Selling to Employers: Win Rate (Part 5)

Boosting your win rate using by using an empathic approach: listen, tell stories, align incentives, make your product easy to understand and implement

This article is part of a six part series written by Ryan Russell at HTN sharing his learnings on employer sales. Click the links to jump to any of the other articles in the series:


We’re going to spend this section talking about what I view as the most important element of winning over employers: empathy. 

You are selling to people whose job it is to think about how to keep employees healthy, happy and productive. If you cannot put yourself in your buyers’ shoes (and of their employees), you might as well pack up and go home. Even if your product is killer, employers are conditioned to be skeptical.

These buyers are not only required to embody the thinking, emotions and reactions of their employees but also balance the cost and operational headache of managing all other benefits and related systems. Because empathy is such a critical part of their job, you either need to commit to an empathetic approach or hire people that will. 

What does that mean? It means that empathy needs to be a wrapper around all of the interactions and engagements you have with these types of buyers. Here are a few components of taking this approach, which we’ll get into below:

  • Talk less, listen more (see Qualified Leads section)

  • Tell your story with stories

  • Align incentives and put your money where your mouth is

  • Make your product easy to understand and communicate to others

  • Make your product easy to implement 

Tell your story with stories

Stories are 20x more likely to be remembered than facts. They connect, engage and appeal to people on an emotional level.  Remember, these are folks who deal with people all day long and if they believe an employee will “love the benefit” that is likely more valuable than the cost savings they are skeptical about. A thank you note to the CHRO from an employee will be shared with the whole team. 0.4% of annual cost savings will be viewed as a rounding error and forgotten about. 

Only once they’ve made that emotional connection is it time to connect it to the business priorities. I’ve found when I do that, a few things happen:

  • You have an invested advocate who personally wants to see this succeed

  • That person has a narrative they can easily, and are excited to, carry forward to other stakeholders like the CHRO or CFO 

  • You can always remind the team about the purpose and goal through the stories 

  • How do you incorporate that into Velocity? Ask what stories your contact has shared with his/her boss and track it.

Crafting a Good Story

It is hard to craft stories that aren’t too long and resonate with your entire audience. A simple, easy framework to start with is Freytag’s Story Pyramid. This framework is what you would remember from elementary school. A beginning, a middle, and an end with places that tug on your emotions. It seems overly simplistic but if you take a look at your current pitch deck, could you tell me where you have a story arch that has these basic components? 

Freytag's Story Pyramid. Source:

The goal of telling a story like this is to have the benefits person you’re pitching saying: “oh yeah, that happened to me, or my daughter, or an employee of ours. And yes, I can absolutely see how your product would make that terrible experience better.” If you can elicit that response, you’ve made an emotional connection that he/she is invested in and it makes you a real person, not just a salesperson. A story offers common ground to establish a personal and emotional connection.

It can often feel easier or more appropriate to put together a bunch of stats and charts. Don’t get me wrong, “proof” or data is still absolutely necessary to make your case and different types of proof are required at different stages.  But you can weave them in to support your story. So challenge yourself to test storytelling and don’t be afraid to try different stories. There will undoubtedly be some that fall flat or audiences that say “just tell me what your product is” - trust me, I know from experience but you will be able to test and learn. 

In all likelihood your best salespeople are already telling their own stories and just don’t realize it – tap them or other natural storytellers in the org to use their stories. There is a reason people tell stories to each other in passing and binge Netflix shows to then tell friends about. We like stories, we remember them and we like to retell them. 

This Hinge Health slide deck provides a good example of where / how a story shows up. It’s the simplest slide in the entire presentation - a picture of a real person and a couple of words emphasizing the story. While we don’t know exactly what the voiceover was during the conversation, it pretty clearly is a personal story about the folks on the page, including rising action and climax of a potentially life altering problem, and a resolution with Hinge helping to solve the problem. You can bet this story is one that the benefits team could connect with emotionally. My only gripe is it shows up on slide five after some intro and credibility slides. If you are able to connect emotionally off the bat, might that open up the audience to engage more frequently throughout the discussion to get closer to the 40/60 talk listen ratio? Go back to Velocity - test different stories in different places and see what that does to outcomes.

