Top Tech Jobs & Startup Jobs in Chicago, IL

Provide Linux system administration and Tier II support, manage AWS cloud infrastructure, automate provisioning and CI/CD, implement monitoring/alerting, configure DNS and web servers, use scripting (Python/Bash) and IaC tools (GitLab, Terraform, CDK), and support container orchestration (ECS/Kubernetes).

Serve as the primary day-to-day client contact for benefits administration clients, manage client communications, training, documentation, and annual enrollment activities. Coordinate internal teams, drive service quality improvements, support sales activities, and provide consultative guidance on product updates and system functionality to ensure client satisfaction.

Produce branded print, digital, and web employee-communication materials (benefit guides, emails, postcards, landing pages). Configure online portals, manage Adobe client libraries, collaborate with writers and clients on creative strategy, meet project deadlines, prepare files for fulfillment, and support consumer experience initiatives in a fast-paced environment.

Drive new business for MyChoice Accounts (consumer spending accounts) by selling to large employers (8,000+ lives). Build broker/partner relationships, manage full sales cycle, maintain pipeline and CRM records, present platform capabilities, attend industry events, and collaborate with sales support and marketing to exceed revenue targets.

Drive full sales cycle for Businessolver's SaaS benefits platform: prospect and cold-call enterprise employers, demo product, engage brokers and partners, build pipeline, close deals, coordinate with implementation, track activity, and attend marketing events and trade shows (travel up to 25%).

Implement and manage full lifecycle client data integrations for inbound HRIS and benefits conversion files. Gather requirements, configure files, establish secure transfers, oversee testing, coordinate clients/vendors, track project status, and transition integrations to steady-state while ensuring data accuracy and resolving defects.