Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a globally distributed Java engineering organization responsible for enterprise software design, development, modernization, quality, and delivery. Manages engineering leaders and teams, drives technical strategy, process improvement, Agile and CMMI-aligned execution, and coordinates customer commitments with long-term platform modernization. The role requires strong enterprise Java architecture expertise, executive communication, organizational leadership, and experience managing complex delivery priorities, technical debt, quality standards, and engineering performance.

Leads and develops a data engineering team implementing Navigate360 integrations for partner campuses. Oversees integration design, data mapping, validation, reconciliation, quality controls, delivery planning, and scalable implementation processes. Partners with Product, Launch, and Partner Success teams to resolve technical and partner challenges, improve adoption, manage project health, and ensure reliable outcomes. Provides technical mentorship, code and design review, stakeholder communication, and continuous process improvement.

Manage employer stop-loss insurance renewals and new account implementations. Review submissions, RFPs, underwriting files, and proposal data for accuracy and completeness; resolve broker discrepancies; negotiate with stop-loss markets; prepare applications and renewal notices; maintain quote qualifications; and coordinate account issuance. The role also involves managing a profitable book of business, collaborating with brokers, clients, third-party administrators, and internal teams, and delivering accurate, timely customer service.

The HR Generalist manages payroll records and reviews, employee onboarding, benefits administration, personnel records, employment documents, employee HR inquiries, performance management support, and HR compliance activities. The role partners with Finance and benefit providers, supports managers and employees, and maintains accurate HR systems and processes in a fast-paced SaaS startup environment.

Drive full-cycle enterprise sales from prospecting through close, develop account and territory plans, engage C-suite decision-makers, deliver strategic presentations and ROI analyses, navigate complex multi-stakeholder sales cycles, and partner cross-functionally to deliver tailored solutions. Build outbound pipeline, exceed revenue targets, advise enterprise clients, and provide market feedback to inform product and go-to-market strategies.

Serves as the company’s first point of contact by welcoming guests, directing calls, managing bookings and reminders, handling administrative tasks, distributing mail, and supporting meetings and events. Requires professional communication, strong organization, customer service experience, proficiency with office software, and the ability to prioritize tasks in a fast-paced environment. Standard business hours are required, with occasional weekend availability.

Co-found and help build Outpost, a pre-seed startup developing autonomous infrastructure for multi-OEM robotics environments. Founding team members will shape the technical vision, product, market, culture, and company category while addressing robotics infrastructure, continuous operations, and charging downtime. Opportunities span senior leadership, commercial, hardware engineering, and software engineering.

Schedule and publish pre-created social media posts across platforms, maintain content calendars, verify formatting and links, monitor scheduled posts, and support organized digital content workflows for multiple brands.

Identify and engage prospects through inbound and outbound sales efforts, conduct discovery calls, present solutions, manage pipeline opportunities, maintain accurate CRM records, follow up consistently, meet sales targets, and coordinate customer handoffs with internal teams.

Directs business development for enterprise and national accounts, driving revenue growth through prospecting, strategic relationship building, consultative selling, proposals, negotiations, and contract execution. Develops customized energy, infrastructure, and facility solutions, manages the sales pipeline, monitors market opportunities, collaborates across teams, and represents the company at industry events. The role requires executive-level communication, enterprise sales expertise, CRM proficiency, and up to 40% travel.