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Assistant Trainer Jobs in Chicago, IL (NOW HIRING)

Wing Assistant

Sales Enablement Trainer

Chicago, IL · Remote

$29K - $35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team -- not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day.

Wing Assistant

Sales Enablement Trainer

Chicago, IL · On-site

$29K - $35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day.

Wing Assistant

Sales Enablement Trainer

Chicago, IL · On-site +1

$29K - $35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day.

A Knock At Midnight

Assistant IT Trainer

Chicago, IL · On-site

$30/hr

The Assistant IT Trainer must take a hands-on approach to improving digital literacy skills in young adults. The Assistant IT Trainer will play a key role in mentoring and helping young adults ...

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Assistant Trainer information

See Chicago, IL salary details

$16.5K

$43.3K

$72.1K

How much do assistant trainer jobs pay per year?

As of Aug 13, 2026, the average yearly pay for assistant trainer in Chicago, IL is $43,306.00, according to ZipRecruiter salary data. Most workers in this role earn between $24,700.00 and $52,000.00 per year, depending on experience, location, and employer.

What does an assistant trainer do?

An assistant trainer supports the lead trainer in delivering training sessions, preparing training materials, and managing logistics. They may also evaluate trainee progress, provide feedback, and help ensure training objectives are met, often requiring good communication skills and familiarity with training tools. The role typically involves working in educational or corporate environments and may require relevant certifications or experience in the subject area.

What are the key skills and qualifications needed to thrive as an assistant trainer?

To thrive as an Assistant Trainer, you need strong subject knowledge, basic instructional skills, and often a relevant degree or certification in the field of training. Familiarity with learning management systems (LMS), presentation software, and sometimes assessment tools is typically required. Excellent communication, adaptability, and teamwork are vital soft skills for effectively supporting lead trainers and engaging participants. These skills and qualifications are crucial to ensure effective learning experiences and smooth training program delivery.

What is an assistant trainer?

Assistant Trainers are professionals who support lead trainers in planning, organizing, and conducting training sessions for individuals or groups. They help prepare training materials, facilitate activities, and provide guidance and feedback to participants. Assistant Trainers often handle administrative tasks, monitor participant progress, and may step in to lead portions of training under supervision. Their role is crucial in ensuring the smooth delivery and effectiveness of training programs.

What are some typical challenges assistant trainers face when supporting training sessions?

Assistant Trainers often face the challenge of adapting to different learning styles within a group and ensuring all participants remain engaged. They may also need to manage logistical details, such as preparing materials and troubleshooting technical issues, all while supporting the lead trainer. Strong communication and flexibility are crucial, as Assistant Trainers frequently collaborate with both trainers and trainees to create a smooth, effective learning experience.

What is the difference between Assistant Trainer vs Trainer?

AspectAssistant TrainerTrainer
Required CredentialsCertifications in training or education, relevant experienceSame as Assistant Trainer, often with more experience
Work EnvironmentAssists in training sessions, supports trainersLeads training sessions, develops training materials
Employer & Industry UsageCommon in corporate, educational, fitness sectorsUsed across similar industries, often with more responsibility

The main difference between an Assistant Trainer and a Trainer is the level of responsibility. Assistant Trainers support and assist in training activities, while Trainers lead sessions and develop training content. Both roles require relevant certifications and experience, but Trainers typically have more expertise and autonomy.

What are the most commonly searched types of Trainer jobs in Chicago, IL?

The most popular types of Trainer jobs in Chicago, IL are:

What are popular job titles related to Assistant Trainer jobs in Chicago, IL?

For Assistant Trainer jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Assistant Trainer jobs in Chicago, IL look for?

The top searched job categories for Assistant Trainer jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Assistant Trainer jobs?

Cities near Chicago, IL with the most Assistant Trainer job openings:

Assistant Trainer jobs near you
Infographic showing various Assistant Trainer job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 77% Full Time, 19% Part Time, 1% Temporary, and 2% Contract. Highlights an 96% Physical, 2% Hybrid, and 2% Remote job distribution, with an average salary of $43,306 per year, or $20.8 per hour.

Sales Enablement Trainer

Wing Assistant

Chicago, IL • Remote

$29K - $35K/yr

Full-time

Re-posted 21 days ago

Job description

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team — not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day. This is a coach who has carried a quota and closed, and uses that credibility to make real, measurable improvements on the floor.

If your first instinct when a deal stalls is "let me see the thread and the call recording" — read on.

Responsibilities
  • Sit in the calls — live and recorded — and find exactly where deals are being lost.
  • Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works.
  • A/B test sales emails, call openers, demo pitches, and tactics like personalized video — keep the winners, kill the losers.
  • Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message.
  • Coach reps one-on-one on real calls and build the objection-handling playbook for our market — then drill it until it's reflexive.
  • Produce a video training series and self-serve modules with assessments, so new reps ramp fast and tenured reps keep sharpening.
Requirements

You'll thrive here if you

  • Have personally sold and closed — ideally outbound/high-volume B2B — and can show your numbers.
  • Write sales copy that converts and can explain why it works.
  • Are comfortable on camera and can produce clean training videos without a production team.
  • Can structure an A/B test, read the result honestly, and make the call.
  • Coach without crushing — you leave reps better and more confident.
  • Move fast: a diagnosis becomes a usable fix in hours, not weeks.
  • Know your way around a CRM (Hubspot plus) and a sales sequencing tool.

Nice to have

Experience in virtual staffing, BPO, or managed services · Pipedrive or CRM automations · video editing · sequencing tools (Apollo, Outreach, Salesloft, Instantly, Smartlead) · prior sales enablement assets (playbooks, battle cards, certification programs).

Why the Role

How the role actually runs — fast loop, not slow decks: Listen → Diagnose → Build → Intervene.

  • You hear the calls, name the specific problem, build the fix the same day, and get it into reps' hands immediately. A pattern that shows up Monday should have a tested correction in motion by midweek.

Why this role

  • You're joining at a build moment. You'll start lean and resourceful — and as the program proves it drives revenue, it ears more investment and room to grow. This is a roll-up-your-sleeves, multi-hat seat for someone who wants to own the engine, not manage a slide deck.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.