Top Tech Jobs & Startup Jobs in Chicago, IL

Own the technical side of standard B2B SaaS sales cycles, including discovery, solution scoping, demonstrations, POCs, RFP responses, and technical handoffs. Advise customers on EDI, supply chain connectivity, ERP integrations, APIs, and AI capabilities. Collaborate with Sales, Product Management, Customer Success, and Professional Services while managing multiple opportunities and creating reusable presales assets.

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.

Implements B2B EDI and integration solutions for enterprise clients. Responsibilities include analyzing data and business processes, designing mappings, configuring and deploying customer solutions, explaining architecture, supporting project delivery, and collaborating across teams. The role develops expertise in Cleo Integration Suite, APIs, communication protocols, ERP integrations, automation, and AI-assisted implementation documentation and coding.

Owns end-to-end EDI and integration implementations for enterprise customers. Configures EDI, APIs, communication protocols, ERP integrations, business processes, and data mappings; implements REST and SOAP APIs with OAuth; performs testing and troubleshooting; and supports customer workshops, UAT, and issue resolution. The role requires customer-facing implementation skills, supply chain integration knowledge, and the ability to use AI tools to accelerate project delivery.

Identify and prospect new accounts across target European countries, generate qualified opportunities through outbound calling, email, and social selling, and build pipeline for the EMEA sales team. The role involves qualifying prospects, tailoring account messaging, collaborating with Marketing, explaining Cleo’s value proposition, meeting monthly activity and opportunity targets, and developing expertise in Cleo’s products, supply chain technology, and sales tools.

Lead technical delivery of complex EDI, API, ERP, and B2B integrations from implementation through hypercare. Configure workflows, data mappings, APIs, security, and communication protocols; troubleshoot production issues and optimize performance. Serve as the primary technical contact for customers, lead workshops and UAT, manage escalations, and collaborate with project managers and architects. Mentor junior engineers, conduct code reviews, and promote reusable engineering practices and documentation.

Leads technical support operations for complex EDI, API, and file-transfer incidents. Acts as incident commander for P1/P2 issues, performs root-cause analysis, oversees queue health and SLA adherence, governs backlog reduction, mentors engineers, and drives alert tuning, process improvements, automation, and AI-enabled operational enhancements.

Own Cleo’s application and product security program across SaaS and customer-hosted products. Lead SSDLC practices, threat modeling, security tooling, vulnerability management, penetration testing, coordinated disclosure, CVE publication, and NIST CSF controls. Define product security standards, roadmap, secure defaults, access controls, and customer-facing advisories. Partner with engineering, product, architecture, and customers while guiding security engineers and consultants. Also establish protections for LLM applications, AI agents, and AI-assisted development workflows.

Manage customer-facing technology implementation projects from kickoff through closure, owning scope, schedule, budget, quality, risks, and delivery outcomes. Coordinate customers, executives, implementation engineers, and cross-functional teams across multiple concurrent projects. Lead planning, status communication, forecasting, resource management, and budget tracking. Apply and help develop AI-enabled PMO workflows, while communicating the value of cloud-based B2B integration solutions. Travel approximately 15% for customer visits, partner meetings, events, and team planning.

Leads technical pre-sales for supply chain integration solutions, partnering with Sales to conduct discovery, design ERP/WMS/TMS and trading-partner architectures, run POCs, deliver demonstrations, and respond to RFPs. Advises technical and executive stakeholders on business outcomes and AI opportunities, translates capabilities into measurable ROI, and collaborates with Product, Customer Success, and Professional Services on roadmap feedback and post-sale handoffs.