Top Entry Level Software Jobs in Chicago, IL

Supports client pilots, onboarding, training, and adoption of an AI-powered legal platform. Designs and evaluates legal AI use cases for contract review, research, and drafting; gathers user insights, translates them into product feedback, and documents scalable deployment best practices. The role requires a completed J.D., strong communication, analytical judgment, curiosity about AI and workflow automation, and adaptability in a fast-paced, client-facing environment.

Handles high-volume payment and refund support for business travelers by contacting hotels and vendors, obtaining receipts and folios, collecting updated payment details, issuing pre-authorization forms and virtual credit cards, resolving payment issues, and coordinating credit card reversals. Maintains accurate records and timely updates while managing multiple tasks in a fast-paced, back-office environment.

Generate and qualify sales opportunities through cold outreach, inbound lead response, discovery calls, and relationship building with trucking carriers. Collaborate with Account Executives on outreach and lead handoffs, develop expertise in Toro’s transportation management software and industry, understand competitors, and consistently achieve qualified-opportunity and sourced-ARR quotas. This is an in-office Chicago role designed for upcoming graduates beginning careers in software sales.

Drive new enterprise business across assigned global accounts by generating pipeline, engaging IT, science, and data stakeholders, forecasting sales, presenting solutions, negotiating complex deals, and closing new business. Build relationships across multiple personas and executive levels, manage account data in Salesforce, collaborate with marketing, product, customer success, and partners, and apply structured sales methodologies such as MEDDICC to achieve revenue targets.

The Sales Representative will prospect new customers, manage existing client relationships, and refine sales skills while collaborating with the operations and product teams.

Owns the sales process for a cloud-based financial planning and analytics SaaS platform serving financial institutions. Responsibilities include territory planning, prospecting, pipeline development, enterprise deal management, product demonstrations, pricing and contract negotiation, forecasting in Salesforce, and cross-functional collaboration. The role requires building executive-level client relationships, achieving revenue targets, and traveling to client sites up to 50% of the time.

Support traders by troubleshooting and resolving proprietary trading system issues, documenting incidents, monitoring system components, analyzing logs, and identifying root causes. Automate manual support tasks, develop proactive monitoring tools, improve support processes, and maintain knowledge resources. The role requires collaboration with developers and peers, strong communication, critical thinking, and participation in on-call and alternate-shift coverage.

Develop and test high-performance C++ applications for trading platforms. Collaborate with traders and experienced engineers to translate requirements into efficient solutions, while monitoring, profiling, and troubleshooting systems for reliability and stability. The role provides mentorship and exposure to the complete trading-system development lifecycle, including production support, performance tuning, multithreaded programming, and real-time systems.

Leads Rundoo’s Implementation team, owning customer go-live performance, ARR attainment, resource allocation, forecasting, operating cadence, escalation processes, coaching, and cross-functional collaboration. The role builds scalable, client-centered implementation processes, improves forecast accuracy and capacity planning, and establishes accountability across Implementation Managers. Requires Chicago-based office work at least four days weekly and experience leading post-sale teams with measurable delivery or revenue targets.

Participate in a structured underwriting development program while evaluating commercial business risks, financial information, industry trends, coverage needs, and pricing strategies. Partner with brokers, customers, and internal teams to create insurance solutions, make risk-selection decisions, and support profitable growth. Build underwriting, negotiation, communication, and relationship-management skills through formal training, mentorship, and hands-on experience.