Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Yahoo’s global income tax accounting operations, including consolidated and segmented tax provisions, ASC 740 disclosures, audit coordination, controls, reconciliations, and technical guidance. Manages and develops the tax accounting team while modernizing workflows through Oracle Financials, automation, and generative AI. Partners with Accounting, FP&A, External Reporting, and auditors, monitors tax law and accounting policy, and ensures accurate, timely, well-governed deliverables.

Leads company strategy and operations directly with the CEO at an early-stage payments fintech. Owns planning, goals, operating cadence, executive and board materials, cross-functional execution, operational team management, service levels, staffing, escalations, and decision analysis including pricing, corridor economics, partnerships, and market entry. Partners with product on prioritization and market strategy while managing support, product operations, and compliance operations.

Leads B2B inbound marketing strategy across acquisition, MQL generation, pipeline growth, events, and marketing operations. Oversees Salesforce-based attribution and funnel reporting, marketing technology workflows, and data integrity. Partners with Sales, Product/IT, and Account Management to drive revenue outcomes. Manages, coaches, and develops marketing professionals while improving processes, presenting data-driven recommendations, and aligning inbound, events, and operations with business goals.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Lead and scale marketing across consultancy and product studio: define positioning, run digital/social/content campaigns, implement lead-gen systems, manage internal and external teams, integrate AI and martech, track KPIs and ROI, and evolve brand voice and messaging.

Identify, attract, and assess senior healthcare leaders for clients; build and manage client relationships and a book of business; advise clients on market trends; handle full-cycle executive search and interviews; drive business development and client management.

Lead product and brand design on a freelance basis: produce developer-ready UX/UI in Figma, build and maintain design systems, craft intuitive user flows, conduct design research, collaborate with PMs and developers, and ensure on-brand visual assets across product and marketing.

Provide bilingual English and Spanish customer support by phone for top-tier client brands. Assist customers, resolve concerns, guide users toward answers, and de-escalate challenging interactions. The role requires a professional demeanor, a quiet workspace, dedicated Windows computer, quality headset, and installation of company security software and a 2FA app. Commitment is 10 hours weekly for approximately 90 days, with flexible scheduling across weekday and weekend project hours.

Lead, hire, coach, and develop a team of Enterprise Account Executives. Optimize sales workflows, pipeline management, prospecting, lead generation, and performance. Partner with Marketing, Sales Enablement, Revenue Operations, and Partnerships to drive qualified opportunities. Analyze performance data, report on pipeline metrics, and help the team achieve or exceed sales targets in a fast-paced HR technology or fintech environment.

Designs, implements, supports, and optimizes high-availability telecommunications network infrastructure, including IP/MPLS, carrier Ethernet, cellular data, and video transmission systems. Responsibilities include capacity planning, bandwidth forecasting, outage troubleshooting, monitoring, documentation, project coordination, escalation management, and network security. The role also provides technical direction to junior engineers and technicians, supports small projects, and contributes to strategic infrastructure planning and continuous improvement.