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Remote Direct Entry Pilot Jobs in Chicago, IL (NOW HIRING)

Culligan NA

Be Seen First

Senior Sales Engineer - Industrial

Chicago, IL · Remote

$100K - $150K/yr

Director of Global Accounts Location: Hybrid from Rosemont, Libertyville or Downtown Chicago, IL ... fully Remote with travel We offer competitive compensation including base $100-150k plus ...

New

Culligan NA

Be Seen First

Senior Sales Engineer - Industrial

Chicago, IL · Remote

$100K - $150K/yr

Director of Global Accounts Location: Hybrid from Rosemont, Libertyville or Downtown Chicago, IL ... fully Remote with travel We offer competitive compensation including base $100-150k plus ...

New

Culligan NA

Be Seen First

Senior Sales Engineer - Industrial

Chicago, IL · Remote

$100K - $150K/yr

Director of Global Accounts Location: Hybrid from Rosemont, Libertyville or Downtown Chicago, IL ... fully Remote with travel We offer competitive compensation including base $100-150k plus ...

New

Medela

Manager, Medical Affairs Operations

Chicago, IL · On-site +1

$130K/yr

Manage the operational execution of global Medical Affairs programs, pilot initiatives, feasibility ... Minimum 2 years of direct people leadership experience * Proven ability to manage complex cross ...

Zero Hash

VP/SVP, Head of Business Operations

Chicago, IL · On-site +1

... pilots to change management and adoption. * Identify high-value use cases across teams (support ... Build the analytical backbone for strategic decisions - pricing, market entry, and build-vs-partner ...

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Showing results 21-40

All JobsDirect Entry Pilot JobsRemote Direct Entry Pilot JobsRemote Direct Entry Pilot Jobs in Chicago, IL

Remote Direct Entry Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do remote direct entry pilot jobs pay per year?

As of Aug 16, 2026, the average yearly pay for remote direct entry pilot in Chicago, IL is $134,863.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,000.00 and $159,700.00 per year, depending on experience, location, and employer.

What are the most commonly searched types of Direct Entry Pilot jobs in Chicago, IL?

The most popular types of Direct Entry Pilot jobs in Chicago, IL are:

Remote Direct Entry Pilot jobs near you

Licensed Insurance Sales Professional

Green Brook Insurance

Wheaton, IL • Remote

$65K - $85K/yr

Full-time

Medical, Life

Posted 7 days ago

Job description

At Green Brook Insurance, we believe every person deserves Knowledge, Options, and Care when protecting what matters most. We are seeking licensed, relationship-focused insurance professionals to help prospective clients understand their choices and confidently select coverage.


This opportunity focused on conversations, guidance, follow-up, and closing—not data entry or administrative work. Green Brook’s support team handles quote entry, proposal preparation, requested updates, and payment processing.


Professionals may work with life, home, auto, and business insurance opportunities. There are no required hours or set schedule. Compensation is commission-only: the sales professional receives 50% of the agency commission Green Brook receives on policies they help place.

Responsibilities
  • Respond promptly and professionally to the leads and opportunities you accept.
  • Listen carefully to understand why the prospect is shopping, what concerns them, and what they want to protect.
  • Conduct helpful, relationship-focused insurance conversations.
  • Gather necessary information through conversation and clearly guide the Proposal Team.
  • Explain coverage options in simple language and provide appropriate licensed guidance.
  • Answer questions, address concerns, recommend next steps, and ask for the business.
  • Maintain ownership of follow-up until the prospect makes a decision.
  • Direct the Proposal Team regarding quote changes or proposal updates without completing data entry.
  • Transfer ready clients to the Payment Processing Specialist.
  • Maintain all required insurance licenses and follow privacy, recording, and insurance compliance requirements.
  • Protect client information and represent Green Brook with expertise, care, integrity, and professionalism.


Requirements
  • Hold an active Property Casualty and/or Life Health insurance license in good standing.
  • Be eligible for any carrier appointments needed for the insurance products you sell.
  • Communicate clearly, patiently, and with care.
  • Listen closely, uncover the prospect’s true concern, and recommend suitable coverage.
  • Explain insurance options in simple language and confidently ask for the business.
  • Follow up promptly and take ownership of every opportunity you accept.
  • Work independently while cooperating well with Green Brook’s support team.
  • Protect client information and follow all insurance, privacy, recording, carrier, and agency requirements.
  • Have reliable internet, a suitable computer, and a private remote workspace.
  • Be comfortable with a non-exclusive, commission-only 1099 relationship with no guaranteed income or lead volume.


Experience selling life, home, auto, or business insurance is preferred. Partners do not need experience in every product line and will only advise clients on products they are properly licensed to sell.

Benefits
Work from Home###Flexible Schedule###Mon-Fri Schedule###Robust Training###50% Commisions Green Brook Receives###No Data Entry###Dedicated Support for Quotes, Change Requests, etc.###Errors and Omissions Coverage Provided###