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Residual Income Jobs in Chicago, IL (NOW HIRING)

SharpPencil AI

Be Seen First

Sales Representative

Chicago, IL · Remote

$200K/yr

Residual Income: Build a book of business! You earn commission every month the client pays their bill, creating cumulative income that grows over time. * Total Account Commission: You get paid on any ...

Celero Commerce

Account Executive, Payments

Rosemont, IL · On-site

$90K - $110K/yr

Flexibility to help transition existing residual income - flexible structures to help bridge legacy income * Competitive base with uncapped commission and residual earning potential * A strong ...

Celero Commerce

Account Executive, Payments

Rosemont, IL · On-site

$90K - $110K/yr

Flexibility to help transition existing residual income - flexible structures to help bridge legacy income * Competitive base with uncapped commission and residual earning potential * A strong ...

AO Globe Life

Remote Sales Specialist

Waukegan, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Waukegan, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Waukegan, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Waukegan, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

AO Globe Life

Remote Sales Specialist

Aurora, IL · On-site +1

Plus, enjoy lifelong residual income through renewals! * 🔋 Bonuses & Benefits: Earn weekly pay with exciting bonuses that reward your outstanding performance. Enjoy a unionized position with stock ...

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All JobsResidual Income JobsResidual Income Jobs in Chicago, IL

Residual Income information

See Chicago, IL salary details

$38.6K

$81.5K

$103.5K

How much do residual income jobs pay per year?

As of Aug 23, 2026, the average yearly pay for residual income in Chicago, IL is $81,470.00, according to ZipRecruiter salary data. Most workers in this role earn between $67,000.00 and $95,800.00 per year, depending on experience, location, and employer.

What is residual income?

Residual income refers to money that continues to be earned after the initial effort has been completed. This type of income often comes from investments, rental properties, royalties, or businesses that generate ongoing revenue with minimal daily involvement. It's a popular concept for those seeking financial independence because it allows for continuous earnings without constant active work. Examples include book royalties, dividends from stocks, or rental income from real estate properties.

What are the key skills and qualifications needed to thrive as a residual income specialist, and why are they important?

To thrive as a Residual Income Specialist, you need a solid understanding of financial principles, passive income strategies, and business development, often supported by experience in finance or marketing. Familiarity with CRM software, financial analytics tools, and investment platforms is typically required. Strong networking, communication, and self-motivation skills set top performers apart in this field. These abilities are essential for building sustainable income streams, managing client relationships, and adapting to changing market opportunities.

What are common challenges faced by professionals working in roles focused on building residual income?

Professionals working to build residual income often face the challenge of developing reliable revenue streams that require significant upfront effort or investment. It can take time to establish systems or products (such as rental properties, digital content, or network marketing channels) that generate ongoing income with minimal day-to-day involvement. Additionally, maintaining and scaling these income streams often requires strong self-motivation, adaptability to market changes, and effective time management. Collaborating with others, such as financial advisors or business partners, can also be essential for long-term success.

What is the difference between Residual Income vs Real Estate Agent?

AspectResidual IncomeReal Estate Agent
Required CredentialsVaries; often no formal credentials needed, but certifications can helpReal estate license required
Work EnvironmentCan be passive, from investments or royaltiesActive, client-facing sales environment
Industry UsageFinance, investments, royaltiesReal estate industry
Income TypeRecurring, passive income streamsCommission-based, active income

Residual income involves earning passive income through investments or royalties, while a real estate agent earns active commissions from property sales. Both roles are prominent in their industries, but residual income typically requires less active work once established, whereas real estate agents actively engage with clients to generate income.

What are popular job titles related to Residual Income jobs in Chicago, IL?

For Residual Income jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Residual Income jobs in Chicago, IL look for?

The top searched job categories for Residual Income jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Residual Income jobs?

Cities near Chicago, IL with the most Residual Income job openings:

Residual Income jobs near you
Infographic showing various Residual Income job openings in Chicago, IL as of August 2026, with employment types broken down into 67% Part Time, and 33% Contract. Highlights an 67% In-person, and 33% Remote job distribution, with an average salary of $81,470 per year, or $39.2 per hour.

Sales Representative

SharpPencil AI

Chicago, IL • Remote

$200K/yr

Full-time

Re-posted 17 days ago

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After you apply to this job, you can share why you’re interested to jump to the top of the candidate list.

Job description

About the Role: Sharp Pencil is a rapidly growing startup revolutionizing the financial services industry. We utilize advanced AI technology to provide third-party bookkeeping, accounting, tax preparation, and business consulting services to small and medium-sized businesses.

We are seeking entrepreneurial-minded Sales Representatives to join our team nationwide. This is a purely Commission-Driven, 1099 Independent Contractor position that offers high earning potential through a lucrative residual income model. You will have the freedom to work from home, set your own schedule, and sell without territory restrictions.

Why Join Us?

  • High Commission Rate: Earn a flat 20% commission on all billing.
  • Residual Income: Build a book of business! You earn commission every month the client pays their bill, creating cumulative income that grows over time.
  • Total Account Commission: You get paid on any service the client adds (payroll, merchant services, etc.), even if they add it later without your direct involvement.
  • Growth Potential: As a new company, we offer the unique opportunity to grow your career alongside the business.
  • Flexibility: 100% remote, home-based, with no protected territories—sell to business owners anywhere in the U.S.

Responsibilities:

  • Prospect and contact small to medium-sized businesses to introduce Sharp Pencil’s AI-driven bookkeeping and financial solutions.
  • Present and sell company services to new and existing customers, effectively communicating the value of outsourcing financial tasks.
  • Reach agreed-upon sales targets to maximize personal revenue.
  • Manage the sales cycle from initial contact to closing the deal.
  • Resolve customer inquiries and offer solutions to drive revenue.
  • Set follow-up appointments to keep customers aware of the latest developments and service add-ons.

Qualifications:

  • Self-Starter: Must be disciplined and motivated to work independently in a remote environment.
  • Previous experience in sales, business development, or customer service (B2B sales experience is a plus).
  • Ability to build rapport with clients and maintain long-term professional relationships.
  • Strong negotiation skills and a "hunter" mentality.
  • Familiarity with CRM platforms and comfortable using technology.
  • Deadline and detail-oriented.

Compensation:

  • Type: 1099 Independent Contractor.
  • Pay Structure: 100% Commission-Only.
  • Earning Potential: Uncapped.
    • Note on Earnings: Income is cumulative. While first-year earnings may vary as you build your pipeline (e.g., $60k–$120k), the residual model allows for significant jumps in subsequent years (e.g., $200k+) as your client base renews and expands.