Top Tech Jobs & Startup Jobs in Chicago, IL

The Regional Sales Manager is responsible for driving new business and managing customer relationships in the transit tech sector, focusing on consultative selling and sales execution.

Own full-cycle, multi-state payroll for more than 1,000 employees using Rippling. Manage payroll tax accounts, filings, notices, reconciliations, audits, benefits, 401(k), workers’ compensation, year-end reporting, and payroll accounting. Serve as Rippling system owner, maintain payroll documentation, and build AI-enabled automation for payroll support, reporting, agency notices, and audit preparation.

Own Dispatch’s day-to-day legal function as a hands-on commercial attorney. Responsibilities include negotiating enterprise SaaS agreements, MSAs, order forms, DPAs, security addenda, privacy and data-sharing arrangements, employment agreements, vendor contracts, and other operational matters. The role partners with Sales, Product, Engineering, Security, Finance, People, and executives; builds scalable legal templates and playbooks; supports compliance processes; manages outside counsel; and establishes the legal infrastructure for company growth.

Partner with Sales, Credit Risk, Legal, Product, and Capital Markets to model and price credit deals, build life-of-loan portfolio and vintage models, stress-test revenue-share and capital scenarios, support sponsor bank and capital provider pitches, lead deal reviews, and develop AI-enabled tools and dashboards to scale credit deal modeling and decisioning.

Drives communications, marketing, events, and project execution across multiple workstreams. Coordinates event strategy, logistics, vendors, venues, technology, budgets, and attendee experiences. Creates and publishes social media, website, newsletter, presentation, and thought leadership content. Tracks digital performance metrics, manages publishing operations, develops work plans, coordinates stakeholders, resolves issues, and creates contingency plans. The role is remote or hybrid and requires travel of up to 25%.

Leads technical business development and capture activities, identifying market opportunities, developing tailored technology solutions, and cultivating client and partner relationships. Collaborates with engineering, product management, and marketing teams; leads proposals, presentations, negotiations, and contract pursuits; and tracks business development KPIs. Requires extensive technology-sector sales experience, technical communication skills, and Secret clearance with eligibility for Top Secret clearance.

Lead the engineering organization and technical strategy while remaining hands-on across web, mobile, backend, infrastructure, architecture, and AI. Own the technical roadmap, design scalable production systems, establish engineering standards, mentor and grow engineers, and drive AI-assisted development. Partner with Product and executive leadership to balance speed, reliability, security, scalability, and quality while building systems with Golang, TypeScript, and GCP.

Localize Speak’s in-app learning and marketing content into Traditional Chinese, translate from Japanese, and create Japanese learning materials for Traditional Chinese learners. Responsibilities include translation, pedagogical editing, QA, lesson and vocabulary development, content project support, script uploads, and collaboration with international teams. The role requires native Traditional Chinese, near-native Japanese, translation expertise, Japanese teaching or curriculum experience, strong English proficiency, and interest in AI-assisted language learning.

Own full-cycle new customer acquisition for SMB and mid-market accounts, from outbound prospecting and qualification through demonstrations, trials, negotiation, and close. Generate most pipeline independently, manage high-volume opportunities, sell through channel partners, maintain accurate CRM and forecasts, and communicate mobile security value to lean IT and security teams. The role also contributes to sales playbooks, collaborates cross-functionally, and requires occasional territory travel.

Lead end-to-end creative production for digital, branding, design, and spatial projects. Manage client relationships, cross-functional teams, timelines, budgets, scope, quality assurance, reporting, and issue resolution. Mentor junior producers and collaborate with designers, developers, strategists, technical teams, and external partners. The role requires strong creative project management experience, familiarity with Agile practices, and travel for client interactions, shoots, site visits, activations, and workshops.