Top Tech Jobs & Startup Jobs in Chicago, IL

Own enterprise sales across Texas cities, municipalities, and public infrastructure agencies. Lead complex government sales cycles from prospecting through contracting, run outcome-based pilots, convert them into multi-year agreements, navigate RFP/RFQ and cooperative purchasing processes, build ROI cases, maintain stakeholder engagement, and grow pipeline through targeted outreach, industry conferences, and an existing public-sector network.

Leads global compensation and benefits programs, including salary structures, incentive plans, equity, benefits, open enrollment, 401(k), leave administration, compliance, audits, and payroll coordination. Owns HR metrics, systems, policies, process improvements, change management, and AI-in-HR strategy. Partners with leadership, vendors, payroll, IT, and external stakeholders to improve employee experience and operational efficiency.

Own and scale Zippy’s wholesale and broker revenue channels by setting growth strategy, managing channel performance, expanding markets, developing partner acquisition and activation playbooks, and optimizing revenue. Establish metrics, reporting, operating cadence, and accountability systems; guide resource allocation; oversee partner ecosystem health; and align Growth, Product, Originations, Capital Markets, and executives around scalable execution and risk management.

Engineering interns support analysis, testing, consulting, data collection, technical calculations, field work, inspections, and engineering evaluations. They collaborate with multidisciplinary teams, prepare technical reports and presentations, apply engineering principles to client challenges, and present project results to leadership. The program provides hands-on experience, mentorship, and exposure to aerospace, energy, industrial, manufacturing, infrastructure, and emerging technology projects.

Monitor NBA and WNBA news, lineups, and storylines; create engaging social media posts for Underdog’s basketball accounts; develop evergreen content ideas; integrate products, odds, and markets into social content; and support backend administrative systems. WOOF WOOF

The Content & Prompt Operations Specialist manages AI-assisted content workflows, ensuring accuracy and engagement in content produced. Responsibilities include writing prompts, drafting content, proofreading, and improving AI outputs while following structured processes.

Independent sales contractor responsible for prospecting local businesses, booking meetings, presenting advertising opportunities on retail wellness kiosks, and closing contracts. The role offers remote flexibility, commission-based earnings, sales training, optional leads, and support from experienced representatives. Candidates should be self-motivated, proactive, results-driven, and comfortable with advertising, marketing, or media sales.

Develops and manages technology partnerships that expand Wikimedia product distribution and content reuse. Responsibilities include identifying partners, negotiating zero-dollar LOIs and MOUs, supporting attribution pilots, maintaining CRM pipelines, creating pitch materials and strategies, aligning partner needs with product roadmaps, coordinating cross-functional teams, attending industry events, and monitoring technology trends. The role requires strong technology and media connections, product fluency, negotiation skills, analytical ability, and independent program coordination.

Leads CBUSA’s strategy, P&L, revenue and margin growth, purchasing programs, vendor relationships, supply chain optimization, member services, and operational excellence. Develops budgets, KPIs, scalable processes, and reporting dashboards; negotiates strategic vendor agreements; expands membership; identifies revenue opportunities; and leads a distributed operations team. Represents CBUSA at industry events and travels approximately 50% of the time.

Conducts quality assurance evaluations and audits of customer interactions across calls, email, and chat. Analyzes CSAT, DSAT, and quality trends, performs root cause investigations, coaches frontline advisors, and supports process improvements. The role prepares reports, leads case reviews and calibration sessions, ensures compliance with client standards, and presents actionable insights to internal and external stakeholders. Requires Polish and English proficiency and is onsite in Katowice.