Enrollment Specialists: Gatekeepers of The Art of Applying® Community

Written by Dylan DaCosta, Head of Enrollment for The Art of Applying®

This has been a big week for me. After 15 months of working as an Enrollment Specialist (the role was formerly referred to as a Breakthrough Coach), I’m very honoured (I’m Canadian so I spell it the Canadian way) to have just been promoted to the Head of Enrollment here at The Art of Applying®.

As Head of Enrollment, my job comes with many new responsibilities, including the hiring and training of Enrollment Specialists as well as mentoring and managing our existing Enrollment Specialists. As the greatest Enrollment Specialist of all time (modesty is not one of my qualities), I know a thing or two about what makes somebody successful in the role. I decided to write about that today since every single person who ends up working with us as a client must first have a call with one of our Enrollment Specialists and be invited to work with The Art of Applying®.

What An Enrollment Specialist Does

First, it’s important to understand exactly what an Enrollment Specialist actually does. Put simply, our Enrollment Specialists act as the front line of the business: they speak to potential clients and, if there is a strong fit between the applicant’s problems and our solution, help them get started on working on their applications with our team. From email correspondence before the call, to an in-depth 90-minute personal (and sometimes emotional) discussion, to celebrating when applicants hear back from their schools, the Enrollment Specialists have the privilege of sharing in the success of our clients nearly every step of the way.

The job of an Enrollment Specialist is incredibly simple, while being extremely challenging. At The Art of Applying®, we are selective about who we work with because we want to focus our resources on the people we can most help and will most enjoying working with. Thus, rather than simply letting people purchase services directly from our website, every single person who eventually becomes a client first has a call with our team.

During the call, the applicant and the Enrollment Specialist will talk about their goals, dreams, challenges and fears. After hearing about all of those things, the Enrollment Specialist will make an honest assessment of whether we can help or not. If The Art of Applying® can help solve the problems that the applicant has, the Enrollment Specialist will invite the person to work with us on their applications.

This process is easier said than done, though, as humans are often scared of making transformative change or investing in themselves when compelling so-called shortcuts or cheaper options exist. Often our Specialists take time to ease a multitude of applicants’ fears (“Will this actually work for me?” is a big one), listen to applicants discuss extremely personal challenges, and powerfully hold space to encourage people to seize their dreams.

Dylan in Kiev, Ukraine for the 2018 Champions League Final between Liverpool F.C. and Real Madrid C.F.

What It Takes To Be A Successful Enrollment Specialist

The job, in essence, is easy, but it requires some key ingredients in order for someone to be the right fit for the role. First and foremost, it requires incredible resilience. While we aren’t run of the mill “salespeople,” we are still in the position of offering Ivy League hopefuls the chance to work with us. It’s possible that some of those people will decline the offer, whether it be due to financial constraints, uncertainty over the timing of their applications, or some other factor holding them back from taking the leap.

On the other hand, the Specialists have to have the integrity and honesty to tell potential clients “no” and not invite the person to work with us when telling the applicant no is the right thing to do. For example, some people don’t embody the personal qualities we’re looking for in a successful applicant (specifically, we require that our clients to be coachable, decisive and resourceful) or just simply aren’t a fit for us and our team.

To be a successful Enrollment Specialist, you have to be capable of saying and hearing the word “no”—sometimes all day long. Having the mental fortitude to cope with frequently hearing no in its many forms (“not yet,” “maybe,” and “I’ll think about it and get back to you” are all different ways we hear no.) as well as witness the emotions of other human beings while maintaining your own internal balance is integral to being able to handle the job. Someone who has poor boundaries, expects the job to be easy, or doesn’t know how to shake off rejection will not last long in this role.


The second quality an Enrollment Specialist needs is a well-tuned mindset. With anything in life, mindset is extremely important. The people with clarity of their goals, and the commitment to achieve them, are always the ones who get the things they want. An Enrollment Specialist has to maintain a positive, future-oriented mindset. Human beings are attracted to others who are heading in the same direction, and in order to bring the best clients (the ones with the drive, desire and passion that we are looking for) to The Art of Applying® community, we need our Enrollment Specialists to be a mirror of those desired traits.

In order to cultivate a rock solid mindset, our Specialists read (or listen to) self-development books (a recent one was You Are a Badass), listen to podcasts (Your Wish is Your Command is one I like), create detailed personalized mission statements, loudly chant affirmations in the mirror (maybe I’m just speaking for myself on that one) or do whatever else it takes to keep their minds sharp and their energy positive. As Head of Enrollment, I must make sure I am consistently working on my mindset, and it is also my job to keep the Enrollment Specialists accountable to maintaining a strong mindset.


But above all else, an Enrollment Specialist needs to have integrity. Again, we are not salespeople in the strictest sense of the word. We are not trying to sell something that someone else may or may not want or need. We are here to offer a life-changing opportunity to the people who are the right fit for working with us—and nothing else. We do not convince, beg, plead or desperately need any one individual to work with us, because working with the right people is more important to us than working with the most people.

Because of this, an Enrollment Specialist will only succeed if they have a high degree of integrity. A successful Enrollment Specialist will occasionally need to be blunt, painfully honest and willing to tell people a hard truth that they need to hear. A hard truth could be telling someone we can’t help them or that they’ve already made a significant mistake in their application process. One story that comes to mind is when I had to turn away someone who had assumed they could apply to the joint MBA and MPP at Harvard in subsequent years—when you can only apply to the Harvard MBA/MPP joint degree in the same application year, thus disqualifying herself from being a joint degree applicant—all because she had received and followed erroneous advice.

Our Head of Enrollment enjoying some R & R in beautiful Muskoka, Ontario.

Sometimes, the job entails powerfully holding space to help a scared client figure out if working with us really is the right fit or not. Our Enrollment Specialists will not offer you something you don’t need, but neither will they quickly let you give up on your dreams or delude yourself into thinking everything is fine if you don’t get the help you need. Our Specialists need to embody integrity and consistently demonstrate the willingness to encourage the applicants who come to us for help to take the necessary steps to transform their lives.

For 15 months, I’ve lived and breathed The Art of Applying®. Transitioning from a career in the newsroom to serving as an Enrollment Specialist with The Art of Applying® was the best thing I’ve done in my entire career. Despite how much I love my job, I’m still human, and I’ve experienced the highs and lows that come with any role.  Early in my time with the company, I enrolled someone in our program on a three-hour long Breakthrough Call to accommodate her Spanish-speaking parents with a translator. I was delighted to have helped another person, and felt very proud at being able to include her parents in the discuss and come to a mutual understanding that The Art of Applying® was the best fit for their daughter’s application. Just a day later, though, that same client had a change of heart and requested a refund and the termination of their contract. It was heartbreaking for me to see her shift so quickly from excited about her future to being scared about the commitment.


However, helping some of the world’s most ambitious people claim their dreams is the most rewarding thing I can imagine myself doing. I get it to do it every day as I help The Art of Applying® grow as a business, and I get to do it every day as my team of Enrollment Specialists and I help people transition from being grad school hopefuls to Ivy League alumni.

And so that’s what I’ll be looking to hire for as our team continues to grow: the people with the positivity, resilience and integrity needed to attract the ideal people to work with us. It’s not an easy job, and at times it can be downright exhausting. But it’s one that is worth it. As a member of The Art of Applying® team, Enrollment Specialists have the chance to help the world’s future business owners, thought leaders and politicians by doing our jobs as best as we can. That’s an incredibly exciting thing to say.

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