Top Tech Jobs & Startup Jobs in Chicago, IL

Own the CEO’s strategic execution, cross-functional initiatives, priority tracking, operational monitoring, executive communications, hiring infrastructure, and administrative support. Drive projects across Operations, Sales, and Marketing, identify risks, improve processes, maintain CRM and workflows, coordinate events, and build AI-enabled automations. Translate business needs into technical specifications and BRDs while supporting organizational growth and keeping the CEO’s office effective.

Owns data-driven copy experimentation across the full growth funnel, including paid acquisition, landing pages, intake flows, checkout, lifecycle email and SMS, push notifications, and retention campaigns. Uses customer insights, analytics, and A/B testing to improve conversion, activation, adherence, and lifetime value. The role also develops compliant, empathetic messaging for sensitive healthcare topics and leverages AI tools to scale copy production.

Drive revenue by upselling and cross-selling cloud-based travel, expense, accounts payable, and payments solutions to existing SMB clients. Manage prospecting cadences, client meetings, sales opportunities, pipeline, forecasting, presentations, negotiations, and Salesforce documentation. Partner with Client Success, Solutions Consulting, sales management, and other stakeholders to exceed quarterly and annual quotas.

Supports treasury operations by analyzing payroll and transaction data, monitoring bank transactions, preparing and releasing payroll files, processing ACH requests, tracking funding limits, resolving payment issues, and generating reports on trends and anomalies. The role also assists customers and collaborates with banks and internal teams to ensure accurate, compliant, and timely financial processing.

Leads creative strategy and production for federal client campaigns while personally creating graphics, video, motion, photography, and social content. Manages a multidisciplinary creative team, oversees production partners, presents concepts, manages workflows across contracts, and ensures accessibility and brand compliance. Develops proposal materials and introduces AI and other tools to improve creative efficiency.

Lead and support oversight of fintech partner audits within the Banking-as-a-Service program. Responsibilities include developing risk assessments, planning and coordinating audits, evaluating scopes and reports, tracking remediation, analyzing risk trends, supporting regulatory compliance, and collaborating with internal subject matter experts, partners, and audit firms. The role also contributes to process improvements, staff training, and recommendations to risk management leadership.

Manage the 12-month GovRAMP compliance project by developing plans, coordinating Security, Engineering, IT, Compliance, vendors, and assessors, tracking milestones and dependencies, maintaining risks and issues, and reporting status to the CISO and stakeholders. Coordinate evidence collection, remediation, assessments, documentation, and authorization milestones while driving accountability without direct authority.

High-performing outbound SDR responsible for building and accelerating pipeline through 3-4 hours daily cold calling, AI-orchestrated high-velocity prospecting, managing AI agents, strategic outreach via phone/LinkedIn/email, and maintaining HubSpot CRM data integrity to source qualified meetings for New Business Directors.

Leads data science research from question framing through modeling, validation, and recommendations. Partners with executives, business leaders, ML engineers, and data engineers to identify opportunities in risk, fraud, retention, pricing, and compliance. Builds forecasts and production-ready models, evaluates data as a strategic asset, and translates insights into product features, offerings, and measurable business outcomes.

Performs accounts receivable accounting, federal and commercial billing, project setup, reconciliations, invoicing, month-end close, journal entries, financial analysis, and issue resolution. The role uses Oracle, IPAC, G-Invoicing, and Excel while supporting GAAP, DOE requirements, internal controls, and customer contracts. It also contributes to financial system testing, process documentation, cash management, and compliance activities.