Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Outside Sales Representative (Training Provided)

$75k

PLATINUM SUPPLEMENTAL INSURANCE

What if your income had no ceiling, your weekends were always free, and you had a proven system backing you up from day one?

At Platinum Supplemental Insurance, we've helped thousands of sales professionals build rewarding, high-earning careers—whether they came from sales, customer service, teaching, the military, or had no prior experience at all. Our established systems, AI-powered training, and dedicated back-office support mean you're never figuring it out alone. You bring the work ethic; we bring everything else.

No insurance experience required. We'll train you, license you, and pay you while you learn.

Why Platinum?

Your Weekends, Every Weekend

Work Monday through Thursday meeting with business owners and families in your territory, then enjoy a true three-day weekend—every single week. No evenings. No Saturdays. A work-life balance that actually works.

Earn What You're Worth—and Then Some

Our first-year sales consultants typically earn $75,000 or more, with top performers exceeding $100,000. Your effort directly drives your income, and there is no ceiling on what you can earn. Here's the full picture:

  • Strong First-Year Income: $75,000+ is typical; $100,000+ is achievable for motivated individuals.
  • Residual Renewal Income: Earn ongoing annual income from policies you've already sold—your book of business grows with you year after year.
  • Performance Bonuses: Generous bonuses reward your consistency and results.
  • Luxury Travel Incentives: Earn all-expenses-paid trips for you and a guest—quarterly getaways and annual destinations.

This is a commission-based position—your income is directly tied to your performance, not someone else's budget. Many of our top consultants say it's the first time they've truly been paid what they're worth.

Paid Training & Real Support From Day One

We don't hand you a manual and wish you luck. Platinum invests in every new hire with a structured onboarding program designed to set you up to succeed:

  • Licensing Assistance: We provide online training to help you earn your insurance license before you ever go to the field.
  • One Week of Paid Training: Before your first day in the field, you'll complete a full week of paid training—live webinars, sales training with experienced coaches, AI-powered virtual role-playing, and hands-on practice with our proven sales system.
  • Paid From Day One in the Field: Show up on your first Monday, get paid. Come back after your second week, get paid again. We put money in your pocket while you're building your business.
  • AI-Powered Coaching: Get personalized feedback, interactive coaching, and real-time support that helps you master our 10-step sales process faster and more confidently than traditional training.
  • Ongoing Back-Office Support: Marketing, lead generation, customer service, and operations are handled for you so you can focus on building relationships and closing deals.

Your Day-to-Day

Meet with Business Owners & Families: Travel within your territory Monday–Thursday to connect face-to-face with people who need supplemental insurance protection. You'll educate them on how Platinum's products bridge the gaps in traditional health coverage.

Follow a Proven Sales Process: Use Platinum's 10-step system—backed by AI coaching—to identify prospects, deliver compelling presentations, and close with confidence.

Grow Within a Supportive Team: Collaborate with a team that shares best practices, celebrates wins, and pushes everyone to get better. You'll have mentors and peers invested in your success.

What You'll Enjoy

Uncapped Income: Your earnings grow with your effort—no salary ceiling, ever.

Residual Income That Builds Over Time: Annual renewal commissions create a growing income stream from your existing book of business.

Every Weekend Off: A Monday–Thursday schedule means three-day weekends, every week.

Paid Training & Licensing Support: We invest in your professional development from day one.

Career Advancement: Move into leadership roles as you grow—Platinum promotes from within.

All-Expenses-Paid Trips: Quarterly getaways and annual vacations for top performers—bring a significant other, on us.

Who Succeeds at Platinum

People Who Want to Control Their Income: You're motivated by results and want your paycheck to reflect your effort, not a corporate pay scale.

Strong Communicators: You connect easily with people from all walks of life and can explain things in a clear, relatable way.

Coachable Self-Starters: You're excited to follow a proven system, learn from AI-powered training and experienced mentors, and improve every week.

Comfortable with Travel: You're 18+ and ready for overnight travel Monday–Thursday within your assigned territory.

What Happens After You Apply

We don't believe in leaving you in the dark. Here's exactly what to expect:

1. Apply & Chat: Submit your application right here and have a quick conversation with our hiring assistant. It takes just a few minutes.

