We're Hiring A...

Sales Representative (Closer)

This is 100% remote, contract-to-hire role with an OTE of $4,500+ / month. This role will start as a six month contract and if the hire performs well, we'll look to bring them on full time.

Who We Are

At Cultivated Culture, our mission is to teach job seekers a proven system for landing dream jobs that they love without applying online. We aim to provide resources and education that will help job seekers take control of their job search and the roles they land. Today, we serve a community of 1.4M+ job seekers via our free resources, job search tools, one-on-one coaching, and digital courses.

Cultivated Culture was born out of our founder, Austin Belcak’s, personal experience with the job search. He founded Cultivated Culture in 2016 after spending two frustrating years in the traditional job search. Since founding Cultivated Culture, his job search system has been featured in Forbes, Business Insider, Inc, Fast Company, Fortune, and more. He’s also been named a LinkedIn Top Voice & Influencer. You can learn more about Austin and our mission on the company’s About page and his LinkedIn profile.

About This Role

Cultivated Culture is looking to hire a Sales Representative (Closer) to help expand and support our growing coaching business. This role will be a contract-to-hire position. The initial role will be a 6 month contract. If this person excels in their role, we will look to bring them on as a full time employee.

This is a “closer” type of role. The person we hire will be responsible for fielding sales calls with prospective clients and selling them into our career coaching program. The leads will be 100% inbound to start. You will be engaging with prospective clients, connecting with them about their job search needs, educating them on our coaching program, and converting them into coaching clients.

The ideal candidate for this position leads with empathy, warmth, and collaboration when speaking to our prospective clients while bringing enthusiasm, motivation, and hunger for sales internally.

This role will work directly with Austin Belcak, our founder, and Forrest Clements, our Head Career Coach. There are two main components of this role:

1. Sales & Customer Relationship Management - About 70% of the time in this role will be spent engaging with potential coaching clients. These people find and express interest in our coaching program. When they do, they’ll be funneled to you! Your first job is to understand who they are (their personality), what they're struggling with (their pain points), where they want to go (their desired outcome), and what’s stopping them from getting there. 

Your second job is to lead with empathy and authenticity to build a relationship with them, connect with them on those points, and show them how our coaching program can help alleviate their pain points, solve their challenges, and achieve their desired outcomes.

This component of the role will take place over emails and Zoom calls.

2. Sales System Optimization - The remaining 30% of this role will be focused on optimizing the systems we use to engage with, nurture, and close prospective clients. We get a high volume of leads and we use systems to convert them into paid coaching clients. We are heavily data-driven and track outcomes at every step (i.e. Visitor > Form Fill > Discovery Call Booking > Completed Discovery Call > Sale). We leverage specific strategies at each of these stages, but we’re also constantly experimenting with and testing new strategies.

The person we hire will initially focus on becoming a complete expert on our current system. After that, you will focus on helping us track numbers, identify gaps, generate creative / innovative solutions, and test them in real time.

Training & Onboarding

This role has an estimated six week training period. You’ll be paid at your assumed 100% quota rate for that six week period. You’ll be trained by both Austin (our Founder) and Forrest (our Head Career Coach). When you start, you’ll meet with both Austin and Forrest regularly as you progress through your training.

Initially, you will focus on learning the ins and outs of our job search system. You’ll go through our flagship course and shadow Forrest and Austin on client calls to get a sense of how we approach the job search and help our clients. This should take about 2 weeks.

Next, you’ll focus on the sales process for our coaching program. We’ll walk you through the system we have and you’ll continue to shadow Forrest and Austin on sales calls. This should take about 2 weeks. 

As you get comfortable, we’ll start having you run point on a small set of our Career Clarity Calls with Forrest and Austin shadowing. Then we’ll increase the call volume and reduce the shadowing as you ramp up into the role. This should take about 2-3 weeks. After six weeks total, you'll be managing 80%+ of the sales calls while ramping to 100% over the next 2 weeks.

