
From 2,500 to 30,000+ Users: Building EnrollHere's Growth Engine
Not a batch of videos. An integrated content, authority, and sales-enablement system that helped a Medicare-technology company sell faster, convert more, and earn the kind of proof sophisticated buyers actually trust.

Authority Content That Opens the Right Conversations
EnrollHere CEO Tyler Rees on the system of record for insurance distribution. Produced as a credibility asset the sales team uses to open conversations with agencies, field marketing organizations, and carriers.
Sophisticated Products Cannot Be Sold With Advertising Alone
EnrollHere operates where Medicare, insurance technology, brokers, field marketing organizations, carriers, and compliance all collide. In a market this technical, the job is to make a complicated idea feel simple and let buyers arrive at confidence on their own terms.

One Integrated Engine, Not a Stack of Vendors
We built the pieces to reinforce each other. One production should not create one deliverable. It should create an ecosystem of useful assets.
Brand Positioning
Clarify what EnrollHere is and who it is for, so every asset says the same thing.
Executive Thought Leadership
Put the CEO's point of view on camera to build category authority.
Customer-Led Proof
Let real operators describe the problem, the change, and the business result.
Long and Short-Form Video
One shoot feeds a documentary-grade feature and dozens of platform-native cuts.
YouTube and Social Distribution
Educational YouTube plus native LinkedIn and Instagram to compound reach.
Sales Enablement
Clips a rep can drop into a live deal to shorten the path to yes.
Search and Answer-Engine SEO
Crawlable transcripts and pages so the story is found by people and AI.
AI-Assisted Production
Agentic workflows research, organize, and repurpose so throughput scales.
How One Story Becomes an Entire Library of Proof
This is the Whisenhunt Media differentiator. A single customer production cascades into assets that serve marketing, sales, and search for months.
Assets Built to Do a Job, Not to Fill a Gallery
The System of Record
EnrollHere CEO Tyler Rees frames the category and the vision. Authority content that positions EnrollHere as the operating system for insurance distribution and gives sales a credibility asset.
Transcript
EnrollHere is a system of record. Prior to EnrollHere, we distributed life and health products every which way, from field to call centers, seminars, retail locations. We pretty much met the consumer where they were, grew it, scaled it, sold it. In August of 22, we looked at the insurance space and we said, hey, how could we be helpful? Where could we create differentiation? And we said the area of focus is technology and data. Traditionally within insurance, technology is super siloed. So you have call tracking and call routing, contact center as a solution products, AI tools for compliance scoring, quoting and enrollment engines, commissions, policy management. They're all fragmented. We just felt blind. We had 100 call centers that were working for us. They were on 20 different call center platforms. From a compliance and sales overview perspective, we just had no oversight, no insight to be able to really optimize and grow. We knew we were hitting a home run, but we didn't know where we were hitting singles and doubles versus striking out. When we started EnrollHere, we said, hey, from the time the consumer first says they're interested through the lifecycle of the policy, every interaction, every data set we're going to capture, we're going to analyze it, ingest it, structure it, and then display it, and ultimately allow our agency partners and agents and insurance carriers to optimize, scale, and grow. And that's what we've done. We really are one of a kind. Most recently we've launched EnrollHere Complete, which is an end-to-end solution. We had a partner last month consolidate seven solutions into one. When you think about being able to deliver a solution where someone can come and they can just have one login and they can live and breathe and do everything they need to, there's just not a competitor out there today. We built AI solutions that transcribe and record every call, score it based on CMS standards. And when we first rolled out the compliance scoring platform internally, the average compliance score on the platform was 40%. Through trial and error, through pushing it out to partners, through agents taking positive feedback, doing more training, working together with their agents, we can proudly say now that that number stands at 88%. So just significant improvement from a compliance perspective. With technology where it is today, every enrollment should be recorded, scored, and measured. And we should make sure that the seniors are getting treated and getting enrolled in the plans that make most sense for them, and we should be holding everyone accountable. For me, it starts with the senior. Seniors are our most vulnerable population. I think sometimes people lose touch on what is the most important component to what we do, and it's to serve the senior, to make sure when they get to later stages of life, they're focused on health and wealth. My mission is to create an environment and create a platform that allows us to optimize that experience and make sure that agents are behaving the right way, seniors aren't being misled by noncompliant and aggressive marketing, they're being put into plans that actually have benefits that they want, and ultimately that they're utilizing those benefits. If we focus on the senior, everything else will fall into line. I know that agencies and people that choose to partner with EnrollHere are going to have success and are going to win, and we're going to do everything in our power to make sure we deliver, and we help them achieve the goals that they set out to accomplish. And that's my pledge, and that's my promise to any customer. I will do everything I can, and my team will work tirelessly to stay at the forefront of technology, be pioneers, and lead us into different categories and creating new solutions. That commitment I take very seriously. EnrollHere is the system of record for the insurance industry, where agents, agencies, and insurance carriers can come to optimize, scale, and grow their business.