2. Schedule Your Interview: If you qualify, you'll be able to schedule your first interview right away—most candidates have an interview on the books within 48 hours.

3. Meet Our Team: Talk to a real recruiter who'll answer your questions, share what the role looks like day-to-day, and see if it's a mutual fit.

4. Get Hired & Start Training: If we're both excited, you'll begin your licensing and paid training program—designed to get you earning as quickly as possible.

Ready to Build Something That Lasts?

If you want uncapped income, a four-day workweek, paid training, and the backing of a company that's invested in your success, we'd love to talk. Apply today and find out how Platinum can help you build a career you're proud of.

About Platinum

Platinum Supplemental Insurance helps individuals, families, and businesses protect their financial futures by bridging the gaps left by traditional health plans. When unexpected health issues arise, our products provide peace of mind and real financial protection. With a people-first culture, industry-leading AI training, and a commitment to the growth of every team member, Platinum is where driven professionals build lasting, lucrative careers—no matter where they're starting from.

Join Platinum and see why thousands of sales professionals have built careers they love.

Vacancy posted 2 hours ago
Similar jobs that could be interesting for youBased on the Outside Sales Representative (Training Provided) in Oak Park, IL vacancy
  • $50.5k - $70k

     ...Forward Join Snap-on as a Route Sales Representative! Are you ready to sell...  ...to shop, selling tools and providing hands-on demos Develop...  ...career in sales with full training provided Earn a competitive...  ...experience, preferably in outside sales, account management... 
    Training courses

    Snap-on

    Oak Park, IL
    4 days ago
  •  ...with a friendly, professional, low-pressure approach. This is a full-time position with excellent benefits. Sales experience is a plus, but training is provided - both in-house and off-site by our training team and our manufacturers. You will be trained to present and... 
    Training courses
    Full time

    McGrath Imports Parent

    Elmwood Park, IL
    1 day ago
  •  ...PeakForce is a fast-paced sales and marketing firm located in...  ...hiring Entry Level B2B Sales Representatives who will represent AT&T. We...  ...and management Hands-on training in sales, communication, and...  ...experience required (full training provided) If you’re ready to join a... 
    Training courses

    PEAKFORCE INC

    Chicago, IL
    19 days ago
  •  ...Marketing has immediate openings for sales rep positions, start work within the...  ...Previous experience isn’t necessary, we provide all the training needed for success. Position...  ...length of service or annual resets. Representatives are paid a base (25.00 base-appt) or... 
    Training courses
    Weekly pay
    Full time
    Part time
    Work experience placement
    Internship
    Work at office
    Immediate start
    Flexible hours

    Vector Marketing

    Oak Brook, IL
    13 days ago
  • $200k

     ...Launch Your Sales Career with Pre-Qualified Leads and Six-Figure Potential...  ...efficient windows and doors Provide professional quotes and close the sale Represent our brand with integrity and...  ...advancement based on results Paid Training Provided We give you the tools... 
    Training courses
    Full time
    Work at office

    Florida Window and Door

    Lombard, IL
    3 days ago
  •  ...Job Description PeakForce is a growing sales and marketing firm based in Chicago....  ...currently seeking an Entry-Level B2B Sales Representative to join our team. In this role, you...  ...entry-level position with structured training provided. No prior sales experience is required... 
    Training courses
    Work experience placement
    Work at office
    Local area

    Lively Management LLC

    Villa Park, IL
    3 days ago
  • $80k - $120k

     ...Outside Sales Representative B2B Sales Focus Inc. is hiring Outside Sales Representative - B2B to sell short term luggage storage systems...  ...transportation No prior sales experience required. Training provided. What We Offer: ~ Competitive Base + Uncapped Commission... 
    Training courses
    Bi-weekly pay
    Base plus commission
    Full time
    Temporary work
    Immediate start

    Sales Focus

    Chicago, IL
    22 hours ago
  • $125k

     ...Family Heritage Division has openings for a Sales professional in the Frankfort area. This...  .... This is a full time position which provides great work life balance, flexibility and...  ...500 per month) • Complete Initial basic training (1st week), ongoing training system and on... 
    Training courses
    Full time
    Local area

