Check’s Workers’ Compensation Insurance Go-to-Market Playbook

Explore strategies for successfully selling workers' compensation insurance and enhancing payroll offerings.

Introduction

Workers’ compensation insurance is a form of insurance providing wage replacement and medical benefits to employees injured in the course of employment. Payroll and workers comp are deeply intertwined: most states require workers comp insurance as soon as an employer hires their first employee, and insurance premiums are calculated at least in part using payroll amounts. As such, legacy payroll providers have been incorporating workers comp into their product suite for over 30 years, and it is an established product offering your payroll sales representatives can easily bring up during the payroll sales conversation.

This playbook provides Check’s prescriptive guidance for selling workers comp insurance. We will cover several key Go-To-Market (”GTM”) areas, including:

  1. A brief overview of the workers comp landscape, including key stakeholders and customer types you will encounter
  1. Best practices on how to generate interest in your workers comp offering
  1. An outline of how you should sell workers comp in relation to your payroll sales motion and specific sales tactics to help your reps successfully take workers comp prospects from interest to live

Overview of the Workers Comp Landscape

Background on Workers Comp

Workers comp insurance is a type of insurance policy that provides benefits to employees who are injured or become ill as a result of their job. This insurance policy is designed to protect both the employer and the employee by providing financial assistance to cover medical expenses, lost wages, and other related costs.

Workers comp insurance is typically required by law in most states as soon as an employer hires their first employee. The regulatory-required coverage provided by a workers comp policy varies depending on the state, but typically includes benefits for medical expenses, disability payments, and rehabilitation costs.

When an employee is injured on the job, they can file a claim with their employer's insurance company to receive compensation for their medical expenses and lost wages. In exchange for receiving benefits under workers comp insurance, employees generally waive their right to sue their employer for negligence or other claims related to the injury or illness.

Workers comp premiums are calculated using a number of inputs, but one of the main ones is payroll expense. There are two main types of plans: pay-as-you-go (PAYGo) workers comp insurance and yearly audit workers comp insurance. Pay-as-you-go workers comp insurance allows businesses to make premium payments in real-time based on their actual payroll amounts, while yearly audit workers comp insurance requires businesses to estimate their payroll amounts at the beginning of the policy term and make a lump-sum payment for their workers comp insurance premiums, adjusting at the end of the year as necessary.

Understanding the key stakeholders

In considering offering workers comp insurance as part of your payroll line of business, it is critical to understand the various stakeholders involved with the workers comp industry and individual claims. Comprehending the stakeholders involved in workers comp enables your team to make informed decisions, offer appropriate coverage, build strong relationships, and create a safer and more secure work environment for their employees.

  • Employer: The employer is responsible for purchasing workers comp insurance to provide benefits to their employees in the event of a work-related injury or illness. Employers must comply with state laws and regulations related to workers comp insurance and must pay premiums to their insurance carrier to maintain coverage.
  • Employee: The employee is the beneficiary of workers comp insurance coverage and is entitled to benefits if they are injured or become ill as a result of their work. Employees must report workplace injuries or illnesses to their employer and seek medical treatment as needed.
  • Insurance Broker: In 46 states (excluding ND, OH, WA, WY), an employer is able to partner with an insurance broker to purchase workers comp insurance; however they are not legally required to can instead purchase directly from the carrier. Brokers offer advice to business owners, and once a policy is chosen they help negotiate the terms of coverage with the insurer. Note that in the 4 excluded states, employers must buy worker comp policies directly from the state.
  • Insurance Carrier: The insurance carrier is responsible for underwriting workers comp insurance policies and providing coverage to businesses. Insurance carriers must comply with state laws and regulations related to workers comp insurance and must pay benefits to injured or ill employees as required by law.
  • Other notable stakeholders:
    • Medical Providers: Medical providers, including doctors, hospitals, and clinics, play a critical role in workers comp insurance by providing medical treatment to injured or ill employees. Medical providers must be authorized by the insurance carrier and must comply with state laws and regulations related to workers comp insurance.
    • State Government Insurance Boards: State governments play a key role in regulating workers comp insurance and enforcing state laws and regulations related to coverage and benefits. State governments also administer state funds for workers comp insurance and may provide additional resources and support to injured or ill employees.
    • Attorneys: Attorneys may be involved in workers comp insurance claims if an injured or ill employee seeks legal representation to help them navigate the claims process, challenge a denied claim, or pursue legal action related to their injury or illness.

