Remote Insurance Instructor Jobs in Chicago, IL (NOW HIRING)

Overview

A Fortune 150 Healthcare Organization is seeking a highly skilled Adobe Express Trainer to support a global rollout of Adobe Express across marketing teams. This role is ideal for a confident, engaging facilitator who excels at delivering live virtual training and simplifying complex tools into easy-to-understand learning experiences.

You will serve as the face of training—leading live sessions, hosting office hours, and creating simple, highly effective training materials that empower users to confidently adopt Adobe Express.

Key Responsibilities

• Deliver engaging, instructor-led virtual training sessions to global marketing teams
• Host daily office hours to provide hands-on support and answer user questions
• Create clear, concise PowerPoint training materials that simplify workflows and concepts
• Teach best practices for Adobe Express and empower adoption across teams
• Adapt training delivery style to diverse audiences and skill levels
• Collaborate with marketing, creative, and program stakeholders to align training with business needs
• Manage your own training schedule and delivery approach with a high level of autonomy
• Continuously gather feedback and refine training content to improve learner outcomes

Required Skills & Experience

• Expert-level proficiency in Adobe Express
• Strong working knowledge of Adobe Creative Suite (Photoshop, Illustrator, etc. preferred)
• Proven experience delivering live virtual training to large and diverse audiences
• Exceptional facilitation and presentation skills — clear, confident, and engaging
• Advanced PowerPoint skills with ability to create clean, intuitive training materials
• Strong communication and interpersonal skills
• Ability to work independently and manage multiple training sessions
• Experience collaborating with cross-functional teams, especially marketing or creative

Preferred Qualifications

• Adobe certifications
• Experience training global or enterprise teams
• Background working in fast-paced, complex organizations
• Familiarity with change management or software adoption initiatives

Work Environment

• Fully remote
• Global, fast-paced, and highly collaborative environment
• Requires flexibility to support teams across multiple regions and time zones

Why Join

• Opportunity to support a high-visibility global rollout at a Fortune 150 company
• High-impact role driving adoption of a key creative platform
• Autonomy to shape training delivery and engagement strategy
• Work with global marketing and creative teams

What Success Looks Like

• High engagement and adoption of Adobe Express across teams
• Positive feedback from training participants
• Clear, scalable training materials that enable self-sufficiency
• Ability to simplify complex tools into accessible learning experiences

 Expert Level

This is a Contract position based out of Chicago, IL.

The pay range for this position is $80.00 - $90.00/hr.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following:
• Medical, dental & vision
• Critical Illness, Accident, and Hospital
• 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available
• Life Insurance (Voluntary Life & AD&D for the employee and dependents)
• Short and long-term disability
• Health Spending Account (HSA)
• Transportation benefits
• Employee Assistance Program
• Time Off/Leave (PTO, Vacation or Sick Leave)

This is a fully remote position.

This position is anticipated to close on Jun 4, 2026.

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.