Enrollment Specialist (Educational Sales)

Note: We are currently actively hiring for Enrollment Specialists. We anticipate extending invitations to interview to promising candidates who submit their applications by Wednesday, July 11 at 11:59 pm ET (and the earlier the better).

If you miss the above deadline, we still encourage you to apply, because we hire for this position frequently and are always looking for great talent!

HIRING: Enrollment Specialists
(entry-level / early career educational sales job with no cold calling)

The Art of Applying changes peoples’ lives all over the world by helping them get into the best graduate schools in the world and get money to pay for it! Despite our love for prestige and the Ivy League, there are no fancy degrees required for the job we’re hiring for right now.

Joining The Art of Applying team as a Breakthrough Coach is an invitation to break out of boredom, overcome under-earning and reach your potential.

Within four months on the job, you can expect to earn $5000+ per month while working from home on a high-energy team helping amazing clients.

Look how happy your future teammates are!

Kyle, Dylan, and Tyler of The Art of Applying

Dylan (guy in the middle) is our Head of Enrollment. Just a year ago, Dylan was a small town reporter with no background in sales, and now he earns $5000-$12,000 per month working from home and helping make people’s dreams come true. When you join the team, Dylan will train you intensively and be there for you every day to answer your questions as you learn how to excel in your role. And don’t worry that you’re bothering him; Dylan gets paid to help you succeed, and the better you do at your job, the more money he gets paid!

Tyler (guy on the right) will be listening to the recordings of every single one of your calls and giving you feedback, helping you get better and better at being persuasive and effective on your calls. His feedback is candid but kind, so you’ll never be left in the dark wondering how you’re doing or how to get better.

Once you get someone enrolled in the program, Kyle (guy on the left) will have an onboarding call with your client, so that the person you just signed up knows how to find her way around her client portal and make the most of her time with us in the program.

Our clients are from all over the world and represent a myriad of backgrounds, cultures, and perspectives. We would love for you to considering joining our diverse team and advancing our mission of helping the world’s emerging leaders get into their dream schools.

About Our Founder & CEO

Hey there! I’m Kaneisha Grayson, and I’m the founder and CEO of The Art of Applying. I’m a 2006 graduate of Pomona College, and a 2010 graduate of Harvard Business School and Harvard Kennedy School.

I started The Art of Applying in my Harvard apartment. It’s grown from just me and a laptop in 2010 to a thriving business comprised of seven full-time employees and 15 contractors who live all over the world.

My team and I help high-achieving students and professionals from around the world apply to the world’s top graduate schools to study business, public policy, law, urban planning, public health, education, and design.

Our signature program is called Application Accelerator®.

As one of my Enrollment Specialists, you would be the first point of contact for prospective clients. Prospective clients will book a free 90-minute Breakthrough Call with you, and your job would be to listen to the potential client’s storyask them lots of questions to understand their strengths, weaknesses, and worries (we’ll give you the questions to ask), and then invite them to work with us if you are 100% confident we can help them solve all of their problems and that they’d be a great fit for working with us. Once you invite them to work with us, you would address their doubts and fears one by one about joining the Application Accelerator®.

To be clear, you don’t need a fancy college or graduate degree to excel in this role, because you would not be the person advising the client on how to apply to graduate school; you would serve as the gatekeeper for our amazing program. You would be helping people cross the bridge of fear, so that they can go from confusion to clarity.

I’m looking to hire, train, and mentor two super-committed people who are passionate, persuasive, energetic, optimistic, committed, and resilient to speak to these eager and excited prospective clients and help me decide if the client is a great fit for our program as well as help the right people commit to working with us on their grad school applications.

If you want to…

  • make great money while making a difference and crafting a fulfilling career on your own terms
  • work from home. We’re a remote team but we meet several mornings per week at 9 am Eastern Time. We work primarily during U.S. business hours of 9 am – 6 pm Eastern Time. You MUST be located in the U.S. for this role.
  • have in-depth conversations with 5 people every day who are excited to talk to you. The calls are about 90 minutes long and are primarily held between 9 am – 6 pm Eastern Time (though we do sometimes conduct calls on nights and weekends to accommodate our clients).
  • do absolutely NO cold calling. The people you’ll be speaking with WANT to speak to you.
  • feel proud of the work you do and the way you are helping change lives
  • work on a fun, collaborative, diverse team
  • receive guidance and mentorship from a successful Harvard Business School & Harvard Kennedy School-educated entrepreneur who will deeply care about your success…
  • work with coworkers who you learn from and love to hang out with virtually and on all-expenses paid team retreats

…Then this position might be for you.