Honing your stories based on an employer’s priorities

Part of the reason to try to make an emotional connection is that benefits teams have lots of priorities. While there is no doubt that digital health as a whole is a priority, the reality is the problem you are so focused on addressing may not be anywhere near the top of the priority list to the employer, or you might be focusing on the wrong problem.

Most digital health vendors I come across assume that managing cost is priority 1A for employer clients. Pitches commonly feature grandiose statements of the impact their solution can have in driving savings for employers. But this is a common fallacy because many employers either aren’t actually looking for digital health vendors to bend the cost curve or don’t believe they can because it is darn near impossible to tie savings back to specific vendors. 

At the end of the day, employer benefits teams and CFOs at employers are accustomed to healthcare costs rising. As this data highlights, costs consistently rise year after year. Finance is prepared to bake these cost increases into the budget on a yearly basis. Coming in promising to change that dynamic sets everyone up for failure. Again, put yourself in your benefits buyer’s shoes. As one employee benefits director put it:

“As long as we don’t increase trend, our CFO will be good. Either way, I’m not going to account for savings. I’d rather under promise and over-deliver, than overpromise and disappoint” 
– Sr. Director of Benefits

Let’s play out the cost savings narrative from some data that pregnancy app-maker Ovia Health attempted to quantify for an employer:


If I’m an employer, I might be looking at that analysis saying...

  • Okay, that’s 50,000 employees, but we have 15,000 employees and we skew older female so let’s say 2% instead of 3% birth rate… so that’s 300 deliveries

  • 25% engagement is conservative? We estimate 10-15% engagement with our consultants on benefits that people really, really love. So, at 15% that is 45 births engaging with Ovia.

  • I’ll take the 9.8%, even though our birthing claims don’t track quite to that, I think anyway... So, if we round up, that’s 5 pre-term babies.

  • Where did you get 20% reduction? Ohhh, your data… That’s probably cherry picked so I’ll conservatively give you 10%. So that’s 0.5 babies per year.

  • Okay, so that puts me at $39,000 savings per year using your $78,000 savings per pre-term birth

  • That equates to 0.04% of our $90M budget for claims (15k employees at $500 PEPM)

So while you are envisioning the prospect audience being wow’d by your product and results, the benefits person is really doing a full cost benefit analysis now using 0.04% as the anchor savings amount. 

They will let you keep talking about how your solution drives substantial cost savings, but they’re also thinking about all the other headaches that will come up in moving a program like this forward, including:

  1. Change management lift (e.g. stakeholder buy-in, comms, procurement, legal, security, etc.) 

  2. Potential negative employee reactions (fear of 1 angry employee email to the CHRO is a cost high enough to not do something) 

  3. The timing of other benefits priorities (e.g. implementing a new HRIS system)

  4. Adoption - if the uptake is low, is it worth the work?

A benefits buyer summed it up well saying “every solution creates its own problem.

At this point, you’ve already lost the sale without even knowing it. Never underestimate the power of inertia when working with employers - no HR team member is going to lose their job for choosing not to implement a new innovative benefit. They have a day job with a number of other priorities - without getting quickly to the relevant problem, you are going to lose your audience. 

Unless the VP of Total Rewards or CHRO has a mandate to cut $5M out of benefits spend by reversing an 8-year trend of 5% annual trend increases, cost savings may not really be your buyer’s real problem. Listen to figure out where you should be spending time. Also, ask yourself: is a story of a single family’s experience avoiding pre-term labor and that event reflecting well on the benefits team more impactful than 0.04% potential savings? 

