Rich Hogan, CEO of Enrollsy, talks with us about enrollment’s critical nature in business success and how Enrollsy brings massive productivity gains to various workplaces.
Q. How long has Enrollsy been around, and how did it get started?
I incorporated Enrollsy as a Delaware C-Corp in 2017. However, the idea for Enrollsy started long before that. It was a combination of a few things in my personal life that brought the idea to fruition.

CEO of Enrollsy
First, I discovered through a series of challenging circumstances that I didn’t want to work for anyone else ever again. I wanted complete control over my career success or as much control as possible.
Second, I noticed that my wife kept complaining to me about the enrollment processes required for getting our kids into sports camps, preschool, music classes, and more. She described paper forms and long lines early in the morning to secure a beloved preschool teacher. Once the printer being out of ink stopped my wife from completing enrollment for swim lessons at the only convenient time during a hectic day. I realized that there was an opportunity to address some incredibly archaic processes within the enrollment space, so I jumped in.
Q. What did you do before Enrollsy?
Before Enrollsy, I helped procurement and risk management departments manage vendors, contractors, suppliers, and tenants. I worked with companies like Hilton Worldwide, CBRE, FedEx Ground, Radisson, and many others. Oddly enough, many challenges small and medium businesses face with enrollment are enterprise challenges, too, only at a grander scale.
Q. I don’t see the connection between the two? Tell me more about that.
Yeah, for sure. At Enrollsy, we consider an enrollee to be any entity with whom an organization has an ongoing relationship. The challenge comes down to collecting data from these entities in a clean, consistent manner that minimizes the workload by enabling enrollees to self-onboard. There’s also a challenge in management of this data and in managing the relationships using that data.
We start by making the data collection and organization easy. Instead of one, or a few people doing a massive amount of work, you distribute it out evenly among every enrollee or vendor. In many cases, you collect a fee as part of the process. Schools, of course, charge an enrollment fee and tuition. In contrast, enterprises might charge an annual fee to vendors (either directly or indirectly) to cover costs associated with enforcing contract compliance, among other things.
It doesn’t matter if the entity is the parent signing a financial agreement with a preschool, a construction contractor signing an MSA, or a commercial tenant signing a lease. It’s practically the same process, and in many instances, it’s a process filled with inefficiency traps and manual work.
Consider a parent enrolling their child in daycare or preschool. Many states have required forms with the same information on 3-4 different pages, which is a big waste of time and a horrible customer experience. In most cases, the parent has to complete the packet by hand and sign it in multiple places. Furthermore, let’s assume that an administrator at the preschool has to collect all these packets. Can they read the parent’s handwriting? Did the parent fill in every required field and sign where necessary? How does the administrator of the school get this data into their software? You can only imagine how much time is wasted for a school with 2,400 enrollments annually. And again, it’s not a good experience for the parents.
Now, let’s compare the enterprise. They sometimes have tens of thousands of vendor relationships. Depending on the work scope, vendors might get divided into different groupings that require unique information to be submitted. Furthermore, their work scope will determine what kind of an agreement or contract they need to sign. Work scope might also require the vendor to self-report their safety records and other data vital to risk analysis. Now, the large enterprises will say they have this under control, already use eSignatures, or have internal software they built to streamline this. But, time and time again, I found that receiving current, complete, and accurate vendor data was more challenging for them than almost anything else. Not to mention many of them didn’t know if they had an existing contract with a vendor or if the one they initially executed had expired or not. Uniformity in the enrollment processes becomes more challenging, not less challenging, as its size increases.
Can you see how similar these use-cases are when you break them down into the challenges and ignore the industry or company size?
Q. Yeah, I can see that. So, this is Enrollsy’s value proposition, to solve data entry and document management, including eSignatures?
It is, but we feel enrollment includes so much more.
There’s a whole bunch of activity that arises after successful enrollments happen. So, Enrollsy is about a lot more than just receiving data into a database. Retention and interaction concepts after enrollment are also vital to every business.
Q. Ok, I think I’m starting to see why Enrollsy isn’t just software for one specific type of company, but how did you get your first customer, and who was it?
You know, one day, with a little prodding from my wife, I got on the phone with John, my son’s preschool owner. I found out he owned and operated six centers in two states with about 2,400 enrollments annually. I described something different and showed him a couple of prototypes I had designed. John liked the idea, so without delay, I got started building Enrollsy.

