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Contents

  1. 01Executive Thought Leadership
  2. 02The Challenge
  3. 03The System
  4. 04The Content Engine
  5. 05The Work
  6. 06Business Outcomes
  7. 07Platform Growth
  8. 08External Validation
Build Your Growth Engine
A hand tees up a golf ball branded with the EnrollHere System of Record logo
Flagship Case Study · EnrollHere · Medicare Technology

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.

287
day sales cycle
5%22%
lead conversion
2.5K30K+
platform users
Build Your Growth Engine See the Work
EnrollHere leader speaking at an industry event
Executive Thought Leadership

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.

The Challenge

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.

Education
Trust
Independent proof
Customer stories
Clear positioning
Executive authority
Repeated exposure
Complexity made simple
Strategy session, mapping the plan on a whiteboard
The System

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.

The Content Engine

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.

01Customer interview and production
02Long-form customer story
03YouTube authority feature
04Short-form vertical cuts
05LinkedIn clips
06Instagram Reels
07Quote and proof graphics
08Sales-enablement clips
09Website proof
10Searchable transcript and SEO
The Work

Assets Built to Do a Job, Not to Fill a Gallery

Executive Thought Leadership

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.

Customer Proof

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.

InstagramConner Van Duyn

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 Instagram
Transcript

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.

InstagramMegan Guido

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 Instagram
Transcript

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.

LinkedInAustin Levin

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 LinkedIn
Transcript

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.

Operators and peers talking at an EnrollHere event
Customer-Led Marketing

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.”

A golf ball at the edge of the cup
Business Outcomes

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+

Aerial view of the Pinehurst golf course at sunrise
Platform Growth

00+

EnrollHere platform users during the growth period

This growth coincided with the broader marketing, product, and sales ecosystem operating together.

Las Vegas skyline at dusk
External Validation

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

The team working through the plan, whiteboard behind
AI as a Force Multiplier

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.”

Ben Whisenhunt· Founder, Whisenhunt Media

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.

What This Proves

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.

Strategy→
Story→
Production→
Distribution→
Search→
Sales→
Measurement
The EnrollHere community gathered at the event

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.

Let's Build Yours Get a Free Analysis

Explore more: portfolio · Cardenas Law Group case study · contact

Reference & Video Summaries

Full text for accessibility, search indexing, and AI reference.

About EnrollHere

EnrollHere is an AI-powered system of record for insurance distribution, built for the Medicare Advantage market. Its EnrollHere Complete platform unifies marketing, call-center operations, agent performance, compliance monitoring, policy lifecycle, commissions, and payments in one place. Founded in 2024 and based in North Carolina.

Learn more at enrollhere.com.

About the EnrollHere engagement

EnrollHere is an AI-powered platform for Medicare Advantage insurance distribution, founded in 2024 and based in North Carolina, whose EnrollHere Complete product unifies marketing, call-center operations, agent performance, compliance monitoring, policy lifecycle, commissions, and payments into one system of record. Whisenhunt Media built an integrated content, authority, and sales-enablement ecosystem around the company: executive thought leadership, customer-led proof, long-form and short-form video, YouTube and LinkedIn and Instagram distribution, and AI-assisted production. As one example of throughput, the program produced 15 medium-form videos plus roughly six months of daily short-form content in about one month, work that would traditionally take two to three months.

Video summary: The System of Record (Tyler Rees, EnrollHere CEO)

Executive thought-leadership video in which EnrollHere CEO Tyler Rees frames insurance distribution around a single system of record. Its business function is authority: it positions EnrollHere as the operating system for insurance distribution and gives the sales team a credibility asset to open conversations with agencies, field marketing organizations, and carriers.

Full 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.

Video summary: AmeriLife customer story (Bill DeCourcy)

Customer-proof video featuring AmeriLife, in which the customer describes reducing Medicare cost per acquisition by 35 percent using EnrollHere. Its business function is evidence: a named peer telling other operators what changed and what it was worth, which is more persuasive in technical B2B sales than product advertising.

Full 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 story videos (social distribution)

Short-form customer testimonials cut for each platform. Verbatim post copy, with links to the live posts.

  • Scaling for the Family Business, Austin Levin (LinkedIn)

    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 post)

    Transcript: 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.

  • More Than a Platform, Conner Van Duyn (Instagram)

    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 reel)

    Transcript: 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, Megan Guido (Instagram)

    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 reel)

    Transcript: 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.

Reported business outcomes (during the engagement period)

These results reflect the broader marketing and sales ecosystem, of which the content program was one contributing part, and are not attributed to any single cause.

  • Average new-client sales cycle: approximately 28 days to 7 days.
  • Lead conversion: approximately 5 percent to 22 percent.
  • Sales-presentation win rate: approximately 50 percent to 76 percent.
  • Weekly customer referrals: approximately 1 to 3, up to 10 to 15.
  • Average pipeline deal size: approximately $25,000 to $154,000.
  • Qualified marketing database: approximately 50 to more than 500 leads.
  • EnrollHere platform users: approximately 2,500 to more than 30,000.

External validation: Aquiline investment

In April 2026, EnrollHere announced 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, to advance its AI platform for Medicare Advantage distribution. This is presented as outside validation of EnrollHere's trajectory and long-term opportunity, not as an outcome caused by Whisenhunt Media.

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