Back to Velocity, ask different questions and test different ways to frame your core value prop to see what sticks - then track, test and iterate. 

Align incentives and put your money where your mouth is 

A friend of mine runs benefits at a mid-sized company. One day we were chatting about what it is like working for an employer benefits team hearing pitches from all these startups. Her response: 

“I have so many startups coming in giving me all these stats I already know. Then when I asked [Company A] about pricing, they started with a PUPM [Per User Per Month] fee, which I loved. However, then came the additional PEPM [Per Employee Per Month] fee - how can I justify that spend on something I don’t know works… just give me a PUPM fee and I’m in!” 

Now, many digital health vendors will justify additional fees because of the uncertainty in a PUPM fee. Remember from the Average Deal Size article that actually enrolling employees in these benefits is one of the most challenging parts of the sales process. Accepting a PUPM fee puts that risk squarely on the digital health vendor - if employees don’t become ‘users’, the digital health vendor doesn’t get paid. A PEPM fee has significantly less risk for the vendor as it has no enrollment risk. That said, we must remember, this is a full cost benefit analysis for the employer and putting skin in the game signals a self-belief in the product.

Here are few examples of different types of payment models with a range of risk sharing profiles:

IMPACT,(a payers and virtual-first providers coalition, put out a nice summary of different pricing options. While these are more specific to actual care delivery, they are a good illustration of how digital health startups can think about different approaches and the tradeoffs. 

One of the main considerations around risk is that actual outcomes can be really hard (or impossible) to separate and measure so it’s important to be clear on how that will be measured. For example, if you want to share in the savings you generate as a diabetes solution, what if the employer also has a weight loss vendor and most of the employees sign up for both solutions? Who gets credit?

So, while it can sound good coming from a startup to put skin in the game, many large employers are getting wise to this strategy and will try to use their leverage to avoid or change the arrangement. Being thoughtful about how to make it easy for employers to assess your effectiveness (whatever that effectiveness is), makes your buyer’s life easier as they approach the financial decision makers. Empathy. 

There are other ways to assess success as well - satisfaction scores, perceived health status scores, employee appreciation for offering the benefits. In the end, benefits are intended to help with productivity and retention, so how can you be creative about measuring those?

Regardless of what approach is taken, if incentives aren’t aligned between vendor and employer, it creates friction that can cause issues both during the sales process and long after. See, for instance, this conversation between the Health Service Board of San Francisco Health Service System (SFHSS), evaluating whether to renew a contract it had signed with Best Doctors for second opinions. The Board minutes from the discussion (see bottom of page 2), highlight some of the challenges that can come up when incentives aren’t aligned between vendor and employer. Specifically this note: 

Commissioners Breslin and Sass expressed reluctance in approving Best Doctors’ reduced 2019 renewal due to its high cost of over $1M, as well as Best Doctors’ avoidance in accepting responsibility for its opinions. Commissioner Breslin also expressed support for face-to-face opinions and consultations.

I imagine if you’re on the Best Doctors team, this is an objection that is concerning to see. And it highlights the challenge when your pricing model isn’t entirely aligned with your value prop to the employer. In this case, Best Doctors is pitching that an employee will get a quality second opinion via their service, which in turn, will help employees receive better care. But Best Doctors isn’t actually taking financial accountability for achieving that outcome. It invites the question: why not? Is Best Doctors not confident enough in their product to do so? Put your money where your mouth is.

The entire dialogue summary is interesting to read and the end result of Best Doctors keeping its contract with SFHSS, albeit at a slightly lower rate, hits on a few other themes from this series:

  1. The importance of the consultant. Check out the integral nature of Aon, SFHSS’s benefits consultant, in this dialogue. Aon is providing the reporting on the program. The Board is asking Aon to negotiate the rate with Best Doctors. Aon is making the recommendation to the Board to approve at a lower rate. If Best Doctors didn’t have Aon’s support in this process, it’s easy to imagine how this relationship could have fallen apart.

