Check’s Health Insurance Go-to-Market Playbook

Adding a health insurance option is an exciting new step in expanding your payroll strategy. Selling health insurance effectively will both help you unblock core payroll sales opportunities as well as significantly expand the total revenue you see from payroll customers. However, health insurance is a complex offering involving multiple stakeholders and representing one of the largest expenses an employer has. Preparing your sellers and nailing your health Go-To-Market (”GTM”) will be critical to the success of your health offering.

This playbook provides Check’s prescriptive guidance for selling health insurance. We will cover several key GTM areas, including:

Note: for the purposes of this document, we have assumed that you have prior knowledge on different types of healthcare benefits, and in particular fully-funded, employer-sponsored group health plans. Please see the Appendix for greater detail on the specifics of different health offerings.

There are a number of stakeholders in the healthcare landscape that interact with the employer purchasing health, including the health insurance carrier, the healthcare benefit broker, and the benefit administration platform. The relationship between an employer and these other stakeholders is highly interconnected and critical to the success of the employer's health benefits program.

The health insurance carrier is the entity that provides the actual healthcare coverage to the employer's employees. The employer selects the carrier based on the plan options and pricing negotiated with the help of their broker, and the carrier administers the plan and pays for covered healthcare expenses.

The healthcare benefit broker acts as an intermediary between the employer and the health insurance carrier. They help the employer understand the different plan options available and negotiate favorable terms and pricing with the carrier. The broker may also provide ongoing support and assistance to the employer and their employees throughout the enrollment process and during the plan year.

The benefit administration platform is the technology solution used by the employer to manage their healthcare benefits program. It allows the employer to enroll employees, manage plan options, track employee contributions and claims, and access reporting and analytics on plan usage and cost. The platform may be provided by the health insurance carrier, the benefit broker, or a third-party vendor.

Together, these entities work collaboratively to design and manage the employer's healthcare benefits program. By leveraging the expertise of their broker, utilizing a modern benefit administration platform, and selecting the right health insurance carrier, employers can provide high-quality healthcare coverage to their employees while effectively managing costs and administrative burden.

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

This section will enable you to develop a GTM strategy that effectively communicates your health value proposition and sell to customers who want benefits while remaining in compliance in the regulated health benefits market.

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

The primary messaging we recommend is how adding health benefits can attract and retain talent. Particularly for talent-competitive industries, offering health as an employer-sponsored benefit can allow the employer to stand out from the competition and get the best talent to come work for their team. As a secondary point, your messaging should also include that your benefits offering is compliant and is built to help them handle the overlap of health + payroll without them needing to be health benefits experts.

More broadly, there is also a more comprehensive, bundled messaging that you may consider around being a one-stop shop for all of a customer’s Human Capital Management (HCM) needs. This works particularly well if you also offer additional employee-related offerings on top of payroll and health benefits, as you can highlight health alongside a comprehensive suite of solutions. Note that this may not be the right strategy for everyone from the start of offering health benefits, but is one that you will mature into as you expand your payroll business.

For payroll prospects: We recommend that sales reps do light qualification during the payroll sales process. This can help identify potential customer requirements to sign with payroll and also create potential opportunities for downstream health sales. We recommend the following questions:

Offering benefits is such a large expense that has a significant impact on an employer’s talent attraction, most employers will have a quick answer on both of those questions. Both of the above answers should be added as fields to your payroll opportunity object in your CRM to allow you to do segmentation for future health benefits campaigns and outreach.

Note that Check does not recommend that you try to sell health at the same time as payroll. Because your reps are not licensed, they cannot negotiate pricing and handle other key economic factors related to health. The effect of trying to sell these together is that payroll deals get slowed down and potentially killed. Rather, we recommend you try to keep all health sales only to existing customers.

For existing payroll customers: If you have a customer success team that has regular engagements with existing customers, that team should ask “Are you considering any changes to your benefits offering?” every quarter, or in particular if they hear about challenges attracting and retaining talent or significant changes to hiring.

For payroll prospects: You should add a Benefits section into your website. Because payroll is required to use your health offering, we recommend that the Benefits lives as a section within wherever you highlight your Payroll offering.

For existing payroll customers: You should add a Benefits section into your product. Placement of this tab may depend on your overall product strategy, but we highly recommend it either lives as a section in the core product next to Payroll or a section in the Payroll product to raise the visibility of the benefits offering.

This section should contain the following information:

Additionally, when you run marketing campaigns related to health, we highly recommend using in-product features to call attention to those campaigns. Utilize product banners, pop ups, or other product-led growth options on the payroll homepage as well as the page where customers can add / update benefits and post-tax deductions.

Outside of Open Enrollment, running outbound campaigns specifically for health should be used modestly. The reason for this is that outside of that period, there are only two types of health sales opportunities: (1) accounts who have benefits through another payroll provider and want a Broker-of-Record transfer as they switch payroll providers, and (2) accounts who are entirely new to health. In both of these buckets, they are aware of the benefits of health generally, so your goal with marketing to these groups is to raise awareness of your benefits offering and allow prospects to self-identify, rather than drive hard adoption. Otherwise, too hard of a marketing push may slow down your payroll sales motion.

