens brand positioning, and executes regional plans across premium luxury appliance channels. The role requires travel throughout the region and occasional travel to headquarters.

Coordinates the AI Accountability Network’s newsletters, training programs, grants, fellowships, payments, events, communications, and community initiatives. Manages editorial workflows, contractors, applications, logistics, websites, listservs, dashboards, metrics, and stakeholder communications. Supports grant administration, funder reporting, travel, curriculum development, and website publishing while improving processes and tracking program impact.

Supports and enhances a pension administration system by gathering requirements, documenting processes, analyzing issues, coordinating with stakeholders and vendors, and conducting functional, integration, regression, and user acceptance testing. Performs data validation, reconciliation, reporting, process improvement, change management, and implementation support. The role also tracks defects, risks, decisions, dependencies, and project activities while ensuring system changes meet business and operational needs.

The Managing Consultant leads cybersecurity engagement scoping, proposal development, technical project coordination, client communication, report review, and delivery oversight. The role supports Directors and business development teams, troubleshoots technical execution issues, manages client relationships, mentors Security Consultants, and may perform limited hands-on consulting. Candidates need offensive security experience, strong client-facing communication, technical scoping and estimation skills, and the ability to translate complex findings into actionable recommendations.