AmeriLife Customer Story
A named customer, AmeriLife, describes a concrete operational result. Evidence, not advertising: a peer telling other operators what changed and what it was worth.
Transcript
My name is Bill DeCourcy. I'm the chief lead generation officer at AmeriLife. EnrollHere is one of our key partners. They power LeadSTAR, a proprietary brokerage lead product for agents under contract with AmeriLife. They've absolutely revolutionized the LeadSTAR business, and they're starting to really come into our call center space and make dramatic changes there. Our cost per sale has dropped 35% since the implementation of EnrollHere. Our Medicare agents using LeadSTAR can now expect CPAs in the 150 to $160 range, which is profitable all day long. It absolutely does pay for itself. And it's not just the technology, it's the team. It's the expertise. It's the advice. It's the partnership. EnrollHere has been a critical partner for us to be able to scale. We were previously constrained by small development teams, teams that needed to learn the business before they could really operate in the business. EnrollHere has none of that. They bring proven operators to the table. I've worked with a lot of these partners, and what you have to do is you have to educate them about what the business is about before they can even start to return results. That's not the case with EnrollHere. They know the business, they come in, they deliver on day one. Every executive wants to make decisions based on data. The problem is generally two things: you don't have the data, or you have the data and you don't trust it. And EnrollHere eliminates those problems. All the data is at our fingertips and it's on a dashboard. I feel like I have total control now. Nothing is obscure to me anymore because of the data that's provided through the system. You can clearly see that the system was built on a data-first approach, because everything is surfaced and, more importantly, you're able to filter everything by what's important, build your own view, manage your business effectively. It's absolutely been a game changer for us. EnrollHere really looks to protect its partners. And one of the ways they do that is by emphasizing compliance. They've worked with us on AI-powered compliance so we can give better feedback to our agents, as well as working with the lead vendors that we bring in to make sure that they're meeting all of our compliance standards, so that we catch the trouble before we get in trouble. The biggest weight that's been taken off our shoulders since we implemented EnrollHere has been the compliance side of things. It's an extraordinarily risky area of operating in the Medicare space, and EnrollHere has all types of trust layers built through the product that allow us to say to our carrier partners and to our business partners, we're doing an exemplary job in this area. When one day turned into one week, and then one week turned into one month, and one month turned into one entire ADP, I absolutely marveled at the results. We were able to go back to our leadership, our board of directors, and say, this is what we were able to accomplish by partnering with EnrollHere. If you're on the fence about EnrollHere, it's probably because of one or two reasons. A, you think it's too good to be true. Trust me, it's not. And B, you might think that it's not something you can afford. Personally, I don't think people in this space can afford to be without it.
Customer Stories, Distributed
Real customers, cut for the platform and posted where their peers already are. Each clip links back to the live post.
More Than a Platform
Software is just a tool, but a partnership is an asset. Conner Van Duyn discusses why the relationship with the EnrollHere team is just as valuable as the code itself.
#Partnership #BusinessGrowth #CustomerSuccess #MedicareSales #EnrollHere
View original on InstagramTranscript
I do feel like it's more of a partnership, having the relationship with this team. They're so receptive to feedback. This is a team that when you have ideas or insights and you share that with them, it's something that not only is taken seriously, but things are done with it.
The “Piecemeal” Problem
Why manage five different vendors when you can have one? Megan Guido explains why “piecemealing” your tech stack is a barrier to scaling and how a unified ecosystem makes the transition to growth simple.
#InsurTech #AgencyOperations #MedicareSales #BusinessEfficiency #EnrollHere
View original on InstagramTranscript
Making the decision was quite simple, because I feel like they provide such a comprehensive scope of work that there's not really too many other options to choose from. If you're looking to comprehensively scale your business, start a cold call center, even if you want to have exclusively contracted agents, work in the field, they provide so much detail all in one place. You can kind of piecemeal your workflow with a lead distributor and a commissions platform and everything like that, but EnrollHere encapsulates everything all into one. So I wouldn't say that there's necessarily too many different competitors that we were even contemplating.
Scaling for the Family Business
Scaling isn't just about numbers, it's about the people. Austin Levin talks about running a family-owned business and how EnrollHere provided the tools to scale while protecting the livelihoods of his agents and their families.
#FamilyBusiness #Entrepreneurship #MedicareBroker #AgencyCulture #Success
View original on LinkedInTranscript
As an agency owner, having the tools to be able to control my business and operate my business from anywhere: not only is stress decreased, but it's also an opportunity once again to scale. We're family in business. This has helped immensely and tremendously, because it's helped everybody sell more Medicare and retain more clients.

