Top Tech Jobs & Startup Jobs in Chicago, IL

Own a portfolio of dealership clients, conducting consultative performance reviews, tracking KPIs, identifying operational gaps, improving platform adoption, mitigating churn risk, and supporting account expansion. The role requires strong automotive fixed-operations knowledge, analytical problem-solving, change-management expertise, and relationship-building skills to improve customer outcomes and revenue retention.

Build and maintain cloud-native microservices, APIs, event-driven workflows, and serverless applications using TypeScript and AWS. Integrate new services with legacy WordPress and PHP systems, support platform modernization, write specifications and automated tests, troubleshoot production issues, and improve infrastructure, observability, and reliability. Collaborate remotely with product, design, QA, and engineering teams while participating in code reviews and on-call support.

Owns Shipium’s automated carrier billing audit service, including product rules, client onboarding, escalations, carrier dispute standards, reconciliation workflows, and financial integrations. Leads Audit Advisors, ensures accurate discrepancy detection, GL coding, reporting, payment files, and dispute recovery, and partners with product and technology teams to increase automation. The role requires deep parcel or freight billing audit expertise, client-facing leadership, carrier invoice data experience, and team management.

Partners with Marketing and Customer Success Managers to identify opportunities, conduct consultative discovery, demonstrate AI and other solutions, and develop ROI-backed proposals. Qualifies and documents opportunities for CSM-led closing, ensures seamless customer handoffs, and shares customer and market insights with Marketing and Product. The role requires translating AI capabilities into business value, generating pipeline, and communicating effectively with technical and executive audiences.

Build and lead AI2IO’s product adoption and training discipline across applications and features. Establish standards for seminars, live training, videos, documentation, onboarding, UAT, release readiness, learning paths, and adoption measurement. Deliver high-impact training, coordinate with Product, Engineering, Customer Success, and support teams, and mentor contributors without formal management authority. Improve content governance, accessibility, self-service, rollout readiness, and ecosystem-wide adoption through evidence-based programs and AI-assisted content workflows.

Own relationships with employer clients, drive program adoption, report on value, manage escalations, secure renewals, and expand product usage. Build trusted partnerships, use data-driven insights to influence decisions, coordinate cross-functional resources, advocate for clients, and support enrollment campaigns. The role also includes coaching client success team members and contributing to evolving best practices.

Drive net-new business and account expansion among state, local, and education agencies. Own the full enterprise sales cycle, from prospecting and discovery through demonstrations, negotiations, and close. Build territory plans, exceed quota, lead value-based presentations, collaborate with internal teams, and represent Everlaw at conferences and customer meetings. The role requires monthly travel throughout the territory and experience selling enterprise SaaS or legal services to complex accounts or government agencies.

Own Compound Planning’s full content engine, including editorial strategy, writing, publishing, PR, social, product marketing, events, lifecycle email, agency management, and distribution. The role requires independently producing high-impact content, making final editorial decisions, coordinating advisors and partners, managing compliance workflows, improving content-to-pipeline handoffs, and scaling successful programs across channels.

Drive new business acquisition among enterprise eCommerce customers, build executive-level relationships, exceed revenue quotas, and close high-value SaaS opportunities. Apply expertise in post-purchase experiences, delivery protection, returns, order tracking, customer communications, and global supply chains. Manage consultative sales cycles involving enterprise deal sizes above $200,000 ARR while leveraging existing industry relationships and aligning solutions with complex client needs.

Own the platform foundations enabling secure data movement across Kodex, including identity, APIs, integrations, MCP servers, enclaves, encryption, and infrastructure. Lead KIP, API strategy, platform roadmaps, compliance readiness, and internal adoption. Partner closely with engineering and product leadership, translate customer needs into platform capabilities, and align cross-functional teams on priorities, architecture, and delivery.