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Employee Benefits Professionals: 5 Digital Tips to Prospect & Sell PART 1

Sep 01, 2020

How are your digital prospecting and selling chops? We’re now many months into working remotely – and many employee benefits professionals are struggling to figure out how to serve clients in this environment. 

It seems we’ll be working this way well into 2021, so it’s time to rethink how we approach prospecting, selling and retaining clients – in a digital world. 

At freshbenies, we have experience with this because we built our company remotely for a decade. Our core communications were via virtual meetings and digital marketing, paired with occasional local meetings and training. Did it work? Well, starting from zero, we’ve recruited 1,000+ brokers, helped them sell 2,000+ employer groups, and supported 100,000+ member households.

And we’ve met some digital prospecting and selling experts from our industry along the way, so we brought them together for an interactive session to share their secrets. This faculty included…

We also pulled tips from employee benefits professionals we interviewed for our series, “Brokers in Cars Getting Coffee”…

Click below to watch a recording of this 30-minute fast-paced session...

Below are session notes for the first two tips we shared. Each tip includes a few tricks and additional resources. Part 2 of this article will highlight the other 3 tips.


If you don’t know EXACTLY who your prime client is, you’ll spin your wheels on any marketing efforts. 

TRICK 1: Define your audience

Heidi Rasmussen, Co-Founder & COO at freshbenies, says the biggest mistake she sees as a marketer is jumping immediately to tactical plans like, “Should I be on Facebook? Should I send email newsletters? Should I start a blog?” and so on. 

Rather, start with strategy - define your client and be crystal clear about who your client is. Ask yourself, “Who is in the bullseye of my dartboard?” Of course, you’ll have other audiences that are also important – the outer rings – but you have to be very specific about your prime client.

Jeremey Mahoney


A perfect example is Jeremy who said, “We target engineers and architects.” If I’d had a further conversation with him, I’m sure he would have defined it even tighter. For example, “CFOs and benefits decision-makers at engineering & architecture firms with 100-3,000 employees in the state of Texas.” 

As you build your brand and messaging, you keep that prime client in mind – because it’s imperative that you build your brand for them. It’s not all about you. It’s about them and how you help them. All your messaging should focus on this. And you can't do that if you haven't really solidified who your prime client is.

Below are two articles from Heidi that go into this further:
Part 1: Branding Your Agency
Part 2: Building Your Agency Brand

Trick 2: Be Memorable

There’s a sea of brokers, insurance carriers, products, plans, and advice out there. So, think about what makes you different. When your prospects look you up online, what do they see? How do you stand out? Before the pandemic, you might have argued that your clients don’t look you up online. Maybe you believed your personality shines when you’re in person, and that your digital persona doesn’t matter. It’s time to take a new view of how you stand out.

For example, when we built freshbenies we knew we were an affordable cost-containment tool competing for attention amongst a slew of healthcare brands that all looked the same (the “BUCAHs”). We chose to make ourselves memorable with a unique name, bold colors, humor, a casual ‘voice’ and a professionalism that drove the highest outcomes. This attempt to be memorable has worked very well for us. 

To be memorable, you must identify and use your strengths. And then, convert to digital what made you memorable in-person. Sharon Tiger advises, “Let your personality shine. People want to do business with people.”

Are you an employee inside a large agency who thinks you aren’t allowed to have a digital presence because the company website doesn’t even list you? It’s a new day. You’re more than your company, you own your own personal brand. You have to find ways to make your virtual presence match your in-person presence. It’s time to learn how to show your authentic personality.  

Adam Compton shared a quick LinkedIn tip for being memorable on a connection’s birthday: “Avoid just using the 'Happy Birthday' note that everyone sends. I use the app ‘Smash Up' to send a personalized video with names. I sent one to a former client that moved to a different company: it had Donny Osmond singing happy birthday to her. It worked. I almost always get a response on those personalized videos.”

Make it impossible for your key prospect to forget you.

Trick 3: Embrace LinkedIn

If your main prospects are employers, it’s time to embrace LinkedIn. This social platform is today’s Yellow Pages, Rolodex, town crier and resume – all rolled into one. Personally, I look up everyone’s profile before I have a phone-call with them. Does your online profile paint an accurate picture of you? If not, fix it. Today. 

For some basics, start with this: 20 Steps to a Better LinkedIn Profile in 2020

When COVID hit, I had a tough time getting in touch with people. Emails and phone calls were going unanswered. But I noticed that some of those same people would respond to me on LinkedIn. It was a backchannel that became even more active as time moved forward. Now, let me be clear, I wasn’t sending long direct pitches like the ones I receive from strangers every day (and then delete). Here are three tips that have worked for me: 

  1. Interact with a prospect’s posts on a regular basis. It’s one thing to “like,” but get used to commenting, too. Express agreement, or sensible (non-aggressive) alternative opinions or disagreement. These are breadcrumbs that show you have ideas and can express them. Some people look to these things to check you out. 
  2. If the prospect is a total stranger, comment on two or three things they’ve posted. I promise they’ll know who you are when you message them.
  3. After doing points #1 and #2, when you message a prospect, work it like you’re texting or small-talking. Refer to their posts, tell quickly how the pandemic is impacting you right now and ask a specific question about how it’s impacting them. Be engaging – and use humor and GIFs available in Messenger. After a few back-and-forth messages, you might ask about setting up a call to help them with something they said. Let your personality come through so they know you’re not an “auto-message” they receive from so many others. 

