M365 CoPilot Trainer

Description
M365 Copilot Adoption & Enablement Lead
Location: Chicago, IL (Hybrid - downtown office ~2 days/week)
Overview
We're looking for a highly engaging, execution-oriented leader to drive the enterprise rollout of Microsoft 365 Copilot to a population of ~5,000-6,000 employees. This role focuses on training delivery, change activation, and executive enablement, bringing an established adoption program to life at scale.
What You'll Do
Deliver enterprise-wide and department-specific M365 Copilot training (including webinars up to 1,000+ attendees)
Facilitate executive-level and VP-partnered sessions to upskill leaders and their teams in AI
Tailor training content to department workflows and business needs
Host engaging learning experiences (prompt-athons, workshops, hands-on labs)
Execute change management and adoption activities using existing program assets
Coordinate Microsoft ESI training offerings and ensure attendance commitments
Partner with internal AI teams to roll out new capabilities and related training
What We're Looking For
Proven enterprise-level M365 Copilot training/rollout experience (Copilot Web included)
Exceptional facilitator with executive presence and "room-commanding" energy
Highly personable, charismatic, and credible with senior leaders
Execution-focused and comfortable operating in complex environments
Ability to translate AI concepts into practical, role-based use cases
Why This Role
High visibility and direct executive interaction
Large-scale impact on how the organization adopts AI
Focused on delivery-not program design
Additional Skills & Qualifications
onsite 2x/week
Experience Level
Expert Level
Job Type & Location
This is a Contract position based out of Chicago, IL.
Pay and Benefits
The pay range for this position is $20.00 - $65.00/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)
Workplace Type
This is a hybrid position in Chicago,IL.
Application Deadline
This position is anticipated to close on Jan 28, 2026.
>About TEKsystems:
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.

About TEKsystems and TEKsystems Global Services

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.