Becoming an Associate with 1099 Workers
What You Need to Know

No. Whether you are self employed, freelancer, small business owner, or part-time or full time employee of another company, you can enroll as an Associate with 1099 Workers. 

Most individuals can enroll if they are: 

• 18 years of age or older 
• Legally authorized to work in the U.S. 
• Actively working 

To access group benefits, you must be employed by the sponsoring organization.

By enrolling, you become a part-time, on-call W-2 Associate of 1099 Workers. This structure allows you to access benefits typically only available through employers.

As an Associate, your role is flexible and on-call. You may choose to participate in promoting or engaging with the 1099 Workers platform, but there are no required tasks, minimum hours, or obligations tied to your enrollment.

No. The Associate role is part-time, flexible, and on-call.

There are no required hours, tasks, or job responsibilities tied to your enrollment.

No. Your role is structured as part-time and flexible, and you are not required to perform any specific tasks or meet minimum hour requirements. Any services you choose to perform are voluntary and subject to mutual agreement.

No. This does not affect your current employment, self-employment, or business. You can continue working wherever and however you choose.

The easiest way to think about it is like a very small part-time role — not for income, but to access group benefits.

No. You are enrolling through 1099 Workers to access group health benefits.

Your medical coverage is provided through 1099 Workers who sponsors the group plans. 1099 Workers works with TPAs and claims administrators who administer the health plans.

1099 Workers has year-round enrollment that is open month-to-month. 

How soon can I start my benefits?

Your earliest available start date depends on when you complete your enrollment:

• Enroll before the 14th of the month → you can start benefits as early as the 1st of the next month
• Enroll on or after the 14th → your earliest start date is the 1st of the month after that

Important: No matter which start date you choose, you must fully complete your enrollment and onboarding (including I-9 and E-Verify) by the 14th of the month before your selected start date. If that deadline is missed, your start date automatically moves to the 1st of the following month.

Example: Enroll on August 10th → you can select September 1st as your start date, as long as you complete all onboarding by August 14th. If onboarding isn’t finished until after the 14th, your start date shifts to October 1st.

Payments: Your first full month’s payment is collected on the 15th of the month before your benefits start (e.g., August 15th for a September 1st start). Regular payments then continue on the 1st and 15th going forward.

Enrollment Sequence

1. Complete online enrollment and onboarding
2. Pay for benefits
3. Benefits begin on your selected start date

1. Complete your profile, 
2. Select your benefits, 
3. Digitally sign your new hire packet,  
4. Submit your enrollment application, 
5. Complete your I-9, E-Verify, and Direct Deposit verification, 

Once completed, you will receive a Welcome email and you can access all your plan information and resources inside your 1099 Workers Community portal.

Each benefit option during enrollment has a View Details link that opens the full plan brochure — including things like the prescription formulary and provider network links. We’d recommend reviewing this before selecting, especially if you take specific medications or see specific providers regularly.

Form I-9 is a requirement for all U.S. employers. It is used to verify the identity and employment authorization of individuals hired for work in the United States.

You are enrolling through 1099 Workers, which provides access to group benefits and manages your enrollment and ongoing support.

Through our platform, you have access to:

• Major Medical plans on the Cigna network
• Major Medical plans on our Open Access network
• Minimum Value (MV) Plans on our Open Access network – a lower-cost alternative

Your available plan options will be shown during enrollment. Claims for all plans are administered by Imagine360.

No. You are not enrolling directly with an insurance carrier.

1099 Workers is the sponsor to the group benefits and our platform helps manage your enrollment experience.

You will have the option to pick from one of our several medical plan options, including low deductible, high deductible, and HSA options. 

From there, you have additional benefit options that you can take or leave, such as dental, vision, accident, and other supplemental plans. 

You must enroll in one of the medical benefits in order to enroll in any of the supplemental group benefits or contribute to 401k. 

Yes.

You may make changes to your benefit selections up until the 15th of the month prior to your selected benefit start date.

After that date changes are only allowed if you experience a qualifying life event (QLE) or during annual open enrollment.

Please note: If you are enrolled in a CoreChoice health plan, qualifying life events only allow you to add or remove eligible dependents. Changes to your medical plan selection are only allowed during annual open enrollment.

Open enrollment typically occurs towards the end of 4th quarter of the year (beginning around November). 

During this time, you will be notified of: 

• Any plan design changes 
• Any premium (rate) adjustments 
• Your opportunity to select a new plan or keep your current one 

Our group health plans renews on a calendar year basis, January to December. This means any changes to plan offerings or pricing take effect at the start of the new plan year in January. 

All major medical deductibles and maximum out-of-pocket (OOP) limits operate on a calendar year basis. 

This means they reset every year on January 1. 

No. Deductibles and out-of-pocket amounts do not transfer from plans you had with other employers, individual marketplace plans, or other insurance providers.

When you enroll in a new plan through 1099 Workers, your deductible and out-of-pocket totals will begin fresh based on the plan you select.

Deductibles for medical plans also reset each year on January 1.

The provider network depends on the plan you select.

