Remote Instructor Jobs in Chicago, IL (NOW HIRING)

Job Description: Digital Accessibility Trainer / Instructor Company Promet Source — 4809 N. Ravenswood Ave., Suite 126, Chicago, IL 60640 Classification Contract — Independent Contractor (1099) Reports To Director of Accessibility Services / Senior Account Manager Delivery Mode In-Person (client site), Virtual (live online), or Hybrid Engagement Type Multi-client: deployed across successive and concurrent client engagements Commitment Part-time or full-time, depending on client pipeline volume Location Remote with travel to client sites as required (U.S.-based) Compensation Contract rate commensurate with experience; paid per engagement or retainer About Promet Source Promet Source is an award-winning, open-source design and development agency headquartered in Chicago. Founded in 2003, Promet specializes in accessible, standards-compliant digital solutions for government, higher education, healthcare, nonprofit, and association clients across the United States. Our accessibility practice is led by IAAP- and CPACC-certified professionals who conduct WCAG audits, remediation, consulting, and training. We combine automated and manual testing with deep assistive-technology expertise to help clients achieve and sustain ADA and Section 508 compliance. As the April 2026 and April 2027 DOJ Title II deadlines drive unprecedented demand for accessibility training among state and local governments, Promet is expanding its training delivery capacity. This contract position is designed to be deployed across multiple client engagements—not a single project. The successful candidate will become a core member of Promet’s accessibility training team, delivering our curriculum to cities, counties, special districts, universities, and other public-sector organizations on a recurring basis. Position Summary Promet Source is seeking a contract Digital Accessibility Trainer to deliver instructor-led and self-paced training programs that prepare client staff to create, publish, and maintain accessible digital content in compliance with ADA Title II and WCAG 2.1 Level AA. This is a multi-client, ongoing contract—not a single engagement. The trainer will be assigned to successive and, at times, concurrent client projects as Promet’s accessibility training practice grows. The trainer will deliver a comprehensive curriculum spanning accessible Word documents, PDF forms and documents, HTML web content, social media, multimedia and captioning, accessibility testing, vendor procurement, and governance. Training audiences will include content editors, web developers, communications staff, administrative personnel, department managers, and executive leadership across diverse public-sector organizations. Each engagement will be scoped and customized by Promet’s accessibility and account management team in collaboration with the trainer. The trainer is expected to adapt Promet’s base curriculum to each client’s CMS platform, document workflows, organizational structure, and regulatory timeline while maintaining consistent quality and brand standards. Essential Duties and ResponsibilitiesClient Training DeliveryDeliver Promet’s Digital Accessibility Training Curriculum to client staff through instructor-led sessions (in-person at client facilities and/or live virtual), covering modules on foundations, Word, PDF, HTML, social media, multimedia, testing, procurement, and governanceAdapt delivery to each client’s audience: hands-on workshops for content editors and developers, executive briefings for leadership, and role-specific deep dives for specialized staffCustomize training examples using each client’s actual web pages, documents, forms, CMS, and social media accounts rather than relying solely on generic samplesConduct live demonstrations of assistive technology (screen readers, keyboard navigation, magnification) to show participants how people with disabilities experience their contentAdminister module-level knowledge checks and practical assessments to verify applied competencyManage training logistics in coordination with Promet’s account management team, including scheduling across client departments, room/platform setup, and materials distributionCurriculum and Materials DevelopmentContribute to the ongoing development and refinement of Promet’s reusable training curriculum based on field experience, participant feedback, and evolving standards and regulationsDevelop and maintain supplemental materials: recorded video walkthroughs, step-by-step job aids, quick-reference cards, and practice exercises for self-paced learningCreate client-specific customizations (branded slide decks, exercises using client content, CMS-specific instructions) that can be templated for efficiency across similar engagementsDocument lessons learned and reusable patterns from each engagement to improve delivery quality for future clientsStay current with WCAG updates, DOJ guidance, assistive technology releases, and