Top Tech Jobs & Startup Jobs in Chicago, IL

Entry-level rotational actuarial program involving reserving, pricing, modeling, and analytics across personal and commercial insurance lines. Participants complete three 18-month rotations, receive technical training and mentoring, and develop skills for solving business problems involving risk and uncertainty. Candidates need a relevant bachelor’s degree, strong analytical and communication skills, leadership experience, commitment to the ACAS designation, and at least one passed actuarial exam.

Leads complex enterprise customer onboarding and SAP Spend and Invoice implementations, including ERP integrations, custom workflows, compliance frameworks, and platform configuration. Manages CFO-level stakeholders, IT teams, consultants, and internal implementation resources. Provides finance and compliance guidance, coordinates change management, drives adoption, mentors implementation staff, and contributes to global implementation methodology.

Supports go-to-market launches for FedNow product features by coordinating Product, Marketing, Sales, and Operations. Develops customer-focused messaging, launch plans, educational resources, webinars, training, and industry presentations. Tracks deadlines, researches customer personas and competitors, improves business-development processes, and ensures internal stakeholder readiness and consistent customer communications.

Administer and configure the commercial Salesforce org, including user access, automation, reports, dashboards, data integrity, territory alignment, integrations, sandboxes, and releases. Gather requirements, manage the Salesforce backlog, write user stories, coordinate engineering delivery, conduct UAT, provide field support and training, and improve commercial processes through automation and governance.

Provide first-level phone, email, and chat support to health insurance agents and clients. Triage and prioritize requests, resolve common contract and onboarding issues, document interactions in a ticketing system, escalate complex cases, gather feedback, and collaborate with internal teams to improve service delivery. This is a full-time contract role from late September through December 2026, with in-person Chicago training followed by fully remote work.

Leads a team providing advanced Tier 4/L3 support for enterprise applications. Responsibilities include resolving complex production issues, performing root-cause analysis, guiding software development and architecture, mentoring engineers, improving reliability and observability, designing automation, managing incidents, and partnering with development, infrastructure, security, and cloud teams across Microsoft and Azure environments.

Leads the enterprise Customer Success organization, managing multiple teams and people managers. Owns customer retention, expansion, adoption, advocacy, KPI achievement, executive relationships, escalations, and customer experience. Partners with Sales, Services, Product, and internal stakeholders to improve processes, develop talent, drive platform value, and achieve commercial outcomes across the assigned book of business.

Supervise an outbound collections team by managing performance metrics, quality assurance, coaching, training, and employee engagement. Conduct meetings and performance reviews, identify trends, recommend productivity improvements, and support hiring and onboarding. The role requires leadership experience, financial or loan operations knowledge, strong communication skills, and the ability to manage tense situations effectively.

Owns lifecycle email strategy and deployment for complex B2B marketing programs. Responsibilities include campaign architecture, audience segmentation, cadence planning, lifecycle copy, KPI definition, Marketo or Adobe Journey Optimizer deployment, testing, reporting, compliance, and AI-assisted personalization. The role partners cross-functionally with campaign, content, audience, analytics, and digital teams while managing governance, sequencing, and performance optimization across events, webinars, product launches, and multi-region programs.

Conduct risk-based penetration tests, assumed-breach exercises, adversary simulations, and purple-team engagements across enterprise systems, applications, networks, identity platforms, and cloud environments. Evaluate preventive, detective, and response controls, validate detection and incident-response effectiveness, and translate technical findings into risk-based remediation recommendations for technical teams, executives, Internal Audit, and the Audit Committee. Build an independent, continuously improving offensive-security assurance program.