Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end UX for web and mobile products: create wireframes, prototypes, and high-fidelity designs; run user research and usability testing; maintain design systems; use data to drive decisions; collaborate with PMs and developers; and mentor junior designers to improve product experiences.

Configure and validate benefits system builds, review and QA data, follow enrollment and implementation process flows, document processes, collaborate with internal partners, track productivity, escalate issues, and participate in training on new functionality.

Drive pre-funnel and demand-generation programs to support B2B sales and channel partners. Create and execute multi-channel content and lead nurture strategies, manage partner engagement and events, track and report campaign performance, and collaborate cross-functionally to build pipeline and enable retention and advocacy.

Plan, manage, and execute virtual and in-person events and tradeshows to drive pipeline. Handle venue sourcing and contracts, speaker coordination, registration and event apps, hotel rooming, transportation, budgets, exhibitor/sponsor agreements, lead retrieval and reporting, swag/logistics, onsite event support, promotions, and website event updates. Collaborate with marketing, sales, and vendors to ensure creative, cost-effective, and well-run experiences.

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.

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.

Lead cross-functional CX teams to deliver and optimize benefits communication and engagement across a client book. Develop integrated communication strategies, monitor KPIs, manage escalations, identify upsell and renewal opportunities, enable best-practice adoption of tools (Sofia, MyChoice App), partner with sales/onboarding, and mentor staff to improve client retention and service delivery.

Lead client acquisition onboarding using agile/change management and work-management best practices. Create and maintain schedules, manage risks, drive task ownership, communicate status, validate AI-assisted outputs, produce documentation (SOPs, meeting notes, handoffs), track KPIs, support continuous improvement, and contribute to playbooks and team development to ensure timely, on-scope, high-quality project delivery.