We recommend running outbound campaigns to both groups in the following scenarios:

We would recommend you target specific sub-segments of groups 1 + 2 above. Common characteristics include:

Similar to Payroll Selling Season, the majority of your clients that have healthcare benefits or are considering benefits will be reviewing plans and signing up for / making changes to their healthcare insurance coverage. This period is known as “Open Enrollment” in the health industry and for most companies happens in calendar year Q4.

We recommend a dedicated campaign that is themed around Open Enrollment. The outreach of this campaign should be segmented into the following 3 groups:

The stickiness of benefits and payroll together, along with the possible revenue capture for your platform justifies the sequenced, multi-touch outreach. Additionally, this is a once-a-year campaign that coincides with the same period that a significant portion of your clients will be moving benefit plans.

Much like adding new fields to your CRM for payroll, 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:

The rest of the fields assume they answered YES to the first question

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 health benefits prospects from initial interest through deal completion.

Check offers out-of-the-box How to sell health benefits 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.

You should record demo videos of the applicable benefit administration platform and make those available for sales representatives to showcase. We recommend that those be accompanied by a one-pager of the key benefits of your solution. We recommend having the rep play through the demo video and walk through key points.

No matter which benefit strategy your team selects, it is important to have your sales representative let the client know that they are not a licensed broker and their talk track is guidance-only, not official responses.

The only common disqualification you should be aware of is that an employer must have 2 or more full time employees (with at least one employee who is not a co-owner or spouse) to be eligible for small group health.

Note that your disqualifications may vary depending on your customer focus and benefits strategy. An example of this is if your platform also serves agricultural clients. In those cases, because administration is difficult for seasonal employees, we would recommend that you only satisfy the office administration staff of an agriculture organization or avoid agricultural clients altogether.

Unless your team hires or certifies a licensed health insurance broker, there are a number of actions any non-licensed team member legally cannot do with a health prospect:

If a client is insisting that a sales representative answer directly to any of the questions above, it is imperative that the sales representative keeps to the stance that a licensed broker must answer those questions and that they can only provide guidelines. This response is not only the best legal response, but also provides the client with the trust knowing how seriously your organization takes healthcare benefit decisions.

If any of the above scenarios occur, Check recommends that your reps use the following script to avoid answering those questions but to keep the opportunity alive:

"I cannot answer that question due to regulatory licensing requirements. The best path forward is to connect you with one of our broker partners who can answer this and other detailed questions you have. What time this or next week can I connect you with my broker partner?"

Price conversations are one of the specific regulatory traps a sales representative should not address. However, a licensed broker will be able to provide you ball park figures on different benefit packages. If pressed for benefit pricing, a sales representative can respond with “Providing benefit pricing requires a licensed broker. However, our healthcare partner shows monthly plans starting at $276 per employee per month.” Ask your broker for more details on those numbers.

When discussing sales rep compensation, it is always important to remember that sales representatives are very good at finding the ability to maximize their payout with the least amount of effort.

For this reason, Check recommends having your benefit strategy in motion for ~6 months before determining the type and amount of rep compensation. The reason for this is to better understand what types of clients want to attach health through your platform before paying out reps. This will ensure that adding health to a reps’ book of what they can sell does not cause (e.g. never selling health, aggressively pushing health, etc.).

During this period, we recommend a flat SPIF equal to 25% of the annual health revenue you would get at an average customer. So, if you get $7 per enrolled employee per month, and your average customer has 10 employees, the SPIF would be 25% * 10 employees * $7 PEPM * 12 months = $210.

Over the long-term, you will need to determine your own payouts based on the adoption you are seeing. Industry best practices have sales reps paid out at a rate of anywhere from 20-40% of a deal’s expected year 1 revenue from healthcare benefits. Compare what these commissions are relative to commissions for other products to ensure that you aren’t creating perverse incentives by introducing health sales.

Employer-sponsored group health insurance plans are health insurance policies that are purchased by an employer on behalf of a group of employees. These plans are typically offered as part of an employee benefits package and may provide coverage for the employee, the employee's spouse, and dependents.

Group health insurance plans can be customized to meet the specific needs of the group. Employers or organizations may be able to choose from a variety of plans with different levels of coverage, deductibles, and co-payments. They may also be able to choose from a range of insurance providers.

All group plans have the same key elements, all of which you are likely familiar with from your own health coverage:

There are two common types of group health insurance: small and large. Small-group health insurance is typically purchased by businesses with 50 or fewer employees in most states, except for California, Colorado, New York, and Vermont, where plans are available to businesses with up to 100 employees. Rates and coverage for small group health plans are set by the state, meaning that small businesses cannot negotiate premiums with insurance companies. Small businesses often pay more for the same health insurance coverage than larger businesses, which is a top concern for small business owners and can make it difficult for them to provide coverage for their employees.

Large group plans are generally preferred by businesses due to their lower cost for the same coverage, but they are only available to businesses with 51 or more full-time equivalent employees in most states. A full-time equivalent employee is defined as someone who works an average of at least 30 hours a week.

It is important to consider the type of healthcare plan when selecting a healthcare plan for a business because it can significantly impact the cost and quality of healthcare coverage provided to employees.

There are also other options available for offering health that are not group funded. A few common ones include:

Which plan type an employer selects can have a significant impact on their profits given the high costs of benefits.