Major Medical – Cigna Network

Uses the Cigna PPO network. Click Here

To search for providers:

• Enter your search criteria
• Select “Continue as Guest”
• Select “PPO, Choice Fund PPO”

Major Medical – Open Access Network

Gives you open access to any licensed provider nationwide – there’s no narrow network to stay inside of. For the simplest, fastest billing, use a provider on the Multiplan Practitioner & Ancillary network. Click Here

• Select “Multiplan Practitioner & Ancillary”

See the “Open Access Plan” section below

Minimum Value – Open Access Network

Same open access design, with annual service limits on certain services. See the “Minimum Value (MV) Plans” section below.

Yes, through Veracity Rx. Coverage includes ACA preventive generics, generic, preferred brand, and non-preferred brand medications. Specialty medications are not covered on any plan.

A digital ID card becomes available in your Portal once your first payment is collected. A physical card is mailed out roughly two weeks after your second payment, typically arriving around your benefit start date.

I can’t find my ID card — who do I contact?

Start by logging into your Portal — your digital ID card is always available there. If you still can’t locate it, reach out to our support team.

If you experience a qualifying event and want to adjust benefits, you can call our support team within 30 days of the event. 

Here are some examples of qualifying events and the necessary documentation: 

• Becoming a parent: Birth certificate or adoption record 
• Getting married: Marriage certificate 
• Getting a divorce: Filed court papers 

For a complete list of qualifying life events, click Here. 

Once you or one of your covered dependents becomes eligible for Medicare, you have the option to stay on your current medical plan or change to Medicare.

If you have questions about how Medicare eligibility may affect your benefits, please contact support for assistance.

Yes. You may submit your cancellation request of benefits at any time through your 1099 Workers Community portal.

Because your benefits are provided through your role as a 1099 Workers Associate, cancelling your benefits will also result in resignation from your Associate position.

Cancellation requests are generally subject to a minimum 30-day notice period. As a result, requests received after the 15th of a month are typically not eligible for an effective termination date on the upcoming 1st of the following month. For example, a request received on May 16 would generally have an earliest effective termination date of July 1.

Please refer to the Terms & Conditions for complete cancellation and re-enrollment provisions.

These plans use our Open Access Network. Unlike a traditional plan, you’re not limited to a narrow list of providers – you can see any licensed doctor or facility in the country.

Seeing a licensed provider on the Multiplan Practitioner & Ancillary network gives you the simplest, fastest billing, but it’s not required. You can search for providers on this network Here

• Select “Multiplan Practitioner & Ancillary”

You don’t need to check – any licensed provider is available to you. If your doctor happens to participate in the Multiplan Practitioner & Ancillary network, billing will typically be a little simpler. You can call the Member Experience Team for help finding one in the Multiplan Practitioner & Ancillary network.

Yes — any licensed doctor, regardless of network participation.

There’s no traditional “out-of-network” restriction – every licensed provider is accessible. Instead of a negotiated network discount, hospital and facility care is paid at a set benchmark rate directly to the facility. Most facilites accept this rate without any extra steps from you. If one doesn’t, our Member Experience Team works it out directly with the facility on your behalf.

No. Major Medical Open Access plans do not have annual visit or service limits.

The Out-of-Pocket Maximum is the most you would pay in a plan year for covered medical services through deductibles, copays, and coinsurance. After reaching this amount, the plan pays 100% of additional covered costs for the calendar year.

Referrals are generally not required for specialist care.

However, some services do require pre-notification or pre-authorization, such as:

• Hospital admissions
• Outpatient surgery
• Certain inpatient services
• Some advanced procedures

If pre-notification is not completed when required, a penalty may apply.

Emergency room services are covered, even if the provider is out-of-network.

Federal law also protects you from surprise billing for emergency services and certain hospital-based services.

Advanced imaging and diagnostic testing (MRI, CT, PET scans, and similar) must be done at a freestanding facility – one that isn’t owned by or connected to a hospital – to be covered. The same test at a hospital-owned facility costs significantly more and isn’t covered the same way.

That’s normal and doesn’t mean they won’t accept it. Have the front desk call the number on your ID card – even while you’re there – and we’ll confirm your benefits and talk to the provider directly if needed.

Call the number on your ID card right away, or contact Upland Advocacy (support@uplandadvocacy.com, 833-9-UPLAND). They’ll work directly with the provider or collections agency on your behalf, at no cost to you.

Yes, through Veracity Rx. This plan covers ACA preventive generic and generic, preferred brand and non-preferred brand medications. Specialty medications are not covered on any plan.

This plan gives you open access to any provider in the country, with no annual visit limits, backed by a team that resolves billing issues directly on your behalf. For hospital and facility care specifically, your plan pays a set, fair rate rather than negotiating a network discount – almost all facilities accept this, and if one doesn’t, we handle it for you.

These plans use our Open Access Network. You can see any licensed provider in the country.

Seeing a licensed provider on the Multiplan Practitioner & Ancillary network gives you the simplest, fastest billing. You can search for providers on this network Here

• Select “Multiplan Practitioner & Ancillary”

You don’t need to – any licensed provider is available to you. You can call the Member Experience Team for help finding one in the Multiplan Practitioner & Ancillary network for the simplest billing.

