Top Tech Jobs & Startup Jobs in Chicago, IL

Software Engineer Intern supporting the development of AI-powered educational assessment products. Responsibilities include building LLM and generative AI features, designing prompts, integrating tools, developing basic agent orchestration, evaluating AI systems for quality and safety, and collaborating with engineering, product, and research teams. The intern will gain experience designing, testing, and deploying production AI systems in an education technology environment.

Lead CFGI’s Complex Securities Valuation practice, serving as senior advisor on sophisticated financial-instrument and equity valuation engagements. Oversee methodologies, models, teams, quality, budgets, timelines, and client delivery while advising executives, boards, auditors, and finance leaders. Build strategic client relationships, drive business development, mentor senior professionals, and contribute to practice growth, technical guidance, recruiting, and thought leadership.

Supports DIRECTV for Business marketing through market research, customer and competitive analysis, event planning, lead tracking, Salesforce data management, and sales opportunity research. The intern may develop customer communications, research target accounts, identify trends, support event outreach, and help expand services within existing enterprise customers. This is a 10-week remote internship requiring strong communication, organization, collaboration, presentation, and Microsoft Office and Salesforce skills.

Recruit, onboard, match, monitor, and support technical mentors overseeing student open-source software projects. Responsibilities include mentor calls, reviewing weekly reflections, tracking team meetings, checking in with mentors, escalating concerns, and optionally recruiting volunteer mentors through outreach to technology companies. The role is contractor-based, flexible, fully online, and requires availability during some US working hours.

Design and implement a responsive landing page for an open-source web application. The contributor will translate design concepts into production-ready front-end code, use prototyping tools, consider web performance and Core Web Vitals, and work independently in a flexible, collaborative, project-based environment. This is a fully remote, voluntary, unpaid learning opportunity focused on building portfolio experience.

Manage and support a portfolio of client accounts, strengthening retention, satisfaction, service delivery, renewals, and growth opportunities. Coordinate onboarding, client communications, QBRs, issue resolution, billing reviews, contracts, CRM records, account metrics, and cross-functional delivery across HR, payroll, finance, compliance, and Employer of Record services. Support proposals, upselling, process improvements, and global stakeholder collaboration.

Manages Enterprise Health software deployments from pre-sale through go-live. Responsibilities include stakeholder alignment, project governance, scheduling, scope and change control, documentation, progress tracking, budget and timeline management, issue resolution, project closure, and process improvement. The role requires coordinating internal and external stakeholders, translating customer requirements into project specifications, supporting pre-sales activities, and traveling up to 20%.

Perform independent actuarial analysis supporting Pension Risk Transfer pricing. Responsibilities include coding and executing proprietary pricing models, recalculating premiums, maintaining and improving processes, calculating complex participant benefits, reviewing standard calculations, drafting contract language, and supporting special projects. The role requires collaboration, technical communication, attention to detail, and continued actuarial accreditation.

Own and improve Azure infrastructure while leading complex integrations, automation workflows, and cross-system implementations. Provide advanced escalation support for service desk issues, including SharePoint; diagnose interconnected platform problems; strengthen security, access controls, and system reliability; and maintain technical documentation. The role also supports internally developed applications, uses AI-assisted tools, and mentors engineers on engineering standards, testing, version control, and change management.

Manage a portfolio of enterprise SaaS customers to drive retention, renewals, and expansion. Coordinate cross-functional teams, define success metrics, drive product adoption and enablement, surface voice-of-customer insights, manage escalations and commercial negotiations, and maintain CRM records to ensure scalable, high-touch account success.