Evidence Beats Advertising in Sophisticated B2B
In technical sales, people trust peers who have lived the same operational problems. Instead of asserting that the platform works, the content lets customers demonstrate it in their own words.
Advertising says
“EnrollHere works.”
Evidence says
“Here is the problem we had. Here is what changed. Here is what it meant for our business.”

What the Program Helped Support
Reported during the engagement period. These results reflect the broader marketing and sales ecosystem, of which the content program was one contributing part.
Average Sales Cycle
28 days7 days
Lead Conversion
5%22%
Presentation Win Rate
50%76%
Customer Referrals / wk
1-310-15
Avg Pipeline Deal Size
$25K$154K
Qualified Database
50500+

00+
EnrollHere platform users during the growth period
This growth coincided with the broader marketing, product, and sales ecosystem operating together.

Outside Conviction in the Trajectory
This momentum coincided with continued organizational expansion and a strategic investment from Aquiline, a global private-investment firm specializing in financial services and technology that managed approximately $12 billion in assets as of December 31, 2025.
Announced in April 2026, the investment is intended to advance EnrollHere's AI platform for Medicare Advantage distribution. We frame this as outside validation of EnrollHere's long-term vision and technology, not as an outcome Whisenhunt Media caused.
Read the Aquiline announcement$12B+
Aquiline assets under management
as of Dec 31, 2025

Human Judgment Decides What Gets Multiplied
“AI is definitely a force multiplier. It is a leveler of the playing field, if you are using it. There still needs to be the human element, the tastemaker putting their thumbprint on it. If you do not, you get slop back.”
Agentic workflows let a small team operate like a large one. AI helps us research faster, organize information, analyze content, spot repurposing opportunities, coordinate campaigns, and maintain a larger content system with real search visibility.
What it does not replace is creative direction, editorial judgment, storytelling, production quality, and strategy. For EnrollHere, that combination is how 15 medium-form videos plus roughly six months of daily short-form were produced in about one month, work that would traditionally take two to three.
A System Where Every Stage Reinforces the Next
Businesses do not need another disconnected vendor producing isolated marketing assets. They need an integrated system where each stage compounds the one before it.

Build Your Growth Engine
If your company already has a great product, strong customers, and a story worth telling, Whisenhunt Media can help turn those assets into a marketing system designed to compound.
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