Top Tech Jobs & Startup Jobs in Chicago, IL

Whereby invites speculative applications for various roles. Applicants will be considered even if no specific openings exist, requiring a collaborative spirit and remote work adaptability.

Provide high-quality administrative, logistical, and operational support to senior executives: manage complex calendars, travel, expenses, meetings, CRM and NetSuite records, coordinate projects and events, and maintain stakeholder communications with discretion and strong prioritization.

Senior Sales Engineer responsible for technical pre-sales, solution architecture, and POCs for enterprise clients. Demonstrates platform capabilities, architects integrations with SASE, firewalls, OSes, APIs, and SIEMs, and collaborates with sales, product, and engineering to drive adoption and inform roadmap. Represents the company at industry events and stays current on cybersecurity, AI compliance, and data governance trends.

Lead partner and affiliate marketing to grow SMB deposits and support SBA digital lending. Source, onboard, and manage B2B partnerships and affiliate agencies, optimize campaigns and landing pages, track KPIs (CPA, deposit volume, LTV), analyze performance, ensure regulatory-compliant messaging, and run outbound lead generation to convert high-intent borrowers.

Own full-cycle recruiting for licensed mental health providers across multiple states. Source and engage candidates, conduct clinical screening calls, manage structured interview processes, track pipeline metrics, partner with clinical leadership to close hires, and improve ATS/workflow while ensuring licensure and compliance standards.

Analyze, design, program, test, implement and support application software and system interfaces (notably Epic and lab integrations). Lead projects, train and supervise staff, develop specifications and documentation, evaluate vendor products, coordinate installations, and maintain system improvements and quality assurance.

Plan, coordinate, and execute B2B events (conferences, tradeshows, hosted and partner events) end-to-end. Partner with marketing, sales, and customer success to define strategy, manage vendors and budgets, oversee registration and on-site logistics, track performance and ROI, and maintain event documentation and systems like Monday.com and Salesforce.

Embed with enterprise customers to design, build, and deploy production-grade integrations and data pipelines. Own technical discovery, end-to-end integration lifecycle, AI agent orchestration, customer technical relationships, and feedback to product and engineering. Produce runbooks, templates, and durable handoffs.

Design and implement large-scale product features, build and optimize backend systems and APIs, deploy via cloud and CI/CD, maintain secure reliable code, troubleshoot production issues, conduct code reviews, mentor teammates, and develop client relationships to drive digital outcomes.

Lead and maintain City Cast's visual brand across national and local channels. Create and approve sales, marketing, and campaign assets; build templates and design systems; manage design intake, contractors, and a production designer; and ensure brand consistency while enabling local flexibility and revenue storytelling.