Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Brigit's product organization across product management, design, and research. Own product vision, roadmaps, and outcomes (acquisition, conversion, engagement, monetization). Build and scale cross-functional teams, drive data-informed experimentation, and partner with engineering, data, and marketing to optimize product velocity and business metrics in a regulated consumer fintech environment.

Design, build, and own scalable data pipelines and evaluation systems that power production AI features and internal analytics. Ensure data quality across ingestion, modeling, and reporting, collaborate with ML and analytics teams, deploy and monitor ML systems, and establish standards for data work and evaluation.

Serve as the technical lead for partner integrations of DNSid: design and build production-grade integrations, run POCs and workshops, produce enablement materials, translate partner requirements into product feedback, and own the path from demo to deployment while collaborating with product, standards, and engineering teams.

Lead and manage the Dispute Defense team to minimize chargeback risk and fraud, oversee dispute responses and collections, ensure timely submissions, monitor chargeback ratios, report win rates, collaborate with processing partners, and drive process improvements and AI-driven automation to reduce manual workflows.

Manage delivery of a portfolio of AI and data science projects from planning through implementation. Coordinate technical and non-technical teams, dependencies, requirements, budgets, timelines, and stakeholder expectations. Lead Agile ceremonies, drive accountability, translate AI capabilities into actionable requirements, and proactively identify and mitigate risks across complex, concurrent initiatives.

Supports the CEO and President by managing calendars, travel, meetings, communications, briefing materials, events, information flows, and confidential matters. The role coordinates high-volume domestic and international travel, prepares written materials, tracks workstreams, liaises with internal and external stakeholders, and ensures principals are prepared for engagements. Success requires exceptional organization, discretion, judgment, adaptability, communication, and comfort working remotely in a fast-paced environment.

Support trading regulatory compliance for sports wagering across jurisdictions by partnering with Trading, Legal, and Regulatory Operations; track and update regulatory requirements; design controls and processes; obtain regulator approvals for new offerings; support launches and submissions; identify compliance risks and recommend solutions to ensure operational efficiency and regulatory adherence.

Lead analytics engineering for Revenue, Marketing, and Finance by building scalable data solutions, data models, and dashboards; provide training and consultation, support ad hoc data needs, and translate technical findings into executive-level insights to improve operational performance.

Provides remote administrative support by managing emails, calls, calendars, meetings, travel arrangements, contact lists, spreadsheets, online records, market research, presentations, employee inquiries, and customer service. Requires strong communication, organization, time management, familiarity with cloud, VoIP, desktop-sharing, word-processing, spreadsheet, and online-calendar tools, plus a high school diploma.

Monitor real-time contact center volumes, agent adherence, and staffing; manage time-off and schedule adjustments; analyze trends in attendance and service metrics; recommend staffing optimizations; maintain confidential employee records and generate reports using workforce management tools and spreadsheets.