Customer Sales Types

There are 4 common customer scenarios your sales team will encounter when an employer needs to discuss healthcare insurance:

  • New to Workers Comp: As workers comp is required in most states after an employer’s first employee, these are most likely going to be businesses that are entirely new to payroll.
  • Workers Comp is through Payroll: One of the primary ways to pay for workers comp is to use Pay-As-You-Go (“PAYGo”) reporting based on your actual payroll, which improves cash flow for the employer. Additionally, it is relatively easy to move over a workers comp plan by issuing a Broker of Record transfer. As such, ADP, Paychex, Gusto, and many payroll providers encourage their sales representatives to push workers comp insurance on every payroll sales opportunity, making this a common way that employers have existing workers comp insurance. An employer who has their workers comp through their payroll insurance brokerage will want to have their new payroll provider incorporated with a PAYGo payment structure too to maintain their current policy.
  • Workers Comp is through Independent Broker: Many payroll prospects will have their workers comp through their general business insurance broker who is also covering their General Liability, Commercial Property, and even Auto Insurance. These workers' comp plans are typically not offering PAYGo because they are unable to access the required payroll data, so there is an easy value prop your sales representatives can position immediately. The main objection here is that a SMB prefers to have all of their insurance services through one point of contact, but after a high yearly audit or during plan renewal an employer will be more open to reviewing their options.
  • Workers Comp is through a Professional Employer Organizations (PEO): The employer is “leasing” their employees from a PEO, meaning that all employee services (benefits, payroll, and other HR services) are provided through the PEO rather than the employer. These are by far the hardest to transfer over to your platform because you need to offer several other products. However, because PEO’s typically have a very risk averse profile, they will not underwrite every business workers comp plan that is on their PEO. Workers comp is also tied to the total payroll amounts, which an employer is still being charged via leasing, so an employer can retain their overall business insurance broker’s workers comp plan and still be on a PEO. It is critical when you encounter a PEO that you review every line of business that a PEO offers to see which a prospect is using, and which you can bring over with them after moving off of the PEO.

Of the above, you should primarily focus your GTM around new workers comp plans and workers comp plan Broker of Record switches, doing your best to avoid PEO scenarios. If a business is starting payroll for the first time, your sales reps should always push your workers comp solution as an assumed packaged opportunity. For all other scenarios, the employer should already have a workers’ comp policy established so focusing on the value positions your solution delivers as well as how easy it is to switch Broker of Records should dominate your communication towards your clients.

Selling Workers Comp

This section will empower your sales representatives to ensure they are capturing the maximum amount of workers comp cross-sells as possible.

Note that this guide assumes that you do not have any existing licensure to sell workers comp insurance and that you are only selling to workers comp prospects who are interested in running or currently live running payroll.

How to generate interest in your workers comp offering

What should your messaging be?

Prospects who already have PAYGo workers comp insurance will understand the value of making you the Broker of Record for their existing insurance; namely, this BOR transfer will allow them to keep their existing policy in place while moving to your payroll platform. The messaging in these situations is therefore (1) that you have the ability to offer PAYGo workers comp insurance and subsequently (2) all the key benefits of why your payroll offering is better than other offerings.

Thus, the vast majority of the messaging you will be focused on for workers comp concerns the value of moving off of a yearly audit payment plan to PAYGo. Note that a Yearly Audit plan can often be converted to a PAYGo plan in the middle of the policy term length, so always push the merits of transitioning to a PAYGo plan facilitated via your payroll product regardless of the existing plan the customer uses.

