Top Tech Jobs & Startup Jobs in Chicago, IL

Lead global engineering teams for S365 and SmartShopper, partner with Product and Architecture to deliver scalable cloud solutions, drive modernization and operational excellence, mentor managers and senior engineers, and establish engineering standards, roadmaps, and metrics to improve delivery, reliability, and performance.

Prepare and post customer invoices and payments, support collections and billing setup in NetSuite/SuiteProjects, handle customer and internal communications for billing issues, assist month-end AR close and reconciliations, support audits and external data requests, and identify process improvements to streamline accounts receivable operations.

Sell Versaterm’s SaaS public-safety solutions to assigned law-enforcement territories. Build and manage a qualified pipeline using MEDDPICC and Challenger methodologies, run demos, negotiate and close deals, collaborate with cross-functional teams, and travel to client meetings and industry events. Ensure CJIS compliance and maintain customer relationships to meet revenue targets.

Lead AI Edge content strategy and production across blog posts, newsletters, video, and creator partnerships. Produce bi-weekly newsletters, repurpose workshop recordings, coordinate creators, collaborate with SEO and paid teams, and ensure evergreen educational content that positions the brand as an authority in AI and tech.

Lead AI Edge content strategy and production across long-form articles, evergreen video, bi‑weekly newsletters, and repurposed workshop/podcast assets. Coordinate creators, partner with SEO and paid teams, and ensure all content educates, builds brand authority in tech/AI, and drives newsletter sign-ups and social engagement.

Originates and closes strategic CPG partnerships to deliver brand-funded offers, discounts, cashback, and shopper marketing programs. Builds executive relationships, negotiates seven-figure deals, drives a multi-year pipeline, represents Sezzle at industry events, and collaborates cross-functionally on product, data, marketing, legal, and finance to measure ROI and scale repeatable playbooks.

Lead developer experience strategy and build platform tooling to improve productivity, CI/CD, testing, deployment automation, and reliability. Design golden paths, reduce tooling fragmentation, collaborate across teams, and iterate on AI-assisted tooling and evaluation to enable hundreds of engineers to build, test, and ship with speed and confidence.

Lead and execute a large, cross-functional transformation (Connected Tax Platform Experience) by translating strategy into execution plans, managing dependencies, risks, governance, and release readiness. Align Product, Engineering, Architecture, UX, Data, and Operations; provide executive reporting and decision frameworks; leverage AI-assisted workflows and automation to improve delivery velocity, readiness, and customer outcomes. Coach TPM practices and drive scalable operating models for enterprise platform delivery.

Lead end-to-end proposal development for federal, state, and local government opportunities. Manage solicitation analysis, compliance matrices, schedules, writing and editing non-technical sections, coordinating reviews and production, maintaining proposal libraries, and supporting opportunity qualification and process improvements to win mission-driven work.

Identify and qualify new sales opportunities through high-volume outbound prospecting and inbound lead management. Use Salesforce, SalesLoft, and LinkedIn Sales Navigator to research, prioritize, and engage prospects, meet weekly/monthly metrics, and align with Account Executives to build pipeline.