Entry Level Remote Empathetic Listener Jobs in Chicago, IL

Entry Level Insurance Sales Representative (100% Remote)

100% Remote | United States & Canada | Full-Time | Training Provided | Weekly Pay

A Sales Career You Can Grow Into

You don't need years of sales experience to build a career in insurance.

What you do need is the ability to listen, communicate clearly, learn new information, and genuinely care about helping people make informed decisions.

AO Globe Life is looking for Entry Level Insurance Sales Representatives to join our growing remote team. In this role, you'll speak with clients who have requested information, learn about their needs, explain available insurance and benefit options, and help them move forward with the coverage that fits their situation.

You'll receive training and ongoing coaching as you learn the products, systems, and sales process.

What Your Day Could Look Like

You'll spend your day having meaningful conversations with people rather than sitting through repetitive tasks.

Your responsibilities may include:

• Speaking with clients through scheduled phone or virtual appointments
• Asking questions to understand their needs and priorities
• Explaining insurance and benefit options in a simple, easy-to-understand way
• Answering client questions and providing accurate information
• Guiding clients through the application and enrollment process
• Following up with clients when appropriate
• Keeping client and application information organized and up to date
• Attending virtual training, team meetings, and coaching sessions
• Building your product knowledge and improving your sales skills over time

No cold calling is required. You will primarily speak with individuals who have already expressed interest in receiving information.

Why People Choose This Type of Career

Working remotely is only part of the opportunity.

This role can give you the chance to develop skills that can continue to pay off throughout your career.

You'll have access to:

• Qualified leads — connect with people who have requested information
• Structured training — learn the role step by step
• Ongoing coaching — receive feedback and support as you improve
• Remote work — work from your own home workspace
• Flexible scheduling — work within an agreed schedule
• No cold calling — focus on conversations with interested clients
• Weekly commission based — compensation is based on sales performance
• Growth opportunities — strong performers may have opportunities to take on additional responsibilities

You Might Be a Great Fit If...

You don't have to consider yourself a "salesperson" to apply.

This position may be a good fit if you:

• Enjoy talking with different types of people
• Can listen carefully and ask thoughtful questions
• Explain information clearly and confidently
• Are motivated by goals and measurable results
• Take responsibility for your work
• Can stay organized while working independently
• Are comfortable learning new technology and virtual systems
• Welcome coaching and are willing to improve
• Have experience in customer service, retail, hospitality, sales, recruiting, education, or another people-focused role, helpful, but not required

What We Want You to Know

Training and support are provided, but success in the role requires consistency, communication skills, follow-through, and a willingness to learn.

Start Where You Are. Build From There.

Your first sales conversation may feel very different from your tenth.

Over time, you'll have the opportunity to become more confident communicating with clients, handling questions, presenting information, managing your time, and closing business.

Those are skills you can take with you far beyond your first year.

About AO Globe Life

AO Globe Life provides remote insurance and benefit-related opportunities focused on helping clients understand their available options. Our team supports representatives through training, coaching, and continued professional development.

Ready to Take the Next Step?

If you're looking for a remote sales opportunity where you can learn a new industry, work directly with clients, and build skills through real experience, we'd like to hear from you.

Apply today to be considered for the Entry Level Insurance Sales Representative position.