  1. The importance of stories. If you look through the support for the proposal, you see repeatedly Commissioners expressing support due to positive member feedback in the program. 

Without the stories of real, positive member feedback and the consultant relationship, it seems likely that Best Doctors may have lost the deal altogether.

Make your product easy to understand and communicate to others

Your ability to have your audience quickly grasp the concept is necessary to get past the first meeting and becomes increasingly important as the internal socialization happens with other stakeholders and decision making bodies at the prospect. 

The simpler you make it for the benefits team/brokers to carry forward your value prop to other stakeholders, the easier you make the change management process. Benefits changes are highly personal to each individual and employees are sensitive to those changes. Each stakeholder is a potential consumer of the benefits so the personal sensitivity in the change management exercise is heightened. 

Executives can easily move away from an ROI based decision making process in benefits. I’ve heard “I don’t think I’d use this benefit” or “I don’t understand this and therefore no one else will.” This is why it’s so important to simplify and make personal the problem and your solution, so the different audiences can emotionally connect with the product as a health user of the benefit.

Some examples of things you can do that can help buyers or stakeholders:

  • Build a 1-3 page executive deck integrating stories and data. 

  • Have a rinse and repeat focus group playbook to prove out that employees will understand and would like the product.

  • Provide a digital solution to make it easier and faster to understand on mobile devices. 

  • Give your brokers bite sized info and updates to share with clients. 

This is really all about asking what other audiences do your key buyers interface with and how will those audiences best absorb the needed info – a stakeholder & change management exercise.  Then get ahead of it to help your buyers or stakeholders in the process.

While BestDoctors served as an example of what not to do in terms of aligning incentives with employers, they have done a nice job of making their product easy to understand and communicate via a digital solution. Check out the site they created for their partner, Aon, which provides a good example of creating easy to use digital documents, including overview decks, case studies, as well as employee engagement collateral. The site is a bit dated at this point, but the general takeaway remains.

Make your product easy to implement 

Implementation can include a lot of things that are always top of mind in the overall cost benefit analysis for an employer - especially large market employers where the process is less standardized. Some of these include:

  • Legal Review

  • Contracting

  • Security Audits

  • Product customizations

  • Data file feed testings

  • Integrations with existing HRIS (Human Resources Information Systems)

  • Integrations with other 3rd party vendors 

  • Marketing

  • Etc. 

But at its most basic level, an employer wants to know: how much work are you able to shoulder to make this as easy as possible? The easier you are to implement and the stories (or referrals) you can provide to create comfort around that, make saying “yes” much easier. But there is a lot to that and “integration” is a complex word in health benefits. It might mean simply sending an enrollment file back and forth or it might mean customizing SSO so that each vendor is integrated in the benefits front door platform the employer has in place.

Most large employers have an expectation that vendors will customize to work within the employer’s workflows, so be ready for those asks and try to identify them early. Smaller companies are typically more accustomed to standardized products and processes. However, they want to know the marketing collateral, the customer service, and the enrollment setup will be easy. Brokers and consultants frequently will have these same questions because they do a lot of this work for the employers so being on the same page with them is important.

Oftentimes the nitty gritty of “implementation” doesn’t happen until the contracting phase, after the sale is complete (verbally). However, you want to make sure you hit on the hot button topics early in the process so you don’t find any show stoppers after you have invested a lot of resources into implementation. It is also very helpful to set expectations on both sides about the implication of customizations should you go down that path.


That concludes our section on how to maximize win rate by taking an empathetic approach to all of your interactions with employers. By taking an empathetic approach, it maximizes the likelihood that your solution makes your employers and employees lives easier. That, in turn, will make your organization more successful.

Now that we’ve covered off on the numerator variables it is time to shift to the denominator. Let’s look at the sales cycle, which will help frame up the sequencing of the variables in the numerator.

On to the Sales Cycle article.

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