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Remote 1099 Insurance Agent Jobs in Silver Spring, MD

HMG Careers

Remote Life Insurance Agent

Washington, DC · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Life Insurance Agent

Baltimore, MD · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Life Insurance Agent

Alexandria, VA · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Kimbrell Agency

Life Insurance Agent

Washington, DC · Remote

$50K - $100K/yr

Kimbrell Agency Remote Employment Type: Contractor Compensation $50,000 to $100,000 per year (plus ... The Problem with Most Insurance Jobs: Let's be real--most agencies are desperate to hire anyone ...

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All Jobs1099 Insurance Agent JobsRemote 1099 Insurance Agent JobsRemote 1099 Insurance Agent Jobs in Silver Spring, MD

Remote 1099 Insurance Agent information

See Silver Spring, MD salary details

$25.8K

$67.2K

$125.6K

How much do remote 1099 insurance agent jobs pay per year?

As of Aug 7, 2026, the average yearly pay for remote 1099 insurance agent in Silver Spring, MD is $67,218.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,000.00 and $79,600.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote 1099 insurance agent?

To thrive as a Remote 1099 Insurance Agent, you need strong sales acumen, comprehensive knowledge of insurance products, and a valid state insurance license. Familiarity with CRM software, quoting systems, and digital communication tools is typically required. Excellent self-motivation, communication, and customer relationship skills help agents stand out in a remote, commission-driven environment. These abilities are crucial for effectively building a client base, meeting sales targets, and succeeding independently in a competitive market.

What is a Remote 1099 Insurance Agent?

A Remote 1099 Insurance Agent is an independent contractor who sells insurance policies from a remote location, rather than working onsite at an agency or company office. The '1099' refers to the IRS tax form used for independent contractors, meaning they are not employees but self-employed individuals responsible for their own taxes. These agents typically earn commissions on the policies they sell and have flexibility in setting their own schedules. They often work with multiple insurance companies and must handle their own marketing, client acquisition, and administrative tasks.

What is the difference between Remote 1099 Insurance Agent vs Remote 1099 Insurance Broker?

AspectRemote 1099 Insurance AgentRemote 1099 Insurance Broker
CredentialsLicenses required for specific insurance typesSame as Insurance Agent, plus ability to represent multiple carriers
Work EnvironmentIndependent, remote salesIndependent, remote sales with broader carrier access
Employer/Industry UsageOften contracted directly with insurance companies or agenciesTypically contracted with multiple carriers or as an independent broker
Search/Comparison IntentFocus on individual insurance sales rolesFocus on roles involving multiple carrier representation

While both roles operate remotely as 1099 independent contractors, a Remote 1099 Insurance Agent primarily sells policies for specific insurance companies, requiring relevant licenses. A Remote 1099 Insurance Broker, on the other hand, can represent multiple carriers, offering clients broader options. The key difference lies in carrier access and licensing scope, impacting the sales approach and client offerings.

What are some common challenges faced by remote 1099 insurance agents, and how can they be addressed?

Remote 1099 Insurance Agents often face challenges such as managing their own schedule, generating leads independently, and staying motivated without direct supervision. Building a strong daily routine, leveraging digital marketing strategies, and actively participating in virtual networking or training sessions can help overcome these hurdles. Additionally, effective communication with clients and insurance carriers is crucial, so utilizing reliable technology and CRM tools is highly recommended. Proactively seeking mentorship or support from online agent communities can also provide valuable guidance and encouragement.
What are the most commonly searched types of 1099 Insurance Agent jobs in Silver Spring, MD? The most popular types of 1099 Insurance Agent jobs in Silver Spring, MD are:
What are popular job titles related to Remote 1099 Insurance Agent jobs in Silver Spring, MD? For Remote 1099 Insurance Agent jobs in Silver Spring, MD, the most frequently searched job titles are:
What job categories do people searching Remote 1099 Insurance Agent jobs in Silver Spring, MD look for? The top searched job categories for Remote 1099 Insurance Agent jobs in Silver Spring, MD are:
What cities near Silver Spring, MD are hiring for Remote 1099 Insurance Agent jobs? Cities near Silver Spring, MD with the most Remote 1099 Insurance Agent job openings:
Remote 1099 Insurance Agent jobs near you

Remote Insurance Sales Agent - TV Leads Provided No Cold Calling

Taylored Legacy

Baltimore, MD • Remote

$75K - $999K/yr

Full-time

Re-posted 3 days ago

Job description

Are you a driven entrepreneur looking for a high-income career change, or an experienced insurance agent seeking better contracts and exclusive lead flow?