PAYGo workers comp insurance is considered superior to traditional yearly audits for several reasons:

  1. Accurate, Real-Time Premium Calculation: With PAYGo insurance, premiums are calculated based on actual payroll data. This ensures that the business pays the correct premium amount in real-time, reflecting their current payroll and employee classifications. Traditional yearly audits, on the other hand, rely on estimated payroll figures, which can result in overpayment or underpayment of premiums. Pay-as-you-go eliminates the need for manual estimations and provides more accurate premium calculations.
  1. Cash Flow Management: PAYGo allows businesses to spread their workers comp premiums throughout the year, instead of making large upfront payments or facing a substantial year-end audit bill, businesses pay smaller, more manageable premiums based on actual payroll data.
  1. Minimized Audit Adjustments: Yearly audits in traditional workers comp insurance often result in adjustments based on discrepancies between estimated and actual payroll figures. These adjustments can lead to unexpected premium increases or refunds. Pay-as-you-go eliminates the need for significant audit adjustments since premiums are based on real-time payroll data. This reduces the administrative burden and potential financial surprises for businesses.
  1. Administrative Efficiency: Traditional yearly audits require businesses to collect and compile payroll data, submit reports, and undergo a time-consuming audit process. Pay-as-you-go simplifies the administrative tasks associated with workers comp insurance. Payroll data is seamlessly integrated with the insurance carrier's system, reducing paperwork and streamlining the premium calculation and payment process.
  1. Improved Accuracy and Compliance: Pay-as-you-go helps businesses maintain accurate and up-to-date workers comp records. Since premiums are calculated based on actual payroll data, businesses are less likely to underreport or misclassify employees, which can lead to compliance issues and penalties. Pay-as-you-go promotes better record-keeping and compliance with workers comp regulations.
  1. Flexibility and Scalability: Pay-as-you-go offers businesses flexibility and scalability as their payroll fluctuates. It can easily accommodate changes in employee count, wages, and job classifications. This scalability is particularly beneficial for seasonal businesses or those experiencing growth or fluctuating workforce sizes.

How should we raise the visibility of our workers comp offering in conversation?

For payroll prospects: With the clear value propositions listed above, the payroll sales representative should end every closed-won payroll sales opportunity with:

"Do you want to incorporate pay-as-you-go workers comp with your payroll? There's no cost, it takes one quick signature, and [INSERT VALUE PROP] [example:]it prevents a large premium payout during your audit.”

This opening pitch will prompt either a quick yes or a specific objection, which Check recommends you log into your CRM. However, the most important follow up question to a hard no from a prospect is “when is your workers comp plan renewal? I would love to show you our options then.” This question allows your marketing team and sales representatives to segment your payroll based on future campaigns.

For existing payroll customers: Having your payroll contact reach out regarding your plan is not surprising to an employer given the tight relationship the two systems have. The primary talk track for existing payroll customers is:

“I am reaching out to discuss our pay-as-you-go workers comp offering. There's no cost, it takes one quick signature, and [INSERT VALUE PROP] [example:]it prevents a large premium payout during your audit."

The objections your sales representatives will have with existing payroll customers match what new payroll customers will say and the follow up question of renewal is applicable too.

How should we raise visibility of our workers comp offering in our product?

For payroll prospects: Employers know the connection between payroll and workers comp. Hosting a public facing page dedicated to your workers comp product outlining the value points above with a Call-to-Action to speak with a payroll sales representative will help drive overall payroll sales.

For existing payroll customers: We recommend you either 1) Add an “Insurance” tab into your core product website or 2) Add an Insurance section on the Payroll page in your core product. Both options should outline the value points above, with option #2 being much more abbreviated. Both options should have a Call-to-Action of integrating their payroll with a PAYGo plan.

Campaigns & lead generation strategies built around workers comp

For all payroll prospect marketing campaigns, we recommend that you briefly mention one of the above value points in any outreach to remind payroll prospects that you have this offering. A good example is the following: “Our payroll offering plus integrated benefits like Pay-as-you-Go Workers Compensation… [rest of statement about your key payroll differentiators].”

