Best Strategies in Approaching the Large Group Sale

By Chris Della Sala

When it comes to “large group business,” the scope and scale of what you are about to tackle may seem daunting. The reality of the situation is that there is often a great deal of overlap between large and small group characteristics when it comes to employee benefits. Additionally, there are varying degrees of definition when it comes to “small group” and “large group.” Sometimes the definition may be over 50 lives, to be consistent with certain Affordable Care Act (ACA) provisions, but other times it might be 100 lives, 500 lives, or even 1,000+ lives, depending on the insurance carrier or consultant involved. Regardless, there is no doubt large group business requires careful consideration, meticulous evaluation, and the highest levels of professionalism. If you are in the benefits space and currently manage “small group” business, you have the skill set to sell “large group” business as well.


There exist commonalities in how small and large companies evaluate employee benefits offerings and manage the administration thereof,but there are also obvious differences. Large businesses are often focused on issues such as:

  • considering how a benefits portfolio will impact their competitiveness in an increasingly competitive landscape
  • how to attract and retain top talent, and
  • how to promote and sustain employee

Additionally, due to the law of large numbers, large businesses have both the capacity and need to focus on large-scale financial aspects of insurance, such as how much they are spending per employee per month (PEPM) on insurance contributions and other additional resources like ACA reporting, COBRA administration, benefits enrollment technology and other relevant services. There are vendors out there with unique business models that offer the ability to provide such solutions without paying high PEPM costs, you just need to know where to look.

Ask your carrier reps which partners they leverage to provide no-cost solutions of such services. Employers with larger employeepopulations often incur significant financial impacts when paying for solutions like these at market value.

If you are in the benefits space and currently manage “small group”business, you have the skill set to sell “large group” business as well.

Smaller businesses, on the other hand, tend to be more focused on individual employee concerns such as how a serious illness might impact key employees, tax incentives and employee workload. Oftentimes there is an inherent workload restriction on small business operators and administrators — it is quite common to have a single person handling benefits, human resources, payroll, office management and more. In these situations, it is very easy for those individuals to become overwhelmed when talks of change to their existing day-to-day functions or benefits strategy are introduced.

Furthermore, in today’s COVID-19 environment, all sizes of companies are adapting to accommodate a remote work force and promotehealthy living — a transition that has been rapid and new to many. In either scenario, showing empathy toward the administrators position and workload goes a long way. Serving as a resource, offering solutions, and illustrating in a clearly articulated way how you can relieve them of a burden of work and responsibility without jeopardizing their perceived value to the company will always win you big points.


Large groups have unique needs, not canned requirements. Be attentive and responsive. Some of this may seem like common sense, but here are a few tips:

  • When it comes to closing large group business, whether it is a case with 50 lives, 100 lives, or 2,000 lives, there are a few critical elements that one should always consider. First, you must position yourself as an expert that is readily available to do everything in your power to be an advocate and resource to them. Providing value is the most important element to this aspect of large group sales. Share your expertise in dealing with sophisticated business strategies, budget management and cost savings solutions, and ultimately having a thorough understanding of the human resources world as it pertains to employee benefits.

Large groups have unique needs, not canned requirements.

  • Discovery is critical. The more you ask, the more you know. The more you know, the more helpful you can be. By understanding their goals and concerns, you can identify their challenges and offer valuable solutions. Understanding your clients’ world — where they spend their time, what needs they have and what challenges they face — will help you not only build rapport, but also generate a method to deliver helpful solutions as you create a proposal.
  • During the discovery meeting, your goal is to listen, listen again, and listen some more. I often equate it to the 80/20 rule — spend 80% of your time listening and the other 20% asking Allow the person you are meeting with to do most of the talking. Do not “show up and throw up,” as I once heard a mentor of mine say. If you do not have a thorough and consistent discovery document, I highly encourage you to develop one immediately — one that is transferable for all prospect types. And one that captures all the data you need to evaluate whether a prospect is a good business opportunity or not. Let’s face it, not all opportunities are good ones. And that is another critical element of the large group world — know when to walk away and have the courage to do so. When you attempt to onboard a new client that is not a good business fit, everyone loses. Do not subject your client to disappointment, or worse, damage your company’s reputation. Be brave — walk away when it is justified.

Let’s face it, not all opportunities are good ones. And that is another critical element of the large group world — know when to walk away and have the courage to do so.

  • Be prepared and do your diligence on the opportunity. Invest time researching and educating yourself about the people and company you are meeting with. Know who their key employees are and their respective roles. Understand their brand and culture. Use language from their mission and vision statements in your proposal and during your meetings. Be professional, be knowledgeable and be sincere.
  • Once your discovery is complete, make sure to establish concrete next steps and timelines. You should never leave any meeting or end a phone call prior to clearly outlining next steps. This is pivotal if you are to maintain the momentum needed to close or disqualify the opportunity. I always encourage my sales team members to look for ways to disqualify an opportunity. While it might seem counter intuitive, it is critical and accomplishes several things:
    1. It will help you narrow your focus, so you are spending time on real opportunities.
    2. It helps you identify opportunities that will benefit greatly from the services you provide, creating a win-win all around.
    3. Lastly and arguably most importantly, adopting this approach will help you position yourself as someone who truly cares as opposed to someone focused solely on the sale. Distinguish yourself from others — this can be your greatest asset. When presenting your solutions, tailor your solutions to the prospect’s specific needs as identified during the discovery and position your solutions to fit their needs. And when you say you are going to do something, do it and do it well.

Ultimately, in its most basic form, winning a large case sale comes down to this:

  • Be professional. Though it sounds like common sense, professionalism spans the gamut from communications, to attire and behavior.
  • Seek mentorship. If you truly want to delve into the large group market, seek guidance from those who know the market well and are willing to help you grow.
  • Perform your due diligence. There is no excuse for going into a meeting unprepared. Spend time researching the prospect’s culture, mission, vision, and values. Leverage resources like MiEdge or the company’s website to identify their current employee benefits offerings.
  • Discovery is critical. Develop a discovery document that can be used for all prospects and use it consistently. Ask detailed questions and obtain a thorough “image” of their employee benefits offering, how they manage benefits and human resources, etc. Ask and listen. Remember the 80/20 rule.
  • Focus on cost savings. Find ways to provide cost savings through tax mechanisms and leveraging partnerships with insurance carriers and vendors that provide no-cost solutions like COBRA administration, ACA reporting and benefits administration.
  • Know when to walk away. Have the courage to walk away from business that is not a fit, people that are difficult, or businesses that you cannot be a valuable resource to. Look for ways to disqualify an opportunity. It is not all about the dollar, you risk more than losing a sale.
  • Establish agreed upon, concrete next steps and timelines before ending every meeting.
  • Next time you find yourself entertaining a large group prospect — territory that you may or may not have explored before — leverage these tools and guidelines and you stand a good chance of landing the deal. Without a doubt, you will know with confidence you at least put your best foot forward.

CHRIS DELLA SALA serves as the VP of sales at TBX®, an enrollment technology firm specializing in no-cost, contactless, self-serve enrollments. Chris recently joined TBX® after more than 8 years at Colonial Life, where he served in various capacities, including leading the Southern California, Orange County-based sales organization and being the large-group practice leader for the Southwest U.S. His vision for TBX is to serve as the premier broker partner, go-to technological enrollment platform, and ultimately disrupt the industry’s mindset on enrollment technology and capabilities. Originally from Texas, Chris currently resides in Irvine, California. He can be contacted at Chris@