Top Tech Jobs & Startup Jobs in Chicago, IL

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.

The Sales Development Representative will prospect new accounts, initiate sales cycles, qualify prospects, and build pipeline for Account Executives through cold calling, email, social selling, and AI-powered outreach. Responsibilities include using intent data and sales intelligence tools, crafting personalized messaging, collaborating with Marketing, meeting activity and opportunity targets, and developing expertise in Cleo’s AI-driven integration platform. The role offers SaaS sales training and advancement into future sales positions.

Manage a book of ~60 enterprise customers to drive adoption, retention, and expansion of Sprout's social media platform. Build executive relationships, run success cadences (MBRs, EBRs), surface risks, collaborate on renewals, and use data and generative AI tools to create ROI narratives and accelerate work. Partner with onboarding, professional services, and renewals to meet retention and growth KPIs.

Coordinate enterprise-wide learning and management development programs across PEAK6 and its subsidiaries. Manage program calendars, logistics, communications, participation tracking, reporting, and continuous improvement. Source, vet, and oversee external training vendors, facilitators, coaches, and content providers, including contracts, budgets, deliverables, and performance. Administer Workday Learning, maintain courses and learning paths, manage compliance training, and provide completion reports. Partner with HR leaders and business stakeholders on talent development initiatives.

Supports cross-channel marketing attribution and influence modeling by documenting data sources, defining business rules, mapping and normalizing interaction data, testing reporting prototypes, and recommending implementation steps. The intern also assists with AWS marketing data organization, segmentation research, data hygiene, process documentation, and stakeholder communications. The role requires analytical thinking, thorough documentation, clear communication, and collaboration across marketing and technical teams.

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.

Design and build web and mobile trading applications using React/React Native and .NET; extend WebSocket/REST APIs; process streaming market data; collaborate with product and vendors; troubleshoot urgent issues; apply AI coding assistants responsibly.

Full-cycle enterprise seller responsible for self-sourcing outbound pipeline, selling Edge to executive and IT buyers at regulated finance/operations companies, running discovery and demos, navigating security/procurement, and closing $100K+ production deals while maintaining CRM hygiene and working with Product/Implementation to ensure delivered scope matches sold scope.

Lead end-to-end migration from TSC1099 V1 to V2: build and run migration playbook, manage migrating accounts as senior escalation, supervise technical support/customer service team, guide clients through data mapping, testing, and validation, coordinate with development and account teams, track milestones, and transition into platform/product management post-migration.

Own end-to-end delivery of core product features, build AI/ML pipelines for construction document and drawing analysis, and shape scalable frontend, backend, and ML architecture. Collaborate with co-founders and construction users, translate workflow needs into product improvements, establish engineering practices, and help grow the team. The role spans computer vision, LLM systems, frontend, backend, and production infrastructure in a fast-moving startup environment.