Regarding dedicated marketing campaigns for workers comp to existing payroll customers, we recommend that you primarily target customers with content 1-2 months prior to their workers comp renewal date. This content should be both email and in-product via strategically positioning banners, pop-ups, and other product-leg growth options to directly prompt your payroll customer to switch their workers comp policy to one that runs through your payroll system.

In between surfacing workers’ comp to payroll prospects and months before current payroll clients policy renewal date, you should send soft reminders of your workers comp offering 4 to 8 times per year (roughly, every other month to every month excluding the renewal period). This content should mainly be added to other current payroll customer engagement content but can be a dedicated campaign as well.

The main input into how often and how directly you should market workers’ comp to current payroll clients depends on how many other competing products you have to market; higher product count should include workers’ comp along with other secondary product marketing, while lower product count can have more worker’s comp specific marketing.

How should my strategy take advantage of any seasonality?

Businesses will purchase their workers' comp plan either when they first form their business entity along with their other insurance services or when they hire their first employee. Therefore there are no seasonal considerations to workers comp outside of the renewal period.

This lack of seasonality is the core reason why it is so imperative that your sales representatives are asking and logging renewal dates into your CRM so you can drive targeted campaigns that are relevant to each customer throughout the year.

What fields should I add to my CRM to capture relevant health information?

The more data you can add to your CRM for payroll and the connected systems, the more effective a sales motion you will have. By adding these select fields to your CRM you can target customers with data-driven outreach campaigns, keeping your messaging relevant and moving clients through the sales funnel more effectively.

Fields to add:

  • Is your workers comp plan through your payroll provider, local broker, or a PEO?
    • Payroll provider
    • Local broker
    • PEO
  • Do you have a Pay-As-You-Go (PAYGo) workers comp payment plan or a yearly audit payment plan?
    • PAYGo
    • Yearly Audit
  • When is your workers comp plan renewal date?
    • Calendar date selection.
      • Most employers will say just the month, so reps can select the 1st of whichever month the employer responds with.

Knowing these aspects of your clients will allow your sales team to create dynamic and focused outreach strategies to drive high workers comp attach rates.

How to move from interest to sold

What should my GTM motion look like?

Our recommended health GTM motion can be found in this Whimsical diagram. This offers step-by-step guidance for how to navigate different types of workers comp insurance prospects from initial interest through deal completion.

How should I train my reps to sell Workers Comp?

Check offers out-of-the-box How to Sell Workers Comp training for reps that can be issued via Trainual. Please reach out to Check with which reps you would like to assign the training to.

What are common disqualifiers we should look for?

If a client simply needs a new Broker of Record to switch off their current payroll provider onto your system, then an insurance carrier has already opted-in to underwriting their workers comp policy and there are no DQ considerations your team needs to assess.

If you have a prospect who is needing a new workers comp policy or is in a renewal period, there are a couple of considerations you should keep in mind prior to guaranteeing the prospect can utilize your workers comp solution.

  • Industry Classification: Some industries, such as construction or manufacturing, are considered higher risk due to the nature of the work involved. Be sure to understand which industries your workers comp strategy may not support.
  • Claims History: Inquire about any previous workers comp claims, including the number of claims, severity, and frequency. A history of frequent or severe claims may indicate higher risk or poor safety practices.
  • Hazardous Activities: Certain activities, such as working at heights or handling hazardous materials, can increase the risk of workplace injuries. More dangerous occupations will require a longer timeline of receiving carrier quotes back for review.
  • Coverage Requirements: Some businesses may require additional coverage options or endorsements based on their operations or contractual obligations.

The workers comp broker model you decide to move forward with will inevitably be the decision maker on these critical considerations.

How should reps handle questions that they cannot answer?

Non-licensed sales representatives for workers comp may not be legally allowed to provide specific details or answer certain questions related to policy terms and coverage. These questions typically require expert knowledge and licensing to ensure compliance with insurance regulations.

