Top Tech Jobs & Startup Jobs in Chicago, IL

Own the complete B2B sales cycle, from outbound prospecting and pipeline generation through presentations, negotiation, and closing. Build relationships with decision-makers, manage opportunities in CRM systems, meet revenue and activity targets, and collaborate on client onboarding and success. The role requires a highly motivated sales hunter capable of selling complex technology solutions and consistently generating new business.

Advise prospects on Billtrust’s invoice-to-cash SaaS solutions through configured demonstrations, requirements gathering, presentations, proposals, and Statements of Work. Collaborate with sales, partners, marketing, and development teams to align solutions with customer needs, resolve complex issues, manage scope, and support new-business opportunities. Use AI tools to accelerate demo configuration and proposal drafting while applying deep credit, collections, accounts receivable, and invoice-to-cash expertise.

Designs and iterates enterprise go-to-market playbooks, AI-powered outbound strategies, targeting and segmentation frameworks, and strategic campaigns. Analyzes prospect and market feedback, builds consultant and broker partnerships, tests growth automation, and presents data-driven recommendations to leadership. The role requires cross-functional collaboration with sales and marketing teams, prospect engagement, and travel to events and strategy sessions.

Own Anza Exchange end to end, including strategy, growth, product roadmap, transactions, and P&L. Scale a pilot marketplace into a two-sided B2B platform by building supply and demand, refining deal workflows, partnering with engineering, growing commercial adoption, hiring the team, and reporting performance and investment needs to executive leadership.

Executive Assistant supporting company founders with business, personal, and operational tasks. Responsibilities include project coordination, expense reporting, travel planning, scheduling, event management, communications, confidential information handling, and follow-up tracking. The role requires strong organization, accuracy, discretion, communication, spreadsheet skills, flexibility, and the ability to work independently in a fast-paced remote environment.

Own enterprise demand generation programs for a defined ABM target list. Responsibilities include account prioritization, outbound campaigns, executive dinners, conferences, field marketing, customer proof, case studies, and sales follow-up. The role is a senior hands-on individual contributor responsible for generating qualified pipeline and revenue, partnering with Sales, delivery, agencies, leadership, and technical experts. Regular travel is required for events.

Leads Propel America's product and technology strategy, including the Fellow Portal, AI integrations, technology roadmap, software development, Salesforce, infrastructure, data systems, cybersecurity, and vendor relationships. Manages technical staff and outsourced IT providers, oversees architecture, QA, releases, compliance, data privacy, and disaster recovery, and partners cross-functionally to translate organizational needs into scalable products and technology solutions.

Executes full-cycle recruiting by sourcing candidates, coordinating interviews, maintaining ATS data, tracking recruiting metrics, managing stakeholder communications, and driving hiring processes from outreach through offer acceptance. Partners with hiring managers and leadership to refine sourcing strategies, remove bottlenecks, improve workflows, and deliver a strong candidate experience in a fast-paced startup environment.

Owns production infrastructure across Kubernetes, CI/CD, Linux systems, virtual machines, and AI accelerator environments. Responsibilities include incident response, troubleshooting, automation, monitoring, alerting, patching, upgrades, certificate renewals, capacity checks, runbook development, and on-call support. The engineer collaborates across IT and product software teams and contributes to infrastructure design and build work.

Leads BlueCat’s global Mid-Market sales organization across North America, EMEA, and APAC. Owns go-to-market strategy, bookings and ACV targets, pipeline generation, forecasting, partner-led sales, coverage models, quota capacity, and regional execution. Develops sales leaders and teams, establishes activity-based operating rhythms, drives new-logo acquisition and account expansion, and collaborates cross-functionally to support scalable growth. Reports to the Chief Revenue Officer and travels frequently worldwide.