    Krause Agency

    Chicago, IL
    4 days ago
  • $600 per week

     ...Job Description Job Description Sales Representative – Veteran-Owned Company | Six-Figure Opportunity...  ...Earning Potential ~$600/week paid training and ramp-up pay ~ Uncapped...  ...canvassing, referrals, networking, and company-provided opportunities Conduct free exterior... 
    Training courses
    Full time

    Excel Roofing and Restoration

    Lombard, IL
    16 days ago
  •  ...Inside Sales Representative The Inside Sales Representative is responsible...  ...relationships while providing technical sales support for...  ...representative works closely with outside sales personnel, service...  ...Participate in product training provided by manufacturers and... 
    Training courses
    Work at office

    Flow Control Group

    Melrose Park, IL
    3 days ago
  •  ...Job Description Job Title: Pro AV Sales Representative (Salary-Based Position) Company:...  ...Company Description Mesa Electronics, Inc. provides advanced systems solutions to private...  ...to fulfill this position ASAP, on-site training will be provided. Company Description... 
    Training courses
    Full time
    For contractors
    Local area
    Immediate start

    Mesa Electronics, Inc.

    Lombard, IL
    15 days ago
  • $100k - $250k

     ...Job Description Job Description Position: Business Development Roofing Sales Representative High-Earning Sales Opportunity – Training Provided Responsibilities • Generate leads in the field • Canvass and Identify homes with roofing damage • Inspect roofs... 
    Training courses
    Traineeship

    Fresh Page Home Improvement

    Downers Grove, IL
    a month ago
  • $20 per hour

    Patient Care Coordinator (Luxury Aesthetic Sales Consultant) $20/hr + Uncapped Commission | Average Earnings: $90,000-$140,000+ | Full Training Provided Role Summary As a Patient Care Coordinator (PCC), you’ll be the face of the LaserAway experience — leading personalized... 
    Training courses
    Weekend work
    Afternoon shift

    LaserAway

    Chicago, IL
    1 day ago
  • $50k - $60k

     ...experience? With our award-winning training, you'll get everything you...  ...to advance into leadership, sales, or management. Job...  ...device, and the latest technology provided. We are driven by a shared...  ...pest issues both inside and outside homes or businesses, full... 
    Training courses

    Critter Control

    Broadview, IL
    22 hours ago
  •  ...Year Up United is a one-year or less, intensive job training program that provides young adults with in-classroom skill development, access to internships...  ...Career growth paths include: - Financial advisory - Sales specialist - Product Support - Sales operations and... 
    Training courses
    Internship
    Monday to Friday

    Year Up United

    Franklin Park, IL
    3 days ago
  •  ...eager to let data drive every clinical decision. You will be trained to interpret quantitative EEG (qEEG) brain maps and use that...  ...What You Will Do Interpret qEEG brain maps (full training provided), integrate neuropsychological test data, and use that data to... 
    Training courses
    Full time
    Part time
    Flexible hours

    NEUROHEALTH ASSOCIATES PC

    Oak Brook, IL
    2 days ago
  • $68k - $125k

     ...Description: Want to develop elite sales skills and join a fast-paced...  ...positive team culture? Our representatives typically earn $1,800–$2,500...  ...performers Comprehensive training from industry experts...  ..., we'll fully train you and provide the exact tools and scripts... 
    Training courses
    Weekly pay
    Contract work
    Flexible hours

    United Solar Co

    Chicago, IL
    1 day ago
  •  ...is looking to add to our service team! We have one of the best training programs in the industry, with technology-based training, FREE...  ...train to fame! Our state-of-the-art, paid training program will provide you with the tools you need to succeed. We promote from within,... 
    Training courses
    Hourly pay

    Blue Ribbon Restaurants-Novi

    North Riverside, IL
    4 days ago
  • $70k - $85k

     ...Inside Sales Representative The Inside Sales Representative (ISR) is a key member of Fortinet's sales organization...  .... Fortinet invests heavily in its people providing comprehensive onboarding, continuous technical and sales training, and ongoing enablement to ensure your long... 
    Training courses
    Worldwide
    Home office