Most sales jobs require you to cold call strangers, chase people who never respond, or pay thousands upfront just to get started. Taylored Legacy operates differently. We provide the systems, the support, and the exclusive leads so you can focus entirely on presenting solutions and closing business.

This is a remote, commission-based opportunity with flexible scheduling and a proven nationwide platform.

We are actively expanding across Final Expense, Mortgage Protection, Annuities, and Medicare, and we are looking for driven individuals and experienced agency owners to grow with us.

Why Agents and Agency Owners Choose Taylored Legacy

✅ Top-Tier Contracts: Earn up to 145% contracts based on production and agency building.
✅ True Ownership: Non-captive platform with day-one vesting and full book ownership.
✅ Exclusive Lead Flow: High-intent leads, including real-time inbound TV leads, converting as high as 40% for top closers.
✅ Free Lead Options: Available to help you get started immediately.
✅ Comprehensive Portfolio: Top carriers across Final Expense, Mortgage Protection, Annuities, and Medicare coming soon.
✅ Ultimate Flexibility: 100% remote work from anywhere in the United States.

Direct Mentorship & Proven Systems

You aren't just getting a contract; you are getting a blueprint. You will receive direct mentorship from our founder, who has personally produced over $39 million in the field using the exact same systems you will be using.

✅ Proven Track Record: Our agency has paid out over $200 million in commissions to our agents nationwide.
✅ Built-in CRM: Automated dialing platform with real-time AI feedback and a management platform at no cost to you.
✅ Step-by-Step Training: For both brand-new agents and experienced producers.
✅ Transparency: Want to see how we train before you apply? Check out our founder's free training content on:

Instagram /officialadamhale

TikTok /finalexpensetrainer

YouTube at /adamhale

Who This Is For

✅ Entrepreneurs: Individuals seeking a performance-based income with no ceiling.
✅ Licensed Agents: Looking for higher contracts and better lead access.
✅ Agency Owners: Seeking a non-captive home with top-tier support and carrier access.

Not Licensed Yet?

No problem. We offer a discounted, guided licensing path for hard-working entrepreneurs ready to start their new career. Many of our top earners started with zero insurance experience and built six-figure incomes within their first year.

Quick Apply

Takes under 2 minutes. No commitment required to learn more about the opportunity.

This is a 1099 independent contractor opportunity. Income is performance-based and varies by individual activity and production. Taylored Legacy is an equal opportunity organization.

Company Description

Taylored Legacy is a family-owned national insurance organization built to help agents and agency owners succeed while protecting families across the United States. Specializing in Final Expense, Mortgage Protection, Annuities, and Medicare, our team has helped protect hundreds of thousands of families and has paid over $200 million in commissions to the agents and entrepreneurs who represent us.

We are one of the fastest-growing independent marketing organizations in the insurance industry, powered by a proven system that combines exclusive inbound leads, daily compensation, contracts up to 145%, and true long-term book ownership on a fully non-captive platform.

Agents and agency owners choose Taylored Legacy because we deliver what others only promise. Our in-house lead generation includes high-intent TV, digital, and direct mail campaigns. Our compensation is transparent with daily payouts. Our training and mentorship programs are hands-on and ongoing. And our remote-first model gives producers the flexibility to build their business from anywhere.

We are committed to building careers and agencies, not just writing contracts. Whether you are a brand-new entrepreneur or a seasoned agency owner looking for a better home, Taylored Legacy provides the carriers, leads, technology, and support to help you reach your full potential.

Commission-based 1099 independent contractor opportunity. Income varies by individual performance and production level.