Top Tech Jobs & Startup Jobs in Chicago, IL

Run complex enterprise sales cycles from prospecting through close, manage a book of business, engage technical and executive stakeholders, drive customer adoption, refine sales processes, represent customer needs in product discussions, mentor Account Executives, and partner with marketing. The role requires enterprise B2B SaaS sales experience, preferably selling developer tools or similarly technical products, strong quota performance, technical acumen, and startup adaptability.

Manage a caseload of litigated claims, develop defense strategies, attend depositions, hearings, and mediations, analyze discovery and medical records, research legal issues, investigate parties and worksites, and draft briefs, memoranda, and client updates. The role requires substantial deposition experience, Illinois bar licensure, strong organizational skills, deadline management, independent judgment, and effective teamwork. Toxic tort experience is preferred, and applicants must submit a writing sample.

The Director will advise executives and people leaders while building leadership development, learning, performance management, employee relations, organizational effectiveness, and change-management programs. Responsibilities include coaching leaders, developing HRBP frameworks, supporting workforce planning and organizational design, guiding succession and talent decisions, using people data to identify risks, and leading cross-functional initiatives that improve culture, employee experience, leadership effectiveness, and organizational performance.

Performs insurance, third-party administrator, reinsurance, and mortgage investment accounting. Responsibilities include journal entries, general ledger reconciliations, financial statement analysis, regulatory and audit schedules, treaty review, reporting, and process improvements. Collaborates with IT, Actuarial, Legal, and other departments on accounting initiatives and system enhancements.

Designs, configures, implements, tests, and analyzes o9 supply chain planning solutions. Partners with clients and internal teams to gather requirements, transform business logic into technical designs, build datasets, perform forecasting and optimization, execute testing, resolve solution gaps, and support deployment. Delivers stakeholder training, communicates project progress, mentors junior analysts, and contributes to full lifecycle enterprise implementations.

Paid 10-week internship introducing rising seniors and graduate students to sales and client management in the employee benefits insurance industry. Interns will explore prospecting, quoting, selling, enrollment, onboarding, and relationship management; complete assigned business projects, job shadows, workshops, networking, and a capstone presentation. The role requires approximately 40 hours per week during regular business hours.

Design, develop, optimize, and deploy scalable computer vision and vision-language systems using classical computer vision and deep learning. Build evaluation frameworks, monitor production models, debug issues, and improve architectures with new data. Collaborate with product managers and cross-functional teams to deliver practical AI solutions across cloud and edge environments.

Create, edit, optimize, and publish web, lifecycle, vendor, organic, and paid marketing content across multiple brands. Write copy for blogs, landing pages, emails, campaigns, social, video, and webinar recaps while maintaining brand voice. Coordinate SME and Compliance reviews, apply SEO and GEO principles, publish through a CMS, and support customer journeys, discoverability, conversion, and brand trust.

Supervise and review employee benefits actuarial projects, including pension funding valuations, government filings, benefit calculations, and nondiscrimination testing. Manage project staff, budgets, and deadlines while leading actuarial analysts. Advise clients on project implications and solutions, deliver presentations, and foster team development. The role requires extensive multiemployer pension consulting experience, strong technical modeling abilities, and familiarity with ProVal.

Manage customer accounts, orders, and quote requests across multiple channels while supporting the sales process, identifying upsell opportunities, resolving issues, and building customer relationships. The role works with varied account levels and contributes to team goals in a fast-paced industrial distribution environment.