    Edelman

    Chicago, IL
    22 hours ago
  • We’re hiring a Sales & Marketing Representative to help represent our clients through face-to-face customer...  ...Every team member receives hands-on training, ongoing coaching, and mentorship to...  ...required; comprehensive training is provided. Paid, hands-on training.... 
    Training courses

    Accure Inc

    Lombard, IL
    3 days ago
  •  ..., gain knowledge of company offerings to better serve clients, provide excellent service to customers and team members, along with work...  ...role may include competitive weekly pay, flexible scheduling, training provided, a supportive work environment, opportunities for advancement... 
    Training courses
    Weekly pay
    Flexible hours
    Shift work

    TradeJobsWorkforce

    Riverside, IL
    2 days ago
  •  ...expanding, and we are looking to hire a Outside Sales Representative in Chicago, IL and the surrounding area. This position provides the opportunity for rapid income growth...  ...growth opportunities. We offer: Field training by our top and most experienced agents... 
    Training courses
    Local area

    EMPOWER Business Group

    Chicago, IL
    1 day ago
  •  ...is looking to add to our service team! We have one of the best training programs in the industry, with technology-based training, FREE...  ...train to fame! Our state-of-the-art, paid training program will provide you with the tools you need to succeed. We promote from within,... 
    Training courses
    Hourly pay

    Blue Ribbon Restaurants-Novi

    North Riverside, IL
    4 days ago
  •  ...Rivercity Insurance and Financial Services is seeking motivated Sales and Marketing professionals to grow within the insurance...  ...Commission-based compensation Performance-based earnings Training and mentorship provided Growth opportunities in sales leadership and management... 
    Training courses

    Rivercity Insurance & Financial Services

    Chicago, IL
    4 days ago
  •  ...management). Scale: Leverage professional training and a proven system to grow your own book of business. The Opportunity: We provide a turnkey independent-contractor business...  ...Top Performers: Exceed $1M in annual sales. Unlimited Earning: Enjoy uncapped,... 
    Training courses
    For contractors
    Local area
    Immediate start

    Best Version Media

    Western Springs, IL
    a month ago
  •  ...to shifting priorities and business needs. Other duties include provide excellent service to customers and team members, respond...  ...role may include competitive weekly pay, flexible scheduling, training provided, a supportive work environment, opportunities for advancement... 
    Training courses
    Weekly pay
    Immediate start
    Flexible hours
    Shift work

    TradeJobsWorkforce

    Riverside, IL
    1 day ago
  • $50k - $150k

     ...Dynamic 365 Solution Sales Specialist Chicago, Illinois, United States SALES $ 50,000.00 - 150,000.00 (US Dollar) ITC Technologies...  ...Technical Sales & Service Support Product Selling Training Provided Dynamics 365 CRM Dynamics 365 Business Central... 
    Training courses
    Contract work
    Worldwide

    ITC Worldwide

    Chicago, IL
    22 hours ago
  •  ...multiple customer service positions to our growing team of remote representatives. This is a full time position with upwards mobility and the...  ...the support of management Benefits Include: ~ Full training provided ~100% Virtual Work from Home ~ Career growth and... 
    Training courses
    Weekly pay
    Full time
    Local area
    Remote work
    Work from home

    Zuzick & Associates

    Chicago, IL
    22 hours ago
  • $17 per hour

     ...at major retail stores within an assigned territory to represent our clients’ brands by setting up and maintaining a...  ...Store-to-store drive time and mileage assistance Training: Paid training time is provided to prepare you for program success Time Off: Accrue... 
    Training courses
    Bi-weekly pay
    Hourly pay
    Part time
    Work from home
    Monday to Friday
    Afternoon shift

    ActionLink

    Riverside, IL
    28 days ago
  •  ...assist with organizing, stocking, and general upkeep, along with provide excellent service to customers and team members, respond...  ...role may include competitive weekly pay, flexible scheduling, training provided, a supportive work environment, opportunities for advancement... 
    Training courses
    Weekly pay
    Flexible hours
    Shift work

    TradeJobsWorkforce

    Riverside, IL
    4 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Outside Sales Representative (Training Provided). Be the first to apply!