The Art of Applying posing after beating the Escape Game during our January 2018 team retreat

If you are looking for the following things, then this role is NOT for you:

  • a quick way to make some easy cash. This role has high earning potential (our top salesperson earns $6000-$10,000 per month in commissions and he started this job with no sales background in June 2017) but this is NOT a quick and easy way to make money. There is a learning process to this role, and we are here to mentor and coach you, but you have to be committed to learning the structure of our process.
  • the 4-hour workweek or digital nomad lifestyle. This is a remote position, but it is not a role for someone looking to find a job that will launch their digital nomad lifestyle or for someone who wants to work as few hours as possible. This job is for people who are super-committed to being great at the role, earning well while making a difference, and making their long-term personal and professional dreams come true.
  • a way to build your own brand or start your own business. We are not interested in candidates that currently have their own business or plan to one day run their own business. We’re seeking candidates who are interested in the freedom that comes from having a predictable, meaningful, fun, well-paying job.

Apply to join our team if you have these qualities:

  • You are available to work full time (40 hours per week). Our regular hours are Monday – Friday from 9 am – 6 pm ET but this role requires about 12 hours per week of your 40-hour week be conducted after 6 pm or on a weekend to provide night and weekend availability for prospective clients who want a Breakthrough Call with you at night or on a weekend.
  • You can handle working in a lucrative, commission-only role. This job is commission-only employment. What that means is your pay comes from your performance as a salesperson, but that you will never earn less than minimum wage. (We provide health insurance and retirement contribution matching.)
  • You value education. You don’t need fancy degrees for this position, but you cannot be a person who thinks that college or grad school is a waste of time.
  • You are a positive person. You know how to find the good in challenging situations. Hearing “no” or “I need to think about it” several times a day can be discouraging, and you need to be able to bounce back from rejection and bring your full self to the next call.
  • You like persuading people. This is a position where you will get told no or “I need to think about it” a lot. You need to be able to persevere through rejection. This role is great for people who are energized by the challenge of persuading and influencing people.
  • You are a person who follows through on her/his commitments. You don’t jump ship or give up when things get hard.
  • You like speaking on the phone. You know how to connect and communicate well with people you cannot see face-to-face.
  • You like people. You do not have to be an extrovert for this position, but you must like speaking with people (on a 1-on-1 basis), connecting with people, and helping people.
  • You are detail-oriented and methodical. Each call will be with a different person with their own particular story, triumphs, and challenges, but there will be a SCRIPT and a METHOD that you must stick to for EVERY SINGLE CALL.
  • You are an honest person with high integrity. You must be willing to turn people away who are not a good fit for our program, even it means that you won’t get a commission for that sale. Making sure we work with the right people (and not just with anyone) has to be more important to you than making as much money as possible.
  • You have consistent access to reliable internet and a quiet place to work. Our team is remote, so you’ll need your own laptop and reliable internet connection. You’ll also need a quiet and private place (such as a home office) to conduct your calls.

How to apply:

Fill out the application below.

(Note: The question that asks you to upload your DISC profile is REQUIRED. It is just not set as required so that you can send in your DISC results separately if you are having trouble submitting your application without including it.)

Currently accepting applications
(hiring will happen on a rolling basis)

Enrollment Specialist (Sales) Application

  • Take the DISC assessment at this link and report your links in the form on that page in addition to uploading them in this form: http://theartofapplying.com/disc If you have trouble uploading your DISC assessment, you can email it separately to help@theartofapplying.com after taking it at http://theartofapplying.com/disc
    Drop files here or
    Accepted file types: pdf.
  • Drop files here or
    Accepted file types: pdf, doc, docx, pages.
  • Please be as specific as possible. Don't just say "Facebook." If it was on Facebook, who's Facebook post was it?
  • Please be as specific and detailed as possible.
  • What idea / product were you selling? Who were you selling to? What resistance or objections to buying or taking action did the person have? How did you overcome their resistance and objections?
  • Please be as detailed as possible.
  • Tell me about it in detail.
  • Tell me about it in detail.
  • Tell me about it in detail.
  • Please state your desired total compensation per month in USD.


After reading the entire description above, email us at help@theartofapplying.com with any questions.

Want more information?

Read about Kaneisha Grayson, founder of The Art of Applying, here.

Join our free Facebook group to see what our prospective clients and our founder are like. The group includes written Facebook posts as well as video posts from our founder.

KDG Ventures LLC dba The Art of Applying is an equal opportunity employer and does not
discriminate based upon race, color, national origin, religion, sex, sexual orientation, sexual identity, gender identity, disability, medical condition, AIDS/HIV, age, genetic information, marital status, family status, political activities or affiliation, military or veteran status, or status as a victim of domestic violence, assault, or stalking.