If a sales rep gets asked questions around any of the areas listed below, their response should be “Workers comp is a licensed insurance policy, and I cannot legally provide you those answers. I will take down all of your questions and have my licensed workers comp broker respond back to you shortly.

What regulatory traps should I avoid?

Here are some examples of questions that a non-licensed sales rep may not be able to answer:

  • Policy Exclusions: Questions about specific exclusions within the policy, such as activities or circumstances that are not covered by the insurance, requires detailed knowledge of the policy terms and conditions.
  • Policy Limits: Questions about the specific coverage limits and sub-limits within the policy requires an understanding of the policy structure and the business' unique needs.
  • Claims Handling Process: Questions about the specific claims handling process, including reporting procedures, timelines, and dispute resolution, requires knowledge of the insurance provider's internal policies and practices.
  • Legal Compliance: Inquiries related to the legal compliance aspects of workers comp insurance, such as the classification of employees, state-specific regulations, or reporting requirements, requires an understanding of local labor laws and insurance regulations.
  • Premium Calculation: Questions about the factors influencing premium calculations, such as experience modification factors, payroll audits, or rating classifications, requires a deeper understanding of underwriting principles and industry standards.

It's important to note that the limitations on what a non-licensed sales representative can answer may vary depending on local laws and regulations. In some jurisdictions, there may be stricter regulations regarding the information non-licensed representatives can provide. Therefore, it is always advisable to consult a licensed insurance professional for accurate and detailed information regarding workers comp policies.

What should commissions look like?

For payout of your sales representatives, Check recommends a flat fee of $150 / plan setup on our workers comp strategy. This dollar amount is significant enough that it will motivate a sales rep to ask about workers comp on every payroll deal, but small enough where they won’t push closing the opportunity too much. It also provides reps with straight forward commission math. If they sell 10 deals a month and half add on workers comp, they just made $750 of extra commission for very low lift.

Appendix: Workers Comp Insurance 101

What is workers comp?

Workers comp insurance is a type of insurance policy that provides benefits to employees who are injured or become ill as a result of their job. This insurance policy is designed to protect both the employer and the employee by providing financial assistance to cover medical expenses, lost wages, and other related costs.

Workers comp insurance is typically required by law in most states in the United States. The regulatory required coverage provided by a workers comp policy varies depending on the state, but typically includes benefits for medical expenses, disability payments, and rehabilitation costs.

What is a workers comp insurance premium and how is it calculated?

A workers comp insurance premium is the amount of money that an employer pays to an insurance company to provide coverage for work-related injuries and illnesses. The premium is based on a number of factors, including the size and type of the business, the industry the business operates in, the number of employees, the company's claims history, and the state in which the business operates.

To calculate the premium, the insurance company will typically use a formula that takes into account the company's payroll, the type of work that employees do (referred to as Class Codes), and the company's past workers comp claims. The premium is usually calculated as a percentage of the company's payroll, with the exact percentage varying depending on the type of work that employees do.

How is workers comp insurance connected to payroll?

Workers comp insurance premiums are often connected to payroll because the premium is typically calculated as a percentage of the employer's payroll. This is because the amount of payroll an employer has is often a good indicator of the number of employees they have and the amount of risk associated with the work they perform.

The premium calculation takes into account the classification code assigned to the employer's business by the state's workers comp insurance rating bureau. Each classification code has a different rate based on the perceived risk of injury associated with the type of work performed. The rate is then applied to the employer's payroll to determine the premium.

The difference between pay-as-you-go (PAYGo) and yearly audit workers comp insurance

Pay-as-you-go workers comp insurance and yearly audit workers comp insurance are two different methods of premium calculation and payment for workers comp insurance policies.

Pay-as-you-go workers comp insurance allows businesses to make premium payments in real-time based on their actual payroll amounts. With this method, businesses typically work with a payroll provider or insurance carrier that integrates workers comp insurance premiums into their payroll processing. This allows businesses to make payments based on their actual payroll amounts, rather than paying a lump sum at the beginning of the policy term. This method can help businesses manage their cash flow and avoid unexpected premium adjustments at the end of the policy term.

