Top Tech Jobs & Startup Jobs in Chicago, IL

Own relationships across a portfolio of higher-education accounts, manage renewals and account health, identify growth opportunities, and coordinate with Sales, Customer Success, Support, Marketing, and Product. Maintain account plans, CRM data, and forecasts while gathering customer feedback and supporting adoption and value realization. The remote role covers Kansas City, Missouri, Chicago, Madison, Milwaukee, Minnesota, and Iowa.

Design marketing campaigns and brand assets across digital, social, video, print, merchandise, and packaging channels. Maintain brand guidelines, photograph products, create motion graphics and video overlays, manage digital assets, prepare print-ready files, and update promotional decks and databases. Collaborate with editorial, marketing, art, and external partners to develop visual concepts and execute product and promotional materials.

Develops educator engagement strategies for new and early-lifecycle high school products. Builds relationships with educators and districts, gathers market insights, identifies launch barriers, supports paid pilots and early adopters, validates marketing messaging, and provides recommendations to Product, Sales, Marketing, and leadership. Tracks market-readiness indicators and helps create scalable educator engagement frameworks.

Owns organizational benefits strategy, plan design, vendor relationships, compliance, executive reporting, and team oversight. Manages benefits staff, escalated issues, vendor selection and negotiations, retirement plan governance, automation initiatives, and open enrollment or wellness programs. Advises leadership on regulatory risk, develops repeatable processes, and ensures accurate, responsive benefits administration.

Supports custom publishing projects by formatting manuscripts, preparing front matter and tables of contents, proofreading materials, researching photos, tracking permissions, maintaining Jira tickets, testing ePub files, compiling PDF eBooks, creating assessment content, reviewing courseware, and updating project documentation. The role requires strong organization, attention to detail, communication, deadline management, and proficiency with office, collaboration, and PDF tools.

Supports content workflow operations through file fulfillment, vendor coordination, DAM archiving quality control, copyright registration tracking, CMS collection management, and data retrieval. The contractor maintains accurate records, reports, errata documentation, litigation-related research packages, and deposit copy tracking while handling confidential materials and coordinating with internal stakeholders and external vendors.

Supports in-house employment counsel with workplace compliance, policy and agreement drafting, subpoenas, litigation and e-discovery, internal investigations, worker classification reviews, and legal research. Coordinates employment claims, agency inquiries, document collections, redactions, litigation holds, and compliance documentation across jurisdictions.

Coordinate production workflows for self-paced online learning courses across content, rights, marketing, platform teams, vendors, and partners. Manage Jira boards, timelines, task tracking, content handoffs, meetings, documentation, vendor onboarding, and status reporting. Identify workflow blockers, recommend process improvements, and support automation initiatives to maintain operational continuity throughout the pilot program.

Own and close small-revenue sales opportunities from qualification through execution. Develop personalized multi-channel outreach, maintain active prospect relationships, and partner with senior sales representatives, marketing, and sales operations. Use generative AI, CRM data, and modern sales tools to identify pipeline opportunities, test outbound tactics, maintain accurate Salesforce records, review pipeline health, and direct contractors as needed.

Drive the full engagement cycle for an AI-powered EdTech simulation platform, including prospect research, outbound outreach, consultative discovery, product demonstrations, instructor onboarding, pilot activation, adoption monitoring, feedback synthesis, and Salesforce reporting. The contractor will build higher education pilot opportunities, support classroom implementation, identify adoption barriers, document market insights, and develop continuation and advocacy plans.