Soon after, John became hesitant to switch from his current software provider. Years ago, a company called Child Care Manager sold John installed software. John had never used a cloud-based product for managing his business. I’m not sure if he got cold feet, but he backed out at some point in the process. I decided I still wanted to build the platform even if John didn’t move forward with us, but this was a blow early on.
A few months later, John found out that Child Care Manager was going to be acquired. He called one day to tell me that he preferred our approach to software over the new company. We officially launched with him in October of 2018. While we never had intentions of being strictly preschool or child care software, we realized you have to start somewhere. John gave us a great start by providing access to his already successful business and six Directors who were heavy users of our software from day one.
Q. That’s great. So your first customer was the preschool your son attended?
Yeah, that’s right. And we’ve been growing in the daycare and preschool vertical ever since.
Q. So, how many customers do you have right now, and what percentage are daycares and preschools versus other industries?
We are getting close to 100. That’s the first milestone. I think we’ll be there by the end of 2020 or Q1 of 2021. It’s interesting because we have found a nice little niche in the preschool and daycare space. Yet, we have about ten other industries we’re in, including camps, recreation/sports, art and music schools, professional schools, insurance, and a few others. While we plan to keep growing in these verticals, one of our goals for 2021 is to gain traction with medium to large enterprise clients. It simply takes time to get the software ready for the demands of enterprise users.
Q. Well, it sounds like you’re on your way. You mentioned earlier that enrollment is just the beginning. What other challenges does Enrollsy address?
Yeah, that’s a great question. If you think about what makes an enrollment-style relationship; it’s the fact that it’s ongoing. I mean, ten to twelve years ago, you could easily argue that e-commerce purchases were just one-time purchases. Amazon got things right in their strategy to turn every customer into someone with whom they have an ongoing relationship. How did they do this? They ask you to create an Amazon Prime account, or to enroll. They gather and store information about you, including your payment information and buying habits and they charge you an annual subscription fee. They email you and learn what your needs are. They develop products and services you can get more quickly from them than elsewhere because of this convenient account.
As all industries advance through technology adoption, every company will either turn into a commodity provider or they’ll develop deeper account-based relationships with their customers. In other words, they will enroll people in something, whether that’s a membership, a subscription, or something else.
So what we’re doing is building an account-based platform and a communication system with multiple channels, including:
- Texting
- In-app messaging
- Real-time notifications
- Emails
- Review collection
- And something we call activity timelines
None of these communication channels are new. But we’re passionate about what we’re doing and how we’re doing it, especially with activity timelines, which kind of is something new.
Q. Ok, I get that data intake and digital signatures work the same way for almost any company and that Enrollsy can do that. But, how is it possible that a preschool would need the same thing that a hotel or a co-working company needs in terms of communicating with its vendors or tenants?
Great question. Let me give you one example. With activity timelines, a daycare can create a custom activity allowing a caregiver to record something like an incident report or a diaper changing that a parent can see in real-time. In contrast, a co-working space can create an activity with a specific structure of questions necessary to gather the information required for a tenant to submit a maintenance request, including an image upload. The tenant can open the app 24/7 and post a maintenance request, and that request can get served up in a variety of ways to the property manager. That property manager can then share that maintenance request with an approved vendor. These timelines are extremely powerful because activities are customizable. Like many things in our app, the user can choose basic templates to get started quickly or customize from scratch.

Q. Very cool. And how much does Enrollsy cost?
We have a saying at Enrollsy that not everything affordable is easy. And not everything easy is affordable. Our lofty promise is to give you something that’s both. At this time, Enrollsy starts at just $25/mo for our Starter plan and goes up to $350/mo for our Enterprise plan. You can learn more about each plan at enrollsy.com/pricing.
Q. Rich, it’s been great chatting with you. I think you have a great product and I wish you the best of luck.
It’s been my pleasure. Thank you.
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