Yearly audit workers comp insurance, on the other hand, requires businesses to estimate their payroll amounts at the beginning of the policy term and make a lump-sum payment for their workers comp insurance premiums. At the end of the policy term, an auditor will review the business actual payroll amounts and make any necessary adjustments to the premium payment based on the difference between the estimated and actual payroll amounts. This method can be more time-consuming and administratively burdensome for businesses, but it allows for a more accurate premium calculation based on actual payroll amounts.

Overall, pay-as-you-go workers comp insurance offers businesses more flexibility and accuracy in premium payments, while yearly audit workers comp insurance offers a more accurate premium calculation based on actual payroll amounts but requires more administrative work upfront and at the end of the policy term.

What percentage of a US business expenses is workers comp insurance?

According to the National Council on Comp Insurance (NCCI), the average workers comp insurance premium for all industries in the United States was $1.43 per $100 of payroll in 2020. This means that for every $100 of payroll, a business could expect to pay an average of $1.43 in workers comp insurance premiums.

 

The average cost of workers’ comp insurance falls between $0.75 to $2.74 per $100 of payroll.

Common Workers Comp PAYGo Objections

Employers may have several objections or concerns when considering moving their workers comp insurance onto a payroll provider's PAYGo offering. Here are some common objections and possible reasons behind them:

  1. Cost Considerations: One objection could be the perception that pay-as-you-go workers comp insurance might be more expensive compared to traditional annual premiums. Employers may worry that the convenience and flexibility of pay-as-you-go come at a higher price. However, it's important to note that the costs of pay-as-you-go insurance can vary depending on factors such as the size of the workforce, industry classification, and claims history. Employers should carefully compare the costs and benefits of different insurance options to assess the overall value.
  1. Loss of Control: Some employers may have concerns about losing control over the workers comp process by entrusting it to a payroll provider. They may prefer to maintain direct relationships with insurance carriers and manage the insurance process independently. This objection can be addressed by selecting a reputable payroll provider with a track record of efficiently managing workers comp and ensuring effective communication and transparency between all parties involved.
  1. Integration Challenges: Employers may worry about the technical complexities of integrating payroll and workers comp systems. They may have concerns about data accuracy, compatibility issues, or the potential disruption to existing payroll processes. It is crucial to choose a payroll provider that offers seamless integration with workers comp systems, provides comprehensive support during the implementation phase, and addresses any concerns or technical challenges that arise.
  1. Perception of Limited Insurance Options: Some employers may believe that a payroll provider's pay-as-you-go offering restricts their options to a single insurance carrier or a limited pool of choices. They may prefer the flexibility to select their own insurance carrier based on their specific needs and preferences. However, it is essential to clarify with the payroll provider whether they offer multiple insurance carrier options or if they have exclusive partnerships with specific carriers. Many payroll providers can still offer a range of insurance carriers, allowing employers to choose the coverage that best suits their requirements.
  1. Quality of Service: Employers might be concerned about the quality of service provided by a payroll provider's workers comp offering. They may question whether the payroll provider has sufficient expertise in managing claims, providing timely support, or advocating for their interests in case of disputes. Addressing this objection requires conducting due diligence on the payroll provider, evaluating their experience, reputation, and customer reviews related to their workers comp services.
  1. Compliance and Risk Management: Employers may have concerns about maintaining compliance with workers comp regulations and effectively managing risk when transitioning to a pay-as-you-go model. They may question whether the payroll provider has the necessary expertise to ensure compliance and handle risk-related aspects effectively. Employers should assess the payroll provider's capabilities, inquire about their risk management strategies, and seek assurance that they can navigate compliance requirements in the workers comp domain.

It's crucial for employers to engage in open discussions with the payroll provider, clarify any concerns or objections, and seek detailed explanations and evidence to address their specific reservations. This allows for a better understanding of the benefits and drawbacks of moving to a pay-as-you-go workers comp insurance model and helps employers make informed decisions.

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Last updated on June 6, 2025