Yes — any licensed doctor, regardless of network participation.

There’s no traditional “out-of-network” restriction – every licensed provider is accessible. Hospital and facility care is paid at a set benchmark rate rather than a negotiated discount; almost all facilities accept it, and our Member Experience Team steps in directly if one doesn’t.

A copay is a fixed dollar amount you pay for a covered service.

Examples may include:

• Primary Care Visit
• Specialist Visit
• Urgent Care
• Emergency Room
• Imaging or Lab Services

After your copay, the plan may pay the remaining covered amount based on your plan benefits and annual service limits.

Yes, on some services. Primary care, specialist, lab work/X-ray and urgent care visits are unlimited. Annual limits apply to such services including:

• Emergency room visits
• Emergency transportation
• Inpatient hospital days
• Inpatient/Outpatient surgeries
• Mental health outpatient visits
• Rehabilitation services

Once the yearly limit is reached, additional services in that category are not covered. Always check your specific plan brochure for full details.

The Out-of-Pocket Maximum is the most you would pay in a plan year for covered medical services through deductibles, copays, and coinsurance. After reaching this amount, the plan pays 100% of additional covered costs.

For Minimum Value plans, it’s important to understand:

Coverage is based on a set number of services per year (such as hospital stays, surgeries, etc.), each with a fixed copay. As long as you stay within those service limits, you only pay the listed copay amounts.

Once you exceed those annual service limits, any additional services are not covered, and you are responsible for the full cost — even if you have already reached the Out-of-Pocket Maximum.

In practice, most members will experience these plans as copay-based coverage within defined service limits, rather than reaching the Out-of-Pocket Maximum.

Referrals are generally not required for specialist care.

However, some services do require pre-notification or pre-authorization, such as:

• Hospital admissions
• Outpatient surgery
• Certain inpatient services
• Some advanced procedures

If pre-notification is not completed when required, a penalty may apply.

Emergency room services are covered, even if the provider is out-of-network.

Federal law also protects you from surprise billing for emergency services and certain hospital-based services.

Advanced imaging and diagnostic testing (MRI, CT, PET scans, and similar) must be done at a freestanding facility – one that isn’t owned by or connected to a hospital – to be covered. The same test at a hospital-owned facility costs significantly more and isn’t covered the same way.

Simply provide your insurance ID card.

Your provider should use the billing instructions listed on the card when submitting claims. If a provider says they don’t recognize your plan, have them call the number on the card.

Call the number on your ID card right away, or contact Upland Advocacy (support@uplandadvocacy.com, 833-9-UPLAND). They’ll work directly with the provider on your behalf, at no cost to you.

Yes, through Veracity Rx. This plan covers ACA preventive generic and generic medications only. Preferred brand, non-preferred brand and specialty medications are not covered.

This plan gives you open access to any provider in the country at a low monthly cost, with unlimited primary care, specialist, lab and urgent care visits. In exchange, a defined set of services carry annual limits, and a small number of services – including hospice, dialysis, chemotherapy, DME, and skilled nursing – aren’t covered at all. Review the full list above before you enroll, especially if you or a dependent has ongoing or complex conditions.

When selecting benefits during enrollment, the pricing shown reflects your semi-monthly payment before taxes and fees.

After you select all desired benefits and move to the summary page, your full payment breakdown will be displayed, including:

• Monthly payment for each selected benefit
• Benefit subtotal
• Applicable taxes and fees
• Total monthly payment
• Total semi-monthly payment

Your Total Semi-Monthly Payment is the amount that will be processed from your account on the 1st and 15th of each month.

Applicable taxes and fees help cover the costs required to provide and maintain your benefits program. This includes:

• Applicable payroll taxes
• Benefit administration costs
• Payroll processing fees
• Software and platform fees
• Other required operational fees related to maintaining the benefits program

These charges are added to your selected benefit premiums and are included in your total payment amount.

1099 Workers processes payments on the 1st and 15th of each month.  

Payments are collected prior to your benefits becoming active. 

For example, if your benefits start on January 1, your first payments will be collected on December 1 and December 15. 

1099 Workers will collect the payments from your chosen payment method (set up during the online enrollment process) and process that through our payroll. 

Because you are enrolled as a W-2 Associate, all benefit payments are processed through payroll.

You fund 100% of your selected benefits, including applicable taxes and fees. This results in a minimal net paycheck, which is why you may see a small salary amount.

When you enroll with 1099 Workers, you are onboarded and hired as a part-time W-2 employee of 1099 Workers. Payments you make are processed through our payroll to cover the cost of insurance, applicable taxes and fees, and typically result in a negligible net salary. 

You receive a W-2 at the end of the year showing wages and pre-tax benefit contributions. This does not change your primary status as a 1099 contractor, self-employed individual, or business owner. 

Possibly. Because every business and tax situation is different, we strongly recommend consulting your own CPA or tax advisor for confirmation. We do not provide tax advice.  

Many individuals who enroll with 1099 Workers are self-employed, freelancers, or business owners, and in many cases the cost of health insurance may still be deductible as a business expense.