During each of these phases, you will have regular check ins with Forrest and Austin where you can ask questions, get clarity, and ensure you have all the support you need to be successful in this role! Finally, the timelines mentioned above are estimates - sometimes things take a bit longer and that’s totally fine.

The Ideal Candidate (Minimum Requirements)

  • Has 2+ years of professional experience (internships included!)
  • Is motivated by a sales role (where earning potential isn’t capped as is based on performance, but is based on closing deals)
  • Leads with empathy, authenticity, and kindness
  • Has excellent “people skills” (you enjoy engaging with people and you have the ability to understand, empathize with, and motivate them)
  • Has excellent communication skills (you are organized and diligent with your communication, you know how to communicate in a way that reduces back and forth and makes things clear the first time)
  • Is Creative! You aren’t afraid to step outside of the traditional process to come up with solutions that will help your clients succeed
  • Is Persistent - you don’t give up after one “No.” Instead, you stay politely persistent and dig deeper to find solutions and generate outcomes
  • Has a proactive mindset - when you see a problem you work to build a solution instead of waiting for others to notice and fix things

Extra Awesome, But Optional Qualifications

  • Has direct sales experience (closer experience is a big plus)
  • Has experience with sales systems and tools (CRMs, sales best practices, etc)
  • A deliverable that goes above and beyond a resume or online application to illustrate why you’re a great fit for this role (videos, pitch deck, or other Value Validation Projects are good examples)

Who This Job Is NOT For

This job is not for people who are:

  • Only in it for the commission
  • Aggressive sellers
  • Not passionate about helping people accelerate their careers

Everyone works for money, and we completely get that. But we’ve found that our business is most successful when we focus on our prospective clients and treat them with empathy, warmth, and a consultative approach.

We’re not looking for aggressive or pushy sellers and / or sellers who are only in it to make a commission. Instead, we’re looking for people with a passion for helping others succeed, the ability to empathize with their situation, and the knowledge that combining both of those things will led to exceeding their personal earnings targets.

Perks Of This Job

  • 100% remote (in the United States across EST, CST, MST, or PST time zones)
  • Work when you want - as long as goals are being met, you create your schedule
  • Commission structure with no limit on your earnings
  • Direct path to Full Time role


The compensation for this role is on a per-close basis. You'll be paid a specific dollar amount for every lead that your convert into a sale.

The average On Target Earnings (OTE) for this role is $4,500+ / month. This number is based on expected sales numbers, but there is no limit to the amount of commission you can earn other than the number of clients we’re able to fulfill on the coaching side each month. If you’re able to close leads above estimates, you’ll earn more!

If we hit targets and decide to turn the role into a full time hire, we can revisit the compensation structure together and find a fit that works best based on what we learned from the 6 month contract.

As mentioned above, you will be paid at a rate of $4,500 / month during your six week training period. After six weeks, you will move onto the normal compensation plan associated with the role.

What To Expect From The Hiring Process

Transparency is a core value for us at Cultivated Culture. We want you to know exactly what this process will look like when you apply. Here is what you can expect:

Step #1: After applying, give our team 10 business days to reply to your application. If you’re not a fit, we’ll send you an email letting you know. If you are a fit, we’ll send you an email with instructions for the next round.

Step #2: The next round will be a 45 minute conversation with Austin, our founder.

Step #3: We’ll send you a short, paid assessment to complete. This assessment will have a few exercises to gauge your capabilities as they align with the role’s requirements. We will pay you the time it takes to complete the assessment at the same estimated hourly route as the role.

Step #4: A 30 minute conversation with Forrest, our Head Career Coach

Step #5: Hiring decision made!

Our expectation is for all of this to happen in a 6 week time frame, barring any unforeseen circumstances on our side or yours.

Note: Applicants must be eligible to work in the United States (we are unable to offer visa sponsorship at this point in time).