Sr. Specialist, Compliance Training

Insight Global; Chicago (IL); On-site; USD 90,000 - 125,000; Full time

Job summary

Insight Global is seeking a Senior Specialist, Compliance Training to lead enterprise-wide training programs that translate regulatory requirements into practical guidance. You will design, develop, and maintain engaging learning content across formats and ensure content remains aligned with source policies and audit-ready standards.

The role emphasizes partnership with Risk, Legal, HR, and Policy teams, with a focus on measuring program effectiveness and driving continuous improvement in

Qualifications

• 5+ years of experience in Compliance, policy content development, or learning & development within a financial services, exchange, or regulated environment.
• Demonstrated experience designing and delivering compliance training content.
• Proficiency with LMS platforms and content authoring tools (Articulate, Learn365).
• Analytical thinker and strong written and verbal communicator.

Responsibilities

• Design and manage the Compliance Training calendar with milestones and delivery timelines.
• Create and deliver engaging training content (e-learning, microlearning, job aids, assessments).
• Translate policies into clear learning experiences for diverse audiences.
• Write and edit training materials; ensure accuracy and sources are traceable.

Skills

Analytical thinking

Communication skills

Strong writing and verbal skills

Learning & development

Tools

Articulate

Learn365

Job description

Job Description

The Senior Specialist, Compliance Training is responsible for Cboe’s enterprise-wide Compliance Training program. You’ll design and deliver training that translates policies and requirements into clear, usable guidance, supporting a strong culture of compliance and ethics and enabling confident and informed decision making. The work is highly visible, impactful, and collaborative, offering the opportunity to see your efforts translate into stronger compliance outcomes across the organization.

Compliance Training Development & Maintenance

• Develop and manage the Compliance Training calendar, including expected deployment schedules and training development milestones, monitoring feedback and training development progress, and escalating when delivery milestones are at risk.
• Create and deliver engaging training content across multiple formats (e-learning, microlearning, job aids, assessments, and on-demand modules) tailored to diverse audiences and business needs, encompassing both scheduled and remedial training.
• Translate complex regulatory and policy requirements into clear, accessible learning experiences that support employee understanding and adherence to company obligations.
• Serve as primary writer and editor of all training materials, ensuring content is accurate, timely, and appropriately tailored to the topic and intended employee audience.
• Ensure all training content is traceable to source policies and is updated in response to organizational and policy changes.
• Identify gaps or enhancement opportunities, and implement improvements based on feedback and training program data.
• Maintain a centralized training content library and version-control process to ensure materials remain current, consistent, and audit-ready.

Stakeholder Engagement & Delivery

• Partner with Compliance, Policy Governance, Risk, Legal, HR, and other stakeholders to gather input, lead structured content reviews, incorporate feedback, and ensure training accuracy, relevance, and alignment with approved policies.
• Implement training delivery approaches that support effective employee learning and enable evaluation of program effectiveness.
• Communicate changes in training content and procedures to relevant parties and compose training-related distribution communications.
• Serve as the point of contact for Compliance Training questions across the organization.

Metrics & Reporting

• Collaborate with metrics team to:
  • Track, analyze, and report on training completion rates, assessment scores, and program effectiveness.
  • Develop dashboards and reporting mechanisms that provide leadership with visibility into training status and gaps.
  • Use data insights to drive continuous improvement in training content and delivery.

Technology & Infrastructure

• Manage the Compliance Training platform (LMS) and serve as the primary liaison with the supporting technology and HR teams.
• Evaluate and implement new training tools or delivery channels to improve reach and engagement.

Compliance Certification, Policy Alignment, & Other Duties

• Support the annual Compliance certification process.
• Develop and maintain Compliance Training-related policies, procedures, and job aids.
• Perform other duties as assigned.

Skills and Requirements

• 5+ years of relevant experience in Compliance, policy content development, or learning & development within a financial services, exchange, or regulated environment.
• Demonstrated experience designing and delivering compliance training content.
• Proficiency with LMS platforms and content authoring tools (e.g., Articulate, Learn365).
• Analytical thinker and strong written and verbal communicator

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal employment opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment without regard to race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request to [e-mail].