Sharon Tiger

This year Wendy Keneipp schooled me on the types of posts LinkedIn algorithms like, and therefore result in more exposure. My main activity was sharing articles or someone else’s post, along with a little of my own perspective. I noticed they weren’t getting as much play as they used to. The formulas give way more play to original content. Wendy found that if you post a link that directs users to another website, you shouldn’t put it in your main post. Instead, add it in the first comment under your post. If you add a photo, that’s even better. Add a video, and that’s the best – even a simple short clip from your phone. 

If you’re already a LinkedIn whiz, try some paid advertising. If you have a LinkedIn Company Page, you can choose from Matched Audiences, LinkedIn Live, and Lead-Gen forms. Click here for a great recap article on this topic.


Especially in this environment, you’ve got to be in front of your prospects and clients consistently with helpful content and forward-thinking ideas. Since you can’t do it in-person, it’s time to shift to using your digital presence to show that you’re an authority.  

What is content? Articles, videos, infographics, white papers, case studies.

You’re probably thinking, “I can’t possibly create all of that!” The good news is, you don’t have to. But you do have to get good at curating great content for your audience – with your perspective.

Trick 1: Use Your Vendors

Most of your vendors create awesome content you can grab and use. 

At freshbenies, we’ve been doing this for eight years – and have produced a LOT of content to help our brokers and employers over the years. So this year we reorganized it all into a new page called “Your Ultimate Guide to Employee Benefits Consumerism Tools.

Ultimate Guide to Consumerism Tools

By doing this, we simplified your search and organized dozens of content pieces into eight categories on a “Hub Page.” Watch for other pages like this because other vendors are doing them and they’ll be a treasure trove for you.

Once you find good sources of content, your job is to curate the info to suit your audience. But you need to MAKE IT YOUR OWN. A content piece is a GREAT way to start a conversation with your clients and prospects. Here are a few real-life examples…

  • Send a video prior to your next client meeting as a pre-watch to discuss.
  • Present a case study to spark a conversation in your mid-year review.
  • Share an article in a monthly newsletter to prospects or clients.
  • Use a white paper as an education piece with all your clients. Say, “This is becoming more of an issue with some of my other clients. How is your team handling this?”
  • Post an infographic on LinkedIn to show you’re a thought leader and get a conversation going. For example, go to the freshbenies Ultimate Guide. Click on Section 4 – How do I win with Telehealth? Find the Infographic on Behavioral Telehealth and you’ll see that Page 1 shows nine statistics. You could take each stat and create a post about it. Just quote the stat, attach the image, write a couple more sentences about it and ask, “Is this an issue with your employees during the pandemic?” 

Trick 2: Create Various Types of Content

We all have different strengths. Work yours. And experiment with some new things, too.

Your strengths

Many of you know David C Smith. If so, it’s probably because you’ve been in one of his many training classes across the country. Creating and teaching classes is his “content of choice.”

As for Kevin Trokey, one of the most likely ways you’ve learned about his coaching and teaching is by reading one of his articles or blogs. That’s one form of content he’s been consistent with for years.

Then there’s Bret Brummitt, who was the first broker I saw pick up a video camera and a microphone. He started recording vendors, clients and even himself. He posts education, case studies, testimonials and more. It’s a perfect type of content to showcase his dry sense of humor and his philosophical view of the world.   

Nancy Giacolone started dabbling with LinkedIn posts, and she stretched herself to share a weekly video she calls “Two Minute Tuesday.” She finds something in the news, from a carrier, or from a client in the week leading up to it that she can speak to. Once you start looking, she says, “Life is full of content!” Today, she’s earned a number of clients who first learned about her online. 

Nancy Giacolone

Sharon recommends the book “Blueprints for a SaaS Sales Business” for those who want to delve into this more. She quoted them as claiming that “today’s rainmaker is a content creator.”

Trick 3: Re-Use Content Everywhere

Another trick Heidi taught me is to re-use, re-cycle and re-post your content across all channels. If you post something to the digital universe one time, it doesn’t mean everybody saw it. It’s appropriate to push it out multiple times.

For example, in April we launched this broker interview video series called “Brokers in Cars Getting Coffee.” 

  • We post each episode to LinkedIn. See an example here. Meaning, we post it to the freshbenies company page. And Heidi, each of the members of our sales team, and I post it to our personal pages. 
  • We post it to Twitter, via the freshbenies account.
  • We share it in our email newsletter.
  • Next, I write an article that posts a copy of the video, summarizes the lessons, profiles more background on the interviewee, and tells some of the great advice that was left of the Cutting Room Floor. See an example here. We post that on our blog. And then push that out again on LinkedIn. And in the newsletter.
  • Then, we use the lessons from the interviews in classes we teach. Like this one. Which we’ll post in a blog. Like this one. And share it across those other channels.

The goal of all of these channels is to increase viewership, social followers, email audience, class attendees, and then – clients.

You don’t have to do all this with your content. But take the lesson to recycle whatever content you curate and modify it for the channels you use. 

Click here to read part two of this series with tips #3, 4 and 5. Please email me at with your questions, stories, and ideas of what’s working this year on building your own digital presence. 


Reid has a passion for helping brokers & employers strategize fresh approaches to benefit plans that contain costs and increase access to care - helping employers & employees control their healthcare dime, time, and peace of mind. He writes & speaks around the country and is the Co-Founder & CEO of freshbenies.

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Tanya Boyd
President of Tanya Boyd & Associates

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