Top Tech Jobs & Startup Jobs in Chicago, IL

Senior UX Designer responsible for researching complex enterprise workflows and designing clear, accessible AI product experiences. The role spans interaction and visual design, information architecture, prototyping, usability testing, design systems, interface writing, and post-release evaluation. The designer partners with Product, Engineering, Marketing, and customer teams to simplify workflows, establish reusable patterns, validate AI experiences, and improve product usability and adoption.

Provides senior legal counsel on complex commercial transactions, government contracts, vendor agreements, RFPs, procurement, compliance, and commercial risk. Leads contract negotiations, develops legal playbooks and policies, improves AI-assisted legal processes, trains business teams, and independently manages a high-volume portfolio of matters. Advises sales, procurement, operations, legal leadership, and senior stakeholders while managing and resolving cross-functional legal issues.

Own strategic enterprise accounts, driving retention, renewals, expansion, quota attainment, and revenue growth. Build account plans, cultivate executive relationships, lead business reviews, negotiate commercial agreements, manage forecasts and pipeline, identify risks and opportunities, and coordinate internal teams to deliver client value. Serve as a strategic advisor and advocate for major clients while sharing account-management best practices and supporting team development.

Leads relationship management and client engagement strategy across major financial institution accounts. Oversees relationship managers and client success teams, drives retention, portfolio revenue growth, renewals, and account expansion. Acts as an executive advisor to C-level stakeholders, aligns product and delivery teams, resolves strategic issues, and advocates for client needs in product and go-to-market planning. Requires extensive financial services, leadership, complex sales, and B2B SaaS client management experience.

Owns InvoiceCloud’s Insurance market strategy and serves as the market-facing authority for the P&C insurance vertical. Develops competitive and customer insights, translates them into product, roadmap, partnership, sales, and marketing recommendations, and influences senior stakeholders without P&L or quota ownership. Builds and explains shipped prototypes using current AI and prototyping tools, represents the company with customers and partners, and drives alignment across Product, Engineering, Sales, and Marketing.

Supports the SVP of Solution Consulting by managing complex calendars, meetings, travel, communications, confidential information, expenses, events, onboarding, and operational priorities. Coordinates cross-functional initiatives, tracks actions and dependencies, resolves scheduling conflicts, and supports organizational alignment. The role requires strong judgment, discretion, organization, communication, adaptability, and advanced proficiency with Microsoft Office and Adobe Acrobat.

Supervises and coaches collegiate chapters on recruitment activities, Panhellenic operations, NPC policies, recruitment planning, statistics, and continuous open bidding. Partners with chapter advisors, officers, regional teams, and recruitment leaders to improve recruitment outcomes, conduct chapter visits, interpret governing documents, and support strategic recruitment goals. This volunteer role requires approximately four to eight hours weekly, with peak periods of up to 20 hours and travel of up to nine days annually.

Part-time Junior Product Designer creating web-based UI/UX designs for a cyber operations platform. Responsibilities include gathering user needs, designing feature interfaces within an established design system, supporting product vision, presenting designs, incorporating feedback, suggesting legacy migrations, and conducting usability testing. The role requires collaboration with designers, engineers, and customers, plus responsive design experience and willingness to obtain a Top Secret clearance if requested.

Leads strategic customer programs across the Americas, coordinating cross-functional workstreams, customer workshops, partners, and internal teams from planning through production. Builds executive relationships, drives solution adoption and customer value, manages risks, budgets, timelines, and dependencies, and supports presales activities. The role requires strong consultative leadership, change management, communication, and experience delivering complex technology or cybersecurity projects. Travel up to 10% is required.

Own and optimize Workday Payroll and Core HCM, including configuration, security, business processes, reporting, integrations, governance, and system controls. Partner with People, Payroll, Finance, Accounting, Total Rewards, and IT to ensure accurate payroll and workforce data. Lead enhancements, releases, testing, troubleshooting, documentation, automation, and AI-enabled workflow improvements while supporting workforce planning and cross-functional system strategy.