platform accessibility feature changes, and incorporate updates into curriculum materialsTechnical Instruction ScopeAccessible Microsoft Word documents: built-in styles, heading hierarchy, alt text, table structure, link text, color contrast, Accessibility Checker, and export to tagged PDFAccessible PDF creation and remediation: Adobe Acrobat Pro tagging, reading order, form field labeling, tab order, tooltips, bookmarks, and validation against WCAG criteriaAccessible HTML content: semantic structure, ARIA, keyboard and focus management, forms and error handling, color contrast, media alternatives, reflow, and text spacingAccessible social media: platform-native alt text, CamelCase hashtags, caption requirements, accessible graphics, and plain-language practicesAccessible multimedia: captioning workflows, transcript creation, audio description, SRT/VTT files, and accessible virtual meeting practicesAccessibility testing: automated scanners (axe, WAVE, Lighthouse), manual keyboard testing, screen reader spot-checking (NVDA, VoiceOver), color contrast tools, and document checkersClient Advisory SupportAdvise client teams on establishing digital accessibility policies, content publishing standards, and pre-publish checklists aligned with WCAG 2.1 AA and DOJ guidanceGuide client staff through legacy document triage (archive, remediate, replace with HTML, rebuild) using the DOJ’s exception criteriaReview vendor VPATs/ACRs and advise procurement staff on contract language for accessibility requirementsEscalate complex technical or legal questions to Promet’s senior accessibility consultants when issues exceed the training scopeReporting and Account SupportTrack training completion by department, role, and module for each client engagement, and deliver progress reports on Promet’s agreed cadenceProvide post-engagement summaries documenting training delivered, competency levels observed, remaining gaps, and recommendations for follow-on servicesSupport Promet’s business development by participating in pre-sales calls, scope definition, and proposal development when training expertise is needed to close an engagementRepresent Promet Source professionally in all client interactions, maintaining brand standards and client relationship quality Required QualificationsEducation and ExperienceMinimum 3 years of direct experience delivering digital accessibility training to adult learners in professional, government, or higher-education settingsMinimum 3 years of hands-on experience conducting WCAG-based accessibility audits, including both automated and manual testing with assistive technologyDemonstrated working knowledge of WCAG 2.1 Level AA success criteria, sufficient techniques, and common failures, with the ability to explain each in plain language to non-technical audiencesPractical experience creating and remediating accessible content in Microsoft Word, Adobe Acrobat Pro (PDF forms and documents), and HTML/CSS/ARIAExperience with at least two screen readers (e.g., NVDA, JAWS, VoiceOver, TalkBack) and the ability to demonstrate them live in a training settingTechnical KnowledgeThorough understanding of WCAG 2.1 and familiarity with WCAG 2.2, including the four POUR principles, conformance levels, and the conformance modelWorking knowledge of HTML5 semantic elements, ARIA roles/states/properties, CSS layout, and how these interact with assistive technologyProficiency with accessibility testing tools: axe DevTools, WAVE, Lighthouse, Colour Contrast Analyser, and Adobe Acrobat’s Accessibility CheckerAbility to evaluate PDF tag structure, reading order, form field associations, and document properties in Acrobat ProUnderstanding of social media platform accessibility features across major platforms (Facebook, Instagram, X/Twitter, YouTube, LinkedIn)Familiarity with captioning workflows, SRT/VTT file formats, and live captioning in Zoom and Microsoft TeamsLegal and Regulatory KnowledgeUnderstanding of ADA Title II as it applies to state and local government digital content, including the 2024 DOJ final rule, the Small Entity Compliance Guide, and DOJ’s First Steps resourceUnderstanding of ADA Title III and Section 508 requirements as they apply to Promet’s private-sector and federal clientsAbility to accurately distinguish between legal requirements (WCAG 2.1 AA under DOJ rule), recommended best practices (WCAG 2.2), and general ADA obligations (effective communication, equal access) — and to explain those distinctions clearly to clients without overclaiming or underrepresenting riskAwareness of ongoing regulatory developments, including the DOJ Interim Final Rule under OIRA review and state-level accessibility laws (California Unruh Act, Colorado HB 21-1110, etc.)Training, Communication, and Client SkillsDemonstrated ability to teach complex technical material to non-technical audiences using plain language, practical examples, and hands-on exercisesExperience designing and delivering training in multiple formats: in-person workshops, live virtual sessions, recorded video tutorials, and written job aidsStrong facilitation skills with the ability to manage diverse classroom dynamics across varying technical backgrounds and comfort levelsProfessional client-facing demeanor with the ability to represent Promet Source as a trusted advisor; comfortable interacting with elected officials, city managers, IT directors, and frontline staffExcellent written communication skills for developing training materials, quick-reference guides, client reports, and assessment instrumentsCultural competence and sensitivity when discussing disability, assistive technology, and the experiences of people with disabilitiesSelf-directed work style: able to manage a personal schedule across multiple concurrent client engagements, meet deadlines, and communicate proactively with Promet’s project management team Preferred QualificationsCurrent IAAP certification: Certified Professional in Accessibility Core Competencies (CPAC), Certified Professional in Web Accessibility (CPWA), or Web Accessibility Specialist (WAS)DHS Trusted Tester certification or equivalent Section 508 testing credentialPrior experience training state or local government staff (cities, counties, special districts, public universities)Experience with Drupal, WordPress, or other CMS platforms commonly used in government and higher educationExperience developing or contributing to organizational accessibility policies and governance frameworksExperience with large-scale PDF remediation projects and document management system accessibilityFamiliarity with Promet Source’s service offerings, including Provus® products, accessibility audit methodology, and ADA consulting practiceLived experience with disability or direct professional collaboration with people who use assistive technology dailyBilingual communication skills (especially English/Spanish) are a plus Typical Client Engagement Model Each client engagement follows a structure defined by Promet’s account management and accessibility teams. The trainer participates in all phases and should expect to manage multiple engagements at various stages simultaneously.Phase 1: Scoping and Customization (1–2 Weeks per Client)Join kickoff call with Promet account manager and client stakeholders to understand organizational structure, CMS platform, document workflows, and compliance timelineCustomize curriculum examples and exercises using client’s actual content, forms, and web pagesFinalize training schedule, delivery format, and logistics with Promet project coordinatorPhase 2: Core Training Delivery (4–12 Weeks per Client)Deliver curriculum modules to targeted staff groups on a rolling scheduleConduct hands-on workshops, live demonstrations, and real-time exercisesProvide office-hours or drop-in support for staff completing self-paced modulesAdminister assessments and report interim progress to Promet and client leadershipPhase 3: Handoff and Follow-On (1–2 Weeks per Client)Deliver final materials, job aids, and checklistsSubmit post-engagement report with competency benchmarks, gap analysis, and recommendationsBrief Promet account team on follow-on opportunities (refresher training, advanced topics, new-hire onboarding, audit services, remediation projects) Promet anticipates a steady pipeline of client engagements, particularly among state and local governments preparing for the DOJ Title II deadlines. The trainer should expect to ramp up from one concurrent engagement to two or three as the practice scales. Deliverables per Client EngagementTraining sessions: Instructor-led delivery of all assigned curriculum modules, scheduled across client departments within the agreed timelineSelf-paced materials: Recorded walkthroughs, written guides, and practice exercises customized to the client’s tools and content typesQuick-reference job aids: One- to two-page desk references for each content type (Word, PDF, HTML, social media, multimedia)Knowledge assessments: Module-level quizzes and practical skill checks to verify comprehension and applied competencyCompletion tracking: Training log or dashboard showing completion status by department, role, and modulePre-publish checklists: Departmental checklists embedding accessibility checks into routine content workflowsPolicy recommendations: Written memo recommending components of a client accessibility policy, procurement language, content standards, and monitoring planEngagement report: End-of-engagement summary documenting training delivered, competency levels, gaps, and recommendations for sustained compliance and follow-on Promet services Contributions to Promet’s Accessibility Training Practice Beyond individual client work, the trainer is expected to contribute to the growth and quality of Promet’s training offering as a service line:Refine and improve the base curriculum after each engagement based on participant feedback and observed gapsBuild a library of reusable